- UV-Light-Induced Dehydrogenative N -Acylation of Amines with 2-Nitrobenzaldehydes to Give 2-Aminobenzamides
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A simple, mild, green, and efficient method for the synthesis of 2-aminobenzamides is highly desirable. Herein, we report the development of an efficient, one-pot strategy starting from 2-aminobenzaldehydes and amines with acetic acid in ethyl acetate/acetone using irradiation with UV light for the synthesis of 2-aminobenzamides in high yields; 32 examples proceeded successfully by this photo-induced protocol in up to 92% yield. The reaction was also readily achieved on a gram scale. The utility of the 2-aminobenzamide building block in organic synthesis was shown by their use in the preparation of quinazolinone derivatives. The method was applied to amino acid derivatives as the amine component, which smoothly gave N-(2-aminobenzoyl)acetate derivatives at room temperature. Finally, a plausible mechanism is proposed.
- Deng, Wei,Kambe, Nobuaki,Qiu, Renhua,Tang, Niu,Xiang, Jiannan,Yang, Tianbao,Yin, Shuang-Feng,Zeng, Dishu
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supporting information
(2022/03/17)
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- N,N-Dimethylformamide as Carbon Synthons for the Synthesis ofN-Heterocycles: Pyrrolo/Indolo[1,2-a]quinoxalines and Quinazolin-4-ones
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N,N-dimethylformamide (DMF) as synthetic precursors contributing especially the methyl, acyl, and amino groups has played a significant role in heterocycle syntheses and functionalization. In this protocol, a wide range of pyrrolo/indolo[1,2-a]quinoxalines and quinazolin-4-ones were obtained in moderate to good yields by using elemental iodine without any metal or peroxides. We considered thatN-methyl andN-acyl of DMF participate and complete the reaction separately through different mechanisms, which displayed potential still to be explored of DMF.
- Ding, Chengcheng,Li, Shichen,Ma, Chen,Ren, Jianing,Wang, Yishou
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p. 16848 - 16857
(2021/12/06)
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- Design, synthesis, in vitro and in silico biological assays of new quinazolinone-2-thio-metronidazole derivatives
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A new series of quinazolinone-2-thio-metronidazole derivatives 9a-o was designed, synthesized and assayed for their activities against metabolic enzymes human carbonic anhydrase I and II (hCAs I and II), acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α-glucosidase. The results indicated that all the synthesized compounds exhibited excellent inhibitory activities against mentioned enzymes as compared with standard inhibitors. Representatively, the most potent compound against CA enzymes, 4-fluorophenyl derivative 9i, was 4 and 7-times more potent than standard inhibitor acetazolamide against hCA I and II, respectively; 4-fluorobenzyl derivative 9m as the most potent compound against cholinesterase enzymes, was around 11 and 21-times more potent than standard inhibitor tacrine against AChE and BChE, respectively; the most active α-glucosidase inhibitor 9h with 4-methoxyphenyl moiety was 5-times more active that acarbose as standard inhibitor. Furthermore, in order to study interaction modes of the most potent compounds in the active site of their related enzymes, molecular modeling was performed. Druglikeness, ADME, and toxicity profile of the compounds 9i, 9m, and 9h were also predicted.
- Ansari, Samira,Asgari, Mohammad Sadegh,Biglar, Mahmood,Esfahani, Ensieh Nasli,Hamedifar, Haleh,Larijani, Bagher,Mahdavi, Mohammad,Mohammadi-Khanaposhtani, Maryam,Rastegar, Hossein,Tas, Recep,Taslimi, Parham
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- Green synthesis of novel phosphonate derivatives using ultrasonic irradiation
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[Figure not available: see fulltext.] A novel and efficient procedure for the generation of quinazolinone phosphonate derivatives employing the reaction of euparin, isatin or its derivatives, primary amines, dialkyl acetylenedicarboxylates, trimethyl phosphite or triphenyl phosphite, and acidic solution of hydrogen peroxide in aqueous media at ambient temperature under ultrasonic irradiation was developed. Without ultrasonic irradiation, the reaction does not proceed and agitation of the reaction mixture is difficult. Some advantages of this procedure are: short time of reaction, high yields of products, easy isolation of products.
- Sharafian, Shirin,Hossaini, Zinatossadat,Rostami-Charati, Faramarz,Khalilzadeh, Mohammad A.
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p. 1283 - 1291
(2020/11/19)
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- Design and synthesis of diphenylpyrimidine derivatives (DPPYs) as potential dual EGFR T790M and FAK inhibitors against a diverse range of cancer cell lines
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A new class of pyrimidine derivatives were designed and synthesized as potential dual FAK and EGFRT790M inhibitors using a fragment-based drug design strategy. This effort led to the identification of the two most active inhibitors, namely 9a and 9f, against both FAK (IC50 = 1.03 and 3.05 nM, respectively) and EGFRT790M (IC50 = 3.89 and 7.13 nM, respectively) kinase activity. Moreover, most of these compounds also exhibited strong antiproliferative activity against the three evaluated FAK-overexpressing pancreatic cancer (PC) cells (AsPC-1, BxPC-3, Panc-1) and two drug-resistant cancer cell lines (breast cancer MCF-7/adr cells and lung cancer H1975 cells) at concentrations lower than 6.936 μM. In addition, 9a was also effective in the in vivo assessment conducted in a FAK-driven human AsPC-1 cell xenograft mouse model. Overall, this study offers a new insight into the treatment of hard to treat cancers.
- Ai, Min,Wang, Changyuan,Tang, Zeyao,Liu, Kexin,Sun, Xiuli,Ma, Tengyue,Li, Yanxia,Ma, Xiaodong,Li, Lei,Chen, Lixue
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- Synthesis of 2-aryl quinazolinones: Via iron-catalyzed cross-dehydrogenative coupling (CDC) between N-H and C-H bonds
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Herein, we describe the direct synthesis of quinazolinones via cross-dehydrogenative coupling between methyl arenes and anthranilamides. The C-H functionalization of the benzylic sp3 carbon is achieved by di-t-butyl peroxide under air, and the subsequent amination-aerobic oxidation process completes the annulation process. Iron catalyzed the whole reaction process and various kinds of functional groups were tolerated under the reaction conditions, providing 31 examples of 2-aryl quinazolinones using methyl arene derivatives in yields of 57-95percent. The synthetic potential has been demonstrated by the additional synthesis of aryl-containing heterocycles. This journal is
- Jang, Yoonkyung,Lee, Seok Beom,Hong, Junhwa,Chun, Simin,Lee, Jeeyeon,Hong, Suckchang
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supporting information
p. 5435 - 5441
(2020/08/03)
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- A novel approach for the synthesis of functionalized hydroxylamino derivative of dihydroquinazolinones
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A new metal-free and modular approach for the synthesis of various functionalized dihydroquinazolinones has been developed from isatoic anhydride, amines, 4-chloro-N-hydroxybenzimidoylchloride to yield up to 71%. The reaction has been screened in various bases, solvents at different temperatures. The substrate scope of the reaction has been studied with various amines and the possible reaction mechanism for this reaction has also been proposed.
- Jaganmohan, Chikkanti,Vinay Kumar,Venkateshwarlu,Mohanty, Sandeep,Kumar, Jaydeep,Venkateswara Rao,Raghunadh, Akula,Tadiparthi, Krishnaji
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supporting information
p. 2163 - 2170
(2020/06/10)
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- Novel quinazolin–sulfonamid derivatives: synthesis, characterization, biological evaluation, and molecular docking studies
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In the design of novel drugs, the formation of hybrid molecules via the combination of several pharmacophores can give rise to compounds with interesting biochemical profiles. A series of novel quinazolin–sulfonamid derivatives (9a–m) were synthesized, characterized and evaluated for their in vitro antidiabetic, anticholinergics, and antiepileptic activity. These synthesized novel quinazolin–sulfonamid derivatives (9a–m) were found to be effective inhibitor molecules for the α-glycosidase, human carbonic anhydrase I and II (hCA I and hCA II), butyrylcholinesterase (BChE) and acetylcholinesterase (AChE) enzyme, with Ki values in the range of 100.62 ± 13.68–327.94 ± 58.21 nM for α-glycosidase, 1.03 ± 0.11–14.87 ± 2.63 nM for hCA I, 1.83 ± 0.24–15.86 ± 2.57 nM for hCA II, 30.12 ± 3.81–102.16 ± 13.87 nM for BChE, and 26.16 ± 3.63–88.52 ± 20.11 nM for AChE, respectively. In the last step, molecular docking calculations were made to compare biological activities of molecules against enzymes which are achethylcholinesterase, butyrylcholinesterase and α-glycosidase. Communicated by Ramaswamy H. Sarma.
- Sepehri, Nima,Mohammadi-Khanaposhtani, Maryam,Asemanipoor, Nafise,Hosseini, Samanesadat,Biglar, Mahmood,Larijani, Bagher,Mahdavi, Mohammad,Hamedifar, Haleh,Taslimi, Parham,Sadeghian, Nastaran,Norizadehtazehkand, Mostafa,Gulcin, Ilhami
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- Method for preparing 2-amino-3,5-dichloro-N-isopropylbenzamide
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The invention discloses a method for preparing 2-amino-3,5-dichloro-N-isopropylbenzamide. The method comprises the following steps: (1) preparation of mixed amide: adding isatoic anhydride to a reaction solvent with the reaction concentration, which is a ratio of the solvent volume to the weight of isatoic anhydride, of 5-10 times and the reaction temperature at 20-40 DEG C, adding isopropylaminedropwise, monitoring the reaction progress in the liquid phase, and performing a reaction of a next step directly without separation after completion of the monitored reaction; and (2), preparation of2-amino-3,5-dichloro-N-isopropylbenzamide: adding dichlorohydantoin slowly to the reaction solution of the step (1), controlling the reaction temperature at 20-40 DEG C, monitoring the reaction progress in the liquid phase, performing vacuum concentration on the reaction system after completion of the reaction, performing suction filtration, washing the solid with a little hot water, and performing beating with methanol so as to obtain a white compound. According to the method for preparing 2-amino-3,5-dichloro-N-isopropylbenzamide, a novel chlorination method is adopted so as to obtain 2-amino-3,5-dichloro-N-isopropylbenzamide efficiently, and the preparation method has simple post-treatment and a high total yield.
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Paragraph 0011
(2019/08/20)
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- Design, synthesis and insecticidal activity of diamides with oxydibenzene or diphenylamine subunits
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Introduction: After using insecticides over many years, the resistance and environmental issues have become great challenges to crop protection. Modern agriculture calls for new insecticidal candidates. Phthalic diamide insecticide containing adjacent two amide group were favored for its new mode of action. Most chemical optimizations of phthalic diamide insecticide focused on amide groups. Modifications on phenyl part including fewer substituent types. Objective: The objective of this article was to investigate the insecticidal activities variation by alter the orientation and distance of two amide by replace the phenyl part with oxydibenzene and diphenyl-amine. Results: The target compounds were synthesized by using Cu/CuI catalyzed Ullmann coupling and sulfonyl-O-acryl mixed-anhydride as reactive intermediate. All target compounds were evaluated against armyworm (Mythimna sepatara). Two of synthetic compounds containing multifluoro-alkoxyl substituent showed mortality rate of 100% at 500 mg L-1. DFT-based Potential energy surface scanning showed that the relative energies of three conformations of insecticidal compounds were very similar Conclusion: We designed, synthesized and characterized seventeen novel compounds for the insecticidal candidates. Two of them were found to be insecticidal. A preliminary structure-activity relationship showed that the multifluoro-alkoxyl groups on the benzene were preferred. The compound d5 could be a lead compound for further research.
- Liu, Ye,Chen, Xinfei,Xu, Xiaoyong,Cheng, Jiagao,Shao, Xusheng,Li, Zhong
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p. 262 - 269
(2017/02/15)
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- 3,5-dihalogenated thiophosphoro benzamides insecticide
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The invention discloses a 3,5-dihalogenation sulfo-benzamide insecticide and preparation method and application thereof. The 3,5-dihalogenation sulfo-benzamide insecticide is represented as a structural formula I. In the formula I: R1 is C1 or Br, R2 is selected from methyl, isopropyl and allyl, and R3 is H or C1. The 3,5-dihalogenation sulfo-benzamide insecticide can be used for prevention and control of agricultural insects or forest insects.
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Paragraph 0038; 0039; 0040; 0041
(2017/04/22)
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- An efficient four-step approach toward fused triazino[1,6-a] quinazolines
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Herein, we describe a simple, four-step process for the preparation of 1,2,3-triazino[1,6-a]quinazolin-13-ones. This method involves ring-opening, quinazoline-forming condensation, reduction, diazotization accompanied by rapid intramolecular cyclization in the last step afforded the desired products with structurally complex heterocyclic core in excellent to high yields.
- Sayahi, Mohammad Hosein,Baghersaei, Shirin,Goli, Fereshteh,Moghimi, Setareh,Mahdavi, Mohammad,Firoozpour, Loghman,Shafiee, Abbas,Foroumadi, Alireza
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p. 189 - 192
(2016/05/09)
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- CuBr/Et3N-Promoted Reactions of 2-Aminobenzamides and Isothiocyanates: Efficient Synthesis of Novel Quinazolin-4(3H)-ones
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A series of novel quinazolin-4(3H)-one derivatives were efficiently synthesized starting from isatoic anhydride. First, reaction of isatoic anhydride and amines in H2O at room temperature afforded 2-aminobenzamides. Then, CuBr/Et3N promoted reaction of 2-aminobenzamides and different aryl isothiocyanates in DMF at 80° afforded the title compounds in good yield.
- Mahdavi, Mohammad,Asadi, Mehdi,Khoshbakht, Mahsa,Saeedi, Mina,Bayat, Mohammad,Foroumadi, Alireza,Shafiee, Abbas
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p. 378 - 383
(2016/06/01)
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- Diversified facile synthesis of benzimidazoles, quinazolin-4(3H)-ones and 1,4-benzodiazepine-2,5-diones via palladium-catalyzed transfer hydrogenation/condensation cascade of nitro arenes under microwave irradiation
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A highly efficient diversified methodology for preparation of benzimidazole, quinazolin-4(3H)-ones and 1,4-benzodiazepine-2,5-diones is established using a palladium-catalyzed transfer hydrogenation (CTH)/condensation cascade of o-nitroaniline and o-nitrobenzamides in a triethylamine-formic acid azeotropic mixture (2:5) under microwave irradiation.
- Zhu, Kaicheng,Hao, Jian-Hong,Zhang, Cheng-Pan,Zhang, Jiajun,Feng, Yiqing,Qin, Hua-Li
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p. 11132 - 11135
(2015/03/05)
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- Synthesis and anticancer activity of N -substituted 2-arylquinazolinones bearing trans -stilbene scaffold
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A novel series of 2-arylquinazolinones 7a-o bearing trans-stilbene moiety were designed, synthesized, and evaluated against human breast cancer cell lines including human breast adenocarcinoma (MCF-7 and MDA-MB-231) and human ductal breast epithelial tumor (T-47D). Among the tested compounds, the sec-butyl derivative 7h showed the best profile of activity (IC50 5 μM) against all cell lines, being 2-fold more potent than standard drug, etoposide. Our investigation revealed that the cytotoxