- Activated charcoal-mediated synthesis of chalcones catalyzed by NaOH in water
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A variety of chalcones were synthesized in good yields by the activated charcoal-mediated aldol reactions between benzaldehydes and acetophenones catalyzed by NaOH in water. 2,6-Bis((E)-benzylidene)cyclohexan-1-ones were prepared by the aldol reactions between benzaldehydes and cyclohexanone. Activated charcoal could be recycled five times without the significant decrease of yields.
- Tanemura, Kiyoshi,Rohand, Taoufik
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supporting information
(2021/02/27)
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- Mechanochemical Syntheses of N-Containing Heterocycles with TosMIC
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A mechanochemical van Leusen pyrrole synthesis with a base leads to 3,4-disubstitued pyrroles in moderate to excellent yields. The developed protocol is compatible with a range of electron-withdrawing groups and can also be applied to the synthesis of oxazoles. Attempts to mechanochemically convert the resulting pyrroles into porphyrins proved to be difficult.
- Bolm, Carsten,Molitor, Claude,Rissanen, Kari,Schumacher, Christian,Smid, Sabrina,Truong, Khai-Nghi
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p. 14213 - 14222
(2021/09/07)
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- In silico studies, nitric oxide, and cholinesterases inhibition activities of pyrazole and pyrazoline analogs of diarylpentanoids
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A new series of pyrazole, phenylpyrazole, and pyrazoline analogs of diarylpentanoids (excluding compounds 3a, 4a, 5a, and 5b) was pan-assay interference compounds-filtered and synthesized via the reaction of diarylpentanoids with hydrazine monohydrate and phenylhydrazine. Each analog was evaluated for its anti-inflammatory ability via the suppression of nitric oxide (NO) on IFN-γ/LPS-activated RAW264.7 macrophage cells. The compounds were also investigated for their inhibitory capability toward acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), using a modification of Ellman's spectrophotometric method. The most potent NO inhibitor was found to be phenylpyrazole analog 4c, followed by 4e, when compared with curcumin. In contrast, pyrazole 3a and pyrazoline 5a were found to be the most selective and effective BChE inhibitors over AChE. The data collected from the single-crystal X-ray diffraction analysis of compound 5a were then applied in a docking simulation to determine the potential binding interactions that were responsible for the anti-BChE activity. The results obtained signify the potential of these pyrazole and pyrazoline scaffolds to be developed as therapeutic agents against inflammatory conditions and Alzheimer's disease.
- Mohd Faudzi, Siti Munirah,Leong, S. Wei,Auwal, Faruk A.,Abas, Faridah,Wai, Lam K.,Ahmad, Syahida,Tham, Chau L.,Shaari, Khozirah,Lajis, Nordin H.,Yamin, Bohari M.
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- Curcumin-cinnamaldehyde hybrids as antiproliferative agents against women’s cancer cells
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Curcumin and cinnamaldehyde are natural products whose antineoplastic activity has been well explored in biological evaluations. However, their poor chemical stability under physiological conditions has been an obstacle to their use as therapeutic agents. Herein, we designed and synthesized two series of curcumin-cinnamaldehyde hybrids by removing reactive functionalities, including β-diketone and aldoxyl moieties. All compounds were evaluated by the MTT assay to determine their antiproliferative activity against women’s cancer cells. Compound 5a (3′-hydroxychalcone) demonstrated potent antiproliferative activity against all cancer cell lines tested, with IC50 values ranging from 2.7 to 36.5 μM. Compound 5a was more active and selective than curcumin and cinnamaldehyde (parent compounds) against the CaSki, SiHa, C33, and A431 cell lines, displaying a higher selectivity index (SI = 8.5) than curcumin (SI = 0.8) toward the non-tumorigenic HaCaT cell line. Clonogenic experiments indicated that compound 5a inhibited A431 colony formation in a concentration-dependent manner. In addition, 5a was more stable than its parent compounds in pH 7.4 at 37 °C. In silico investigations suggested that 5a has good drug-likeness properties. In conclusion, our results indicate the use of curcumin and cinnamaldehyde as parent compounds for the design of hybrids with attractive antiproliferative activity and chemical stability.
- Anselmo, Daiane B.,Polaquini, Carlos R.,Marques, Beatriz C.,Ayusso, Gabriela M.,Assis, Letícia R.,Torrezan, Guilherme S.,Rahal, Paula,Fachin, Ana L.,Calmon, Marília F.,Marins, Mozart A.,Regasini, Luis O.
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p. 2007 - 2015
(2021/08/31)
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- Fluorescent Molecular Logic Gates Driven by Temperature and by Protons in Solution and on Solid
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Temperature-driven fluorescent NOT logic is demonstrated by exploiting predissociation in a 1,3,5-trisubstituted Δ2-pyrazoline on its own and when grafted onto silica microparticles. Related Δ2-pyrazolines become proton-driven YES an
- West, Matthew E. S.,Yao, Chao-Yi,Melaugh, Gavin,Kawamoto, Kyoko,Uchiyama, Seiichi,de Silva, A. Prasanna
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supporting information
p. 13268 - 13274
(2021/08/06)
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- Palladium-Catalyzed Aminomethylation of Nitrodienes and Dienones via Double C—N Bond Activation
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A new strategy for the generation of the active Pd-alkyl species from aminal via C—N bond activation has been established, in which the formation of zwitterionic intermediate through aza-Michael addition of aminal to nitrodienes or dienones is identified as a key step for the activation of the C—N bond. The efficient strategy has enabled a new palladium-catalyzed α-aminomethylation of nitrodienes and dienones via double C—N bond activation. The scope and versatility of the reaction were demonstrated and a broad range of substrates bearing electron-donating and -withdrawing groups on the aromatic rings were all compatible with this reaction to furnish the desired α-aminomethylated products in moderate to good yields with excellent regioselectivities and E/Z selectivities.
- Yu, Bangkui,Gao, Bao,Zhang, Xuexia,Zhang, Haocheng,Huang, Hanmin
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supporting information
p. 566 - 570
(2021/02/01)
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- Bu4NHSO4-Catalyzed Direct N-Allylation of Pyrazole and its Derivatives with Allylic Alcohols in Water: A Metal-Free, Recyclable and Sustainable System
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Allylic amines are valuable and functional building blocks. Direct N-allylation of pyrazole and its derivatives as an atom economic strategy to provide allylic amines has been achieved only using commercial Bu4NHSO4 as the metal-free catalyst and water as the solvent without any additives. 11–93% isolated yields were obtained for the N-allylation of pyrazole and its derivatives with allylic alcohols. Bu4NHSO4 could be reused for six times by simple extraction nearly without loss of catalytic activity and was also suitable for a gram-scale production. The reaction of allylic ether and pyrazole did not occur to give the desired product indicated that allylic ether was not the active intermediate in the pathway. Density functional theory (DFT) calculations reveal that there are hydrogen bonding effects among substrates, solvent and catalyst, especially the one formed between allylic alcohol and H2O. Control experiments in different protic solvents further demonstrate the intermolecular hydrogen bonding of allylic alcohol and water. (Figure presented.).
- Zhuang, Hongfeng,Lu, Nan,Ji, Na,Han, Feng,Miao, Chengxia
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supporting information
p. 5461 - 5472
(2021/09/29)
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- Ligand-Free Palladium-Catalyzed Carbonylative Suzuki Couplings of Vinyl Iodides with Arylboronic Acids under Substoichiometric Base Conditions
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A ligand-free palladium-catalyzed carbonylation of vinyl iodides with arylboronic acids, permitting the synthesis of chalcones and α-branched enones, has been established. This reaction proceeds smoothly at ambient pressure and temperature, and works well even with a substoichiometric amount of base. Importantly, this mild, efficient, and operationally simple protocol is suitable for the late-stage functionalization of an epiandrosterone-derived complex molecule.
- Yang, Zhiyuan,Gong, Pei-Xue,Chen, Junjie,Zhang, Jie,Gong, Xu,Han, Wei
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supporting information
p. 1207 - 1212
(2021/06/18)
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- Anti-corrosive property of bioinspired environmental benign imidazole and isoxazoline heterocyclics: A cumulative studies of experimental and DFT methods
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In the present study, four imidazoline (IDZ) and four isoxazolines (ISO) heterocyclics differing in the nature of methoxy (-OCH3) and aromatic (phenyl and naphthyl) moieties are synthesized, characterized and evaluated as corrosion inhibitors for mild steel in acidic solution of 1 M HCl. Results showed that imidazoline based heterocyclic compounds are better corrosion inhibitors than isoxazoline based heterocyclics and both classes of compounds showed inhibition efficiency of more than 85% at 20 mgL?1 concentration. Results further showed that inhibitors containing methoxy, phenyl, and naphthyl moieties showed higher protection efficiency as compared to the inhibitors without these moieties. PDP Study revealed that investigated IDZs and ISOs acted as mixed type inhibitors and their adsorption on the metallic surface followed the Langmuir adsorption isotherm model. All the experimental results were corroborated by density function theory (DFT) based quantum chemical calculations. Numerous DFT based indices calculated for neutral as well as protonated forms of the IDZs and ISOs in order to get better insight about metal-IDZs/ISOs interactions. Outcomes of the DFT analysis showed that protonated (cationic) form of the all the inhibitors are more strongly adsorbed on the metallic surface as compared to their neutral form.
- Ramkumar, Sowmya,Nalini,Quraishi, Mumtaz A.,Ebenso, Eno E.,Verma, Chandrabhan
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supporting information
p. 103 - 119
(2019/12/24)
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- Highly Enantioselective Epoxidation of α,β-Unsaturated Ketones Using Amide-Based Cinchona Alkaloids as Hybrid Phase-Transfer Catalysts
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A series of 20 one chiral epoxides were obtained with excellent yields (up to 99%) and enantioselectivities (up to >99% ee) using hybrid amide-based Cinchona alkaloids. Our method is characterized by low catalyst loading (0.5 mol %) and short reaction times. Moreover, the epoxidation process can be carried out in 10 cycles, without further catalyst addition to the reaction mixture. This methodology significantly enhance the scale of the process using very low catalyst loading.
- Jurczak, Janusz,Majdecki, Maciej,Tyszka-Gumkowska, Agata
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supporting information
(2020/11/13)
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- Relay Catalysis to Synthesize β-Substituted Enones: Organocatalytic Substitution of Vinylogous Esters and Amides with Organoboronates
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Organocatalysis was shown to facilitate conjugate additions to vinylogous esters and amides for the first time. Subsequent elimination of a β-alcohol or amine provided π-conjugated β-substituted enones. Remarkably, nucleophile addition to the electron-rich vinylogous substrates is more rapid than classical enones, forming monosubstituted products. A doubly organocatalytic (organic diol and methyl aniline) conjugate addition synthesized the products directly from alkynyl ketones. Both of these catalytic transformations are orthogonal to transition metal catalysis, allowing for good yields, easily accessible or commercially available reagents, high selectivity, reagent recovery and recyclability, facile scalability, and exceptional functional group tolerance.
- Sundstrom, Sasha,Nguyen, Thien S.,May, Jeremy A.
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p. 1355 - 1359
(2020/02/13)
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- Some 1,3,5-trisubstituted pyrazoline derivatives targeting breast cancer: Design, synthesis, cytotoxic activity, EGFR inhibition and molecular docking
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Different 1,3,5-trisubstituted pyrazoline derivatives 2a-c, 3-c, 4a-f, 6a-c, 7a-f and 8a-d were prepared via condensation reaction of the appropriate chalcone 1a-c or 5a-c with various hydrazine derivatives. All compounds were screened for their cytotoxicity against breast MCF-7 cancer cell line and the normal fibroblasts WI-38. Thirteen compounds 2a, 3a, 3c, 4a-d, 6c, 7d, 7e, 8b, 8d and 8f revealed promising cytotoxicity against MCF-7 compared to the reference standard staurosporine and they were safe to the normal fibroblasts WI-38. In addition, compounds 3c, 6c, 7d, 8b and 8d elicited higher cytotoxicity than erlotinib and exhibited promising EGFR inhibitory activity at submicromolar level comparable to that of erlotinib except for compound 8b that may exert its cytotoxicity via another mechanism besides EGFR inhibition. Molecular docking of 3c, 6c, 7d, 8b and 8d in the active site of EGFR confirmed the obtained results.
- El Kerdawy, Ahmed M.,El-Ansary, Dina Y.,George, Riham F.,Kandeel, Manal
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supporting information
(2020/03/31)
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- Efficient catalytic performance of calcined tungstophosphoric acid for the Claisen-Schmidt condensation under solvent-free reaction
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Effect of calcination of tungstophosphoric acid catalyst was evaluated in terms of the synthesis of chalcone derivatives via Claisen-Schmidt condensation using the reaction of acetophenone and several substituted aldehydes. The catalyst was characterized before and after calcination by FT-IR to assess the effectiveness of the synthesis of the desired products. The calcined tungstophosphoric acid catalyst (HPW-CL) showed a better performance and high yield of Claisen-Schmidt products in a short period of time. It was also found out that the calcined tungstophosphoric acid provides a chemo selective, efficient and environmentally benign synthesis of chalcone in an excellent yield in a solvent-free system.
- Alharthi, Abdulrahman I.
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p. 2579 - 2584
(2019/10/02)
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- Rh(II)-Catalyzed Nitrene-Transfer [5 + 1] Cycloadditions of Aryl-Substituted Vinylcyclopropanes
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Formal [5 + 1] cycloadditions between aryl-substituted vinylcyclopropanes and nitrenoid precursors are reported. The method, which employs Rh2(esp)2 as a catalyst, leads to the highly regioselective formation of substituted tetrahydropyridines. Preliminary mechanistic studies support a stepwise, polar mechanism enabled by the previously observed Lewis acidity of Rh-nitrenoids. Overall, this work expands the application of nitrene-transfer cycloaddition, a relatively underexplored approach to heterocycle synthesis, to the formation of six-membered rings.
- Combee, Logan A.,Johnson, Shea L.,Laudenschlager, Julie E.,Hilinski, Michael K.
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supporting information
p. 2307 - 2311
(2019/04/10)
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- Synthesis method of dienal or dienone compound
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The invention discloses a synthesis method of a dienal or dienone compound. The method comprises subjecting olefin aldehyde or ketene adopted as a starting raw material to one-step dehydrogenation ina polar organic solvent to obtain a (E,E)-dienal or (E,E)-dienone compound, by adopting a palladium compound as a catalyst, adopting oxygen as an oxidant and adopting trifluoroacetic acid as an additive. The method provided by the invention realizes synthesis of (E,E)-dienal and (E,E)-dienone compounds with single three-dimensional configuration through oxidative dehydrogenation catalyzed by a transition metal, and compared with traditional methods, the method has the advantages of cheap and easily available raw materials, simple operation, a wider substrate application range, higher reactionefficiency, environmental friendliness, a high yield and a high atom utilization rate.
- -
-
Paragraph 0017; 0018
(2019/12/02)
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- Alpha, beta unsaturated ketone compound and preparation method and application thereof
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The invention belongs to the technical field of organic synthesis, and in particular relates to an alpha, beta unsaturated ketone compound and a preparation method and application thereof. The methodcomprises the following steps: dissolving a compound of
- -
-
Paragraph 0103-0109
(2019/09/10)
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- Intermolecular Multiple Dehydrogenative Cross-Couplings of Ketones with Boronic Acids and Amines via Copper Catalysis
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An efficient and versatile oxidative coupling reaction was developed for the synthesis of valuable β-functionalized unsaturated ketones and meta-substituted phenols. In the case of intramolecular reactions, achieving rapid molecular complexity through multiple dehydrogenative couplings is already a well-established strategy. Herein, we report an intermolecular multiple dehydrogenative coupling between ketones and nucleophilic amines or boronic acids using inexpensive copper(I) oxide as a catalyst. This method provides a facile access to highly desirable chemical products such as α,β-unsaturated ketones, enaminones, and synthetically relevant meta-substituted phenols. (Figure presented.).
- Wang, Tianzhang,Chen, Guowei,Lu, Yu-Jing,Chen, Qian,Huo, Yanping,Li, Xianwei
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supporting information
p. 3886 - 3892
(2019/07/19)
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- Acyl/aroyl Meldrum's acid as an enol surrogate for the direct organocatalytic synthesis of α,β-unsaturated ketones
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The operationally simple, robust and straightforward organocatalytic protocol is developed for the synthesis of E-selective α,β-unsaturated ketones. The method utilizes simple and easily accessible starting materials such as Meldrum's acid, carboxylic acid, aldehyde and simple bifunctional amine catalyst. The tandem organocatalytic process utilizes acyl/aroyl Meldrum's acid as an enol surrogate for the effective Doebner-Knoevenagel type condensation reactions. A wide variety of aldehydes, carboxylic acids and base sensitive functional groups are well tolerated under the mild reaction conditions.
- Khopade, Tushar M.,Warghude, Prakash K.,Mete, Trimbak B.,Bhat, Ramakrishna G.
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p. 197 - 200
(2018/12/13)
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- Design, synthesis and biological evaluation of novel dihydropyrimidine-2-thione derivatives as potent antimicrobial agents: Experimental and molecular docking approach
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Introduction: Dihydropyrimidine scaffold represent an important class of pharmacologically active nitrogen containing heterocyclic compounds. A wide range of molecules with dihydropyrimidine moieties have important role in medicinal chemistry on account of their potential biological activities. Methodology: A series of 3,4-dihydropyrimidine-2(1H)-thione derivatives have been designed and synthesized in a concise way through condensation of variously substituted chalcones with thiourea in alkaline alcoholic solutions. In order to investigate their biological significance, these compounds were tested for their in vitro antimicrobial potential against various bacterial and fungal strains. Moreover, the experimental results were supported by molecular docking studies. Results and Discussion: The newly synthesized compounds were characterized by the usual spectroscopic techniques In case of antibacterial activity, the compounds 5 (40.3±0.44 mm), 12 and 13 (almost 35 mm) exhibited highest zone of inhibitions against Methicillin-resistant Staphylococcus auerus (MRSA) bacterial strain as compared to the standard drug Cefixime. These compounds displayed moderate to good activities against all attempted fungal strains. In docking analysis, it has been observed that compounds 8 (-6.4017 Kcal/mol) and 10 (-6.1319 Kcal/mol) revealed significant binding affinity against penicillin binding protein (PDB ID: 1VQQ), while compounds 1 (-143.23 Kcal/mol) and 2 (-146.99 Kcal/mol) showed best activity for shikimate dehydrogenase (PDB ID: 3DON). Conclusion: In conclusion, we have designed, synthesized and characterized an interesting series of biologically active dihydropyrimidine derivatives. Remarkably, most of the synthesized compounds were found more active against all tested bacterial strains in comparison to the standard drug Cefixime as manifested by experimental as well as theoretical results.
- Mughal, Ehsan Ullah,Sadiq, Amina,Hamayun, Muhammad,Zafar, Muhammad Naveed,Fatima, Nighat,Yameen, Muhammad Arfat,Muhammad, Syed Aun,Mumtaz, Amara,Ahmed, Ishtiaq,Fatima, Tehseen
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p. 1189 - 1201
(2018/11/01)
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- High pressure-assisted low-loading asymmetric organocatalytic conjugate addition of nitroalkanes to chalcones
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The application of high pressure (up to 9 kbar) allows for relatively fast (1-5 h) and highly enantioselective 1,4-addition of nitromethane and 2-nitropropane to chalcones at room temperature with substantial reduction of catalyst loading (0.2-1 mol% of cinchona alkaloid-based thioureas and squaramides). Various γ-nitroketones were obtained at 9 kbar with high yield and enantioselectivity (up to 98%), whereas in control experiments at atmospheric pressure usually only a small amount (10%) of products were formed after 20 h.
- Cholewiak, Agnieszka,Adamczyk, Kamil,Kopyt, Micha?,Kasztelan, Adrian,Kwiatkowski, Piotr
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supporting information
p. 4365 - 4371
(2018/06/22)
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- One-Pot Synthesis of α,β-Unsaturated Esters, Ketones, and Nitriles from Alcohols and Phosphonium Salts
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A general method for the synthesis of α,β-unsaturated esters, ketones, and nitriles is successfully achieved by a one-pot copper-catalyzed oxidation with O 2 in air as oxidant. The solvent mixture of acetonitrile and formamide (1:1) is optimized to ensure the oxidation of alcohols, deprotonation of phosphonium salt, and Wittig reaction occur efficiently in one pot. A broad range of substrates has been explored for this process, including three electron-withdrawing group (CO 2 Et, COPh, CN) functionalized phosphonium salts. They reacted not only with benzylic and heteroaromatic alcohols, but also with aliphatic alcohols, forming the corresponding α,β-unsaturated esters, ketones, and nitriles in moderate to excellent yields.
- Ding, Weijie,Hu, Juan,Jin, Huile,Yu, Xiaochun,Wang, Shun
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p. 107 - 118
(2017/09/28)
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- A robust multifunctional ligand-controlled palladium-catalyzed carbonylation reaction in water
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A novel, hydrophilic and recyclable methoxypolyethylene glycol (PEG)-modulated s-triazine-based multifunctional Schiff base/N,P-ligand L9 was prepared and used in Pd-catalyzed Heck-type carbonylative coupling reactions, affording diverse chalcone derivatives and 1,4-dicarbonyl esters in good yields.
- Gao, Pei-Sen,Zhang, Kan,Yang, Ming-Ming,Xu, Shan,Sun, Hua-Ming,Zhang, Jin-Lei,Gao, Zi-Wei,Zhang, Wei-Qiang,Xu, Li-Wen
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supporting information
p. 5074 - 5077
(2018/05/26)
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- Antibacterial & antitubercular activities of cinnamylideneacetophenones
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Cinnamaldehyde is a natural product with broad spectrum of antibacterial activity. In this work, it was used as a template for design and synthesis of a series of 17 cinnamylideneacetophenones. Phenolic compounds 3 and 4 exhibited MIC (minimum inhibitory
- Polaquini, Carlos R.,Torrezan, Guilherme S.,Santos, Vanessa R.,Nazaré, Ana C.,Campos, Débora L.,Almeida, Laíza A.,Silva, Isabel C.,Ferreira, Henrique,Pavan, Fernando R.,Duque, Cristiane,Regasini, Luis O.
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supporting information
(2017/11/07)
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- Iridium-catalysed desilylative acylation of 1-alkenylsilanes
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We report the iridium-catalysed desilylative acylation of styryl and dienyl silanes by acid anhydrides to afford (E)-α,β-unsaturated ketones. The [{Ir(μ-Cl)(cod)}2] catalyst is the first non-rhodium complex successfully applied for this type of
- Zaranek, Maciej,Skrodzki, Maciej,Szudkowska-Fr?tczak, Justyna,Dodot, Maciej,Kownacki, Ireneusz,Orwat, Bartosz,Pawlu?, Piotr
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- Carbon-carbon bond formation in acid deep eutectic solvent: Chalcones synthesis: Via Claisen-Schmidt reaction
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One of the most studied properties of novel organic solvents is represented by their use as media for many chemical reactions. In this field Ionic Liquids (ILs) and more recently Deep Eutectic Solvents (DESs) have been playing significant roles for their smart properties. DESs are increasing their relevance thanks to their low toxicity, and because of their simple and cheap preparation that can be carried out by simply mixing two compounds. In this work we present the studies of the use of an acid DES obtained from 3-(cyclohexyldimethylammonio)propane-1-sulfonate and (1S)-(+)-10-camphorsulfonic acid (SB3-Cy/CSA) as reaction media and catalyst for carbon-carbon bond formation reaction via Claisen-Schmidt condensation. This powerful and widely used aldol condensation was performed without the use of any catalysts that are usually needed in this reaction, because of the presence of acid CSA in the DES components. We synthesised fourteen substituted chalcones from benzaldehydes and substituted benzaldehydes in combination with acetophenone and substituted acetophenones as probe reactions. The advantages of the use of this DES in this relevant reaction are represented by: the green properties of the media and its low toxicity; the absence of harmful acids to catalyse the aldol condensation because of the camphorsulfonic acid composing the DES mixture; the recycling and the re-use of the DES in subsequent reaction cycles; the mild conditions and the excellent conversions and yields observed.
- Tiecco, Matteo,Germani, Raimondo,Cardellini, Fabio
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p. 43740 - 43747
(2016/05/24)
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- Highly regioselective introduction of aryl substituents via asymmetric 1,4-addition of boronic acids to linear α,β,γ,δ-unsaturated ketones
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An efficient palladium(II)-catalyzed regioselective asymmetric 1,4-conjugate addition of arylboronic acids to linear α,β,γ,δ-unsaturated ketones is developed using phosphapalladacycle catalysts. The relevant 1,4-products were obtained exclusively with per
- Gan, Kennard,Ng, Jia Sheng,Sadeer, Abdul,Pullarkat, Sumod A.
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supporting information
p. 254 - 258
(2016/01/20)
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- Asymmetric 1,4-Conjugate Addition of Diarylphosphines to α,β,γ,δ-Unsaturated Ketones Catalyzed by Transition-Metal Pincer Complexes
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An enantioselective asymmetric 1,4-addition of diarylphosphines to linear α,β,γ,δ-unsaturated dienones was developed. A series of chiral PCP- and PCN-transition-metal (Pd, Pt and Ni) pincers, themselves prepared catalytically via asymmetric hydrophosphination, were sequentially screened to reveal the roles of backbone architecture and metal ion in catalyst design. The selected ester-functionalized PCP-palladium pincer afforded the chiral 1,4-phosphine adducts in excellent yields with up to >99% ee. The same catalyst when utilized for the hydrophosphination of an α,β,γ,δ-unsaturated malonate ester also revealed the critical role played by the ester functionality on the ligand backbone in dictating the enantioselectivity of the 1,6-adduct.
- Yang, Xiang-Yuan,Tay, Wee Shan,Li, Yongxin,Pullarkat, Sumod A.,Leung, Pak-Hing
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supporting information
p. 5196 - 5201
(2015/11/09)
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- Synthesis, biological evaluation and QSAR studies of diarylpentanoid analogues as potential nitric oxide inhibitors
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A series of forty-five 1,5-diphenylpenta-2,4-dien-1-one analogues were synthesized and evaluated for their nitric oxide (NO) inhibition activity in IFN-γ/LPS-activated RAW 264.7 cells. Compounds 3h, 7a, 7d and 7e exhibited comparable or significantly higher activity than the standard, curcumin (IC50 = 14.69 ± 0.24 μM). Compound 7d, a 5-methylthiophenyl-bearing analogue, displayed the most promising NO-inhibitory activity with an IC50 value of 10.24 ± 0.62 μM. The 2D and 3D QSAR analyses performed revealed that a para-hydroxyl group on ring B and an α,β-unsaturated ketone moiety on the linker are crucial for a remarkable anti-inflammatory activity. Based on ADMET and TOPKAT analyses, compounds 3h, 7a and 7d are predicted to be nonmutagenic and to exhibit high blood-brain barrier (BBB) penetration, which indicates that they are potentially effective drug candidates for treating central nervous system (CNS) related disorders.
- Mohd Faudzi,Leong,Abas,Mohd Aluwi,Rullah,Lam,Ahmad,Tham,Shaari,Lajis
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p. 1069 - 1080
(2015/06/25)
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- Synthesis, antimicrobial and cytotoxic activity of novel 1,5 benzodiazepine derivatives
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In the present study, a series of novel 2-(substituted phenyl)-3-styryl-2,3-dihydro- 1H-benzo [b] [1,4] diazepines (1-12) has been synthesized from 1,5-(disubstituted phenyl)-2,4-pentadien-1-ones (1a-12a). 1,5-(disubstituted phenyl)-2,4-pentadien-1-ones were prepared by condensing cinnamaldehyde with various aromatic ketones in the presence of 20% NaOH as base. Different 1,5-(disubstituted phenyl)-2,4-pentadien-1-ones on cyclisation with o-phenylene diamine in the presence of NaOH as base resulted in 2-(substituted phenyl)-3-styryl-2,3-dihydro-1H-benzo [b] [1,4] diazepine derivatives. The structures of the newly synthesized compounds were characterized by elemental analysis, IR, 1H NMR and mass spectroscopic studies. All titled compounds were screened for their antimicrobial and cytotoxic activities. Most of the compounds showed promising cytotoxic, antibacterial and antifungal activities.
- Bhat, K. Ishwar,Kumar, Abhishek,Prathyusha
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p. 161 - 164
(2019/01/16)
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- Further studies on anti-invasive chemotypes: An excursion from chalcones to curcuminoids
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In our ongoing search for new anti-invasive chemotypes, we have made an excursion from previously reported potent 1,3-diarylpropenones (chalcones) to congeners bearing longer linkers between the aromatic moieties. Nine 1,ω-diarylalkenones, including curcumin and bisdemethoxycurcumin, were evaluated in the chick heart invasion assay. Unfortunately, these compounds proved less potent and more toxic than earlier evaluated chemotypes. In the 1,3-diarylpenta-2,4-dien-1-one series, fluoro and/or trimethoxy substitution caused an increase in potency. This agrees with observations made earlier for the chalcone class.
- Roman, Bart I.,De Ryck, Tine,Verhasselt, Sigrid,Bracke, Marc E.,Stevens, Christian V.
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p. 1027 - 1031
(2015/02/19)
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- Chemoselective biohydrogenation of α,β- and α,β,γ,δ-unsaturated ketones by the marine-derived fungus Penicillium citrinum CBMAI 1186 in a biphasic system
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To broaden the range of applicability of a reduction reaction mediated by the marine fungal strain Penicillium citrinum CBMAI 1186 to organic chemical processes, the ability of whole mycelia to grow in biphasic mixtures with organic solvents was tested with acetone, ethyl acetate, n-butanol, dichloromethane, n-hexane and toluene. n-Hexane was the least toxic solvent according to the amount of mycelial mass grown in an artificial sea water medium mixed with each solvent. Therefore, whole hyphae of P. citrinum CBMAI 1186 were used as biocatalysts in the chemoselective biotransformation of the carbon-carbon double bond in α,β-, di-α,β-, and mono-α,β,γ,δ-unsaturated ketones (3a, 3c-f) in a biphasic system of phosphate buffer and n-hexane (9:1). Only the di-α,β,γ,δ-unsaturated ketone (3b) was not biocatalyzed under these conditions. In general, there were good conversions of saturated ketones by the enoate reductase enzymes of P. citrinum CBMAI 1186.
- Ferreira, Irlon M.,Meira, Eloá B.,Rosset, Isac G.,Porto, André L.M.
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- Ruthenium-catalyzed conjugate hydrogenation of ?±,?2-enones by in situ generated dihydrogen from paraformaldehyde and water
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Notwithstanding that the highly selective hydrogenation of ?±,?2-enones to allylic alcohols can be realized by using Noyori's Ru bifunctional system, the selective reduction of the C=C bonds in ?±,?2-enones without touching the C=O bonds still lacks a general, simple, and efficient procedure. Ruthenium-catalyzed conjugate hydrogenation of various ?±,?2-enones to saturated ketones with high selectivity was investigated. The most important feature of this procedure was that hydrogen in situ generated from paraformaldehyde (or formalin) and water was employed as the reductant.
- Li, Wanfang,Wu, Xiao-Feng
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supporting information
p. 331 - 335
(2015/03/05)
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- Synthesis and biological activity of 4-aryl-3-benzoyl-5- phenylspiro[pyrrolidine-2.3′-indolin]-2′-one derivatives as novel potent inhibitors of advanced glycation end product
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Diabetic complications and their detrimental effects caused by sugar derived substances, have been the serious issue for the last few years and have yet not been fully combated. The key point of the present study is to synthesize some newer chemical entities which can eradicate such ailments to the maximum possible extent. So with this aim synthesis of some biologically interesting spiro-indolone-pyrrolidine derivatives was accomplished by 1,3-dipolar cycloaddition reaction of azomethine ylide 6 generated in situ from isatin and benzyl amine with the substituted α,β-unsaturated carbonyl compounds 3 as dipolarophile, leading to the formation of new 4-aryl-3-benzoyl-5- phenylspiro[pyrrolidine-2.3′-indolin]-2′-one derivatives 7 stereoselectively in excellent yields. The synthesized compounds have been screened for their advanced glycation end (AGE) product formation inhibitory activity on the basis of their ability to inhibit the formation of AGEs in the bovine serum albumin (BSA)-glucose assay and have been found to exhibit significant activity against AGE formation.
- Kaur, Anjandeep,Singh, Baldev,Vyas, Bhawna,Silakari, Om
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p. 282 - 289
(2014/05/06)
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- Synthesis, characterization and biological activity studies of some substituted pyrimidine derivatives
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A new series of substituted 1-phenyl-3-styryl-4,5-dihydo-1H-pyrazoles (TP1-TP9) has been synthesized by the cyclisation of chalcones with phenyl hydrazine and glacial acetic acid and substituted 4-styryl-pyrimidin-2-ols (LP1-LP9) have been synthesized by the condensation of chalcones with urea in the presence of 40% NaOH as a base. The intermediate substituted 1,5-diphenylpenta-2,4-dien-1-ones were synthesized by condensing cinnamaldehyde with various substituted aromatic ketones in presence of 20% NaOH. The title compounds obtained were characterized by IR, 1H NMR, mass spectral data and were screened for antimicrobial, anticancer and antitubercular activity.
- Ishwar Bhat,Kumar, Abhishek,Thara,Kumar, Pankaj
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p. 271 - 276
(2019/01/21)
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- One-pot synthesis of cinnamylideneacetophenones and their in vitro cytotoxicity in breast cancer cells
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A series of cinnamylideneacetophenones were synthesized via a modified Claisen-Schmidt condensation reaction and evaluated for cytotoxicity against breast cancer cells using the Alamar Blue assay. Derivatives 17 and 18 bearing a 2-nitro group on the B rin
- Weldon, David J.,Saulsbury, Marilyn D.,Goh, Joshua,Rowland, Leah,Campbell, Petreena,Robinson, Laijia,Miller, Calvin,Christian, Joshua,Amis, Louisa,Taylor, Nia,Dill, Cassandra,Davis Jr., Willie,Evans, Stanley L.,Brantley, Eileen
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p. 3381 - 3384
(2014/07/22)
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- Synthesis of 2,6-diaryl-1,2-dihydropyridines through a 6π-electrocyclization of N-sulfonylazatrienes
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The development of an efficient synthetic method toward substituted 1,2-dihydropyridines from cinnamylideneacetophenones is reported. The key intermediates N-sulfonylazatrienes were synthesized through a TiCl4-mediated direct condensation of primary sulfonamides with the substituted (E,E)-cinnamylideneacetophenones. The 6π-electrocyclization of these intermediates, catalyzed by a Lewis acid, selectively afforded the desired products in good yields.
- Resende, Diana I.S.P.,Guieu, Samuel,Oliva, Cristina G.,Silva, Artur M.S.
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supporting information
p. 6585 - 6588
(2015/01/09)
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- Aldol condensations of a variety of different aldehydes and ketones under ultrasonic irradiation using poly(N-vinylimidazole) as a new heterogeneous base catalyst under solvent-free conditions in a liquid-solid system
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An ultrasound-assisted aldol condensation reaction has been developed for a range of ketones with a variety of aromatic aldehydes using poly(N-vinylimidazole) as a solid base catalyst in a liquid-solid system. The catalyst can be recovered by simple filtration and reused at least 10 times without any significant reduction in its activity. The reaction is also amenable to the large scale, making the procedure potentially useful for industrial applications.
- Khaligh, Nader Ghaffari,Mihankhah, Taraneh
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p. 2167 - 2173
(2014/01/06)
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- NHC-catalyzed annulation of enals to 2,4-dien-1-ones: Efficient diastereoselective synthesis of 1,3-diaryl-4-styrenyl cyclopentenes
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Nucleophilic heterocyclic carbene (NHC)-catalyzed annulation strategy has been utilized for the efficient synthesis of styrenyl-substituted cyclopentenes from 2,4-dienones. Georg Thieme Verlag Stuttgart New York.
- Sinu,Padmaja,Jini,Lakshmi, K.C. Seetha,Nair
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supporting information
p. 1671 - 1674
(2013/09/02)
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- Microwave-assisted convenient synthesis of α,β-unsaturated esters and ketones via aldol-adduct elimination
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Various fluorinated 3-oxo ester/1,3-diketones were reacted with carbonyl compounds, in presence of piperidine and under microwave irradiation, to afford (E)-α,β-unsaturated esters and ketones in good yields. The systematic study reveals that the reaction proceeded through the formation of aldol adduct. The method provides a new and simple way for C,C bond formations. Copyright
- Suman, Pathi,Nageswara Rao, Rayala,China Raju, Bhimapaka
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p. 1548 - 1559
(2013/09/02)
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- Copper-catalyzed asymmetric 1,4-conjugate addition of Grignard reagents to linear α,β,γ,δ-unsaturated ketones
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A highly regioselective and enantioselective copper-catalyzed 1,4-conjugate addition of Grignard reagents to linear α,β,γ,δ- unsaturated ketones was developed. The 1,4-addition products were obtained regioselectively in high yields with up to 98% ee. The Royal Society of Chemistry 2013.
- Ma, Zhenni,Xie, Fang,Yu, Han,Zhang, Yiren,Wu, Xiaoting,Zhang, Wanbin
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supporting information
p. 5292 - 5294
(2013/06/27)
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- Biological and structure-activity evaluation of chalcone derivatives against bacteria and fungi
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The present work describes the antibacterial and antifungal activities of several chalcones obtained by a straight Claisen-Schmidt aldol condensation determined by the minimal inhibitory concentration against different microorganisms (Gram-positive and Gram-negative bacteria and fungi). Solid state crystal structures of seven chalcones were determined by X-ray diffraction (XRD) analysis. Chemometric studies were carried out in order to identify a potential structureactivity relationship.
- Silva, Wender A.,Andrade, Carlos Kleber Z.,Napolitano, Hamilton B.,Vencato, Ivo,Lariucci, Carlito,De Castro, Miria M. R. C.,Camargo, Ademir J.
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p. 133 - 144
(2013/04/24)
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- Effects of structural and electronic characteristics of chalcones on the activation of peroxisome proliferator-activated receptor gamma
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Chalcones share some structural similarities with GW-1929, a highly-selective and potent agonist for peroxisome proliferator-activated receptor-gamma (PPARγ). In this study, we tested 53 structurally diverse chalcones to identify characteristics essential for PPARγ activation in a GAL4-based transactivation assay. This screen identified several novel chalcone agonists of PPARγ. Our results indicate that chalcones with an electron rich group or sterically large groups such as naphthyl on the carbonyl side tend to activate PPARγ. The absence of any strict structural or electronic requirements suggests that the flexibility of the PPARγ ligand binding pocket may allow binding of diverse chalcones with some preference for a slightly larger electron-rich group on the carbonyl side. We predict that further structure-activity relationship studies on chalcones with naphthalene or electron-rich groups near the carbonyl moiety will lead to the development of more potent PPARγ agonists.
- Schott, Jason Taylor,Mordaunt, Charles Edward,Vargas, Anthony Joseph,Leon, Martin Antonio,Chen, Kevin Hsinwen,Singh, Mandeep,Satoh, Mikiko,Cardenas, Emilio Leal,Maitra, Santanu,Patel, Nilay Vinod,De Lijser, Hubrecht Johan Peter
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p. 229 - 236
(2013/03/14)
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- Synthesis of substituted fluorenes by cascade allenylation, electrocyclization and intramolecular friedel-crafts reaction of 1,3-diene-substituted propargylic alcohols
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A concise, one-step synthesis of substituted fluorenes through TiCl 4-promoted cascade allenylation, electrocyclization and intramolecular Friedel-Crafts reaction of 1,3-diene-substituted propargylic alcohols has been developed. An interesting substituent-dependent regioselectivity was observed.
- Xu, Xiangsheng,Li, Tao,Li, Xiaoqing,Shao, Jiangbin
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p. 383 - 388
(2013/04/23)
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- Two expedient 'one-pot' methods for synthesis of β-aryl-β- mercaptoketones over anhydrous potassium carbonate or amberlyst-15 catalyst
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Two expedient one-pot methods have been developed for synthesis of β-aryl-β-mercaptoketones using acetophenones, benzaldehydes and thiols as starting materials. The methods involve microwave irradiation (5min) of 1:1 mixtures of acetophenones and benzaldehydes over neutral alumina supported anhydrous potassium carbonate or amberlyst-15 in the first step, and that is followed by addition of thiol to the resulting material and keeping at room temperature for 1.5 h. Indian Academy of Sciences.
- Guha, Chayan,Mondal, Rina,Pal, Rammohan,Mallik, Asok K.
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p. 1463 - 1470
(2014/04/03)
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- Synthesis, structure, growth and characterization of an organic crystal: 1,5-diphenylpenta-2,4-dien-1-one
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1,5-Diphenylpenta-2,4-dien-1-one (DDO) chalcone single crystals, synthesized by a base-catalysed aldol condensation reaction between cinnamaldehyde and acetophenone, have been grown by the slow evaporation of an ethanol solution. The crystals belong to the orthorhombic system with centrosymmetric space group Pbca. The DDO crystals are transparent in the visible region and have a lower optical cut-off at ~445 nm with a band-gap energy of 2.87 eV. Thermogravimetry/differential scanning calorimetry thermal analysis shows that the crystal is stable up to 375 K and it has a good chemical stability. The vibrational patterns of the chalcone have been investigated by Fourier transform IR and Fourier transform Raman spectroscopy. Microhardness studies were also carried out to elucidate the mechanical behaviour. Theoretical calculations were performed using the Hartree-Fock method with 6-31G(d,p) as the basis set, and the first-order hyperpolarizability is 7.077 × 10 -30 electrostatic units, which is >25 times that of urea. The crystalline perfection evaluated by high-resolution X-ray diffraction analysis reveals multiple peaks. The molecular packing leads to a centrosymmetric arrangement, resulting in zero second harmonic generation [χ(2) = 0] efficiency. Interestingly, the bromo- and chloro-substituted chalcones are good nonlinear optical materials.
- Rajasekar,Muthu,Bhagavannarayana,Meenakshisundaram
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p. 914 - 920
(2012/10/29)
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- Lithium amidoborane, a highly chemoselective reagent for the reduction of α,β-unsaturated ketones to allylic alcohols
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Lithium amidoborane (LiNH2BH3, LiAB for short), is capable of chemoselectively reducing α,β-unsaturated ketones to the corresponding allylic alcohols at ambient temperature. A mechanistic study shows that the reduction is via a double hydrogen transfer process. The protic H(N) and hydridic H(B) in amidoborane add to the O and C sites of the carbonyl group, respectively.
- Xu, Weiliang,Zhou, Yonggui,Wang, Ruimin,Wu, Guotao,Chen, Ping
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supporting information; experimental part
p. 367 - 371
(2012/01/13)
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- Iodine-catalysed conjugate addition of indole with α- cinnamylideneketones: Formation of β-(3-indolyl)-α,β-dihydro- α-cinnamylideneketones and bis(3-indolyl)methylbenzene
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β-(3-Indolyl)-α,β-dihydro-α-cinnamylideneketones and bis(3-indolyl)methylbenzene have been obtained in moderate to good yield by conjugate addition of indole with α-cinnamylideneketones under mild reaction condition in dry ethanol using iodine as catalyst. The structures of the products have been established from their spectral data.
- Pal, Rammohan,Mandal, Tapas K.,Mallik, Asok K.
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experimental part
p. 619 - 623
(2011/06/21)
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- Amberlyst-15 catalysed microwave assisted cross-aldol condensation between ketones and aldehydes under solvent free condition
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Amberlyst-15 has been applied as an efficient heterogeneous catalyst for the first time for rapid synthesis of α,α′-bis(arylmethylene) cycloalkanones, α,α′-bis(cinnamylidene)cycloalkanones, ′-cinnamylideneacetophenones and chalcones in very good yield by the reaction between various aldehydes and ketones under microwave irradiation. The new process for the cross-aldol condensation reaction works well in absence of any solvent. The yields are high and the process is environmentally benign.
- Pal, Rammohan,Mandal, Tapas K.,Guha, Chayan,Mallik, Asok K.
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experimental part
p. 711 - 717
(2012/03/11)
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- Design, synthesis, and bioactivities screening of a diaryl ketone-inspired pesticide molecular library as derived from natural products
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Three natural products, 1,5-diphenylpentan-1-one, 1,5-diphenylpent-2-en-1-one, and 3-hydroxy-1,5-diphenylpentan-1-one, with good insecticidal activities were extracted from Stellera chamaejasme L. Based on their shared diaryl ketone moiety as 'pharmacophores', a series of diaryl ketones were synthesized and tested for insecticidal activity, acetylcholinesterase inhibitory activity, and antifungal activity. All synthesized compounds showed poor insecticidal and acetylcholinesterase inhibitory activities. Compound III with a furyl ring showed strong activities against plant pathogenic fungi. The IC50 of compound (E)-1-(2,4-dichlorophenyl)-3-(furan-2-yl)- -prop-2-en-1-one (III2) was 1.20mg/L against Rhizoctonia solani, suggesting its strong potential as a novel antifungal drug.
- Zhang, Hong,Jin, Hong,Ji, Lan-Zhu,Tao, Ke,Liu, Wei,Zhao, Hao-Yu,Hou, Tai-Ping
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experimental part
p. 94 - 100
(2012/06/01)
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- Mosquito larvicidal studies of some chalcone analogues and their derived products: Structure-activity relationship analysis
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A series of chalcone analogues and some of their derivatives were synthesized and subjected to the mosquito larvicidal study. Chalcones having electron releasing group(s) on either ring A or ring B showed high toxicity. Electron withdrawing group(s), especially at ring B, reduced the activity of chalcones. The activity was abruptly decreased due to replacement of ring A by CH3, extension of conjugation or blocking of α,β- unsaturated ketone part of chalcones by derivatization. Quantitative structure-activity relationship (QSAR) studies of these compounds were performed using various spatial, electronic and physicochemical parameters. Genetic Function approximation with linear and spline options was used as the chemometric tool for developing the QSAR models.
- Begum, Naznin A.,Roy, Nayan,Laskar, Rajibul A.,Roy, Kunal
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experimental part
p. 184 - 191
(2012/02/16)
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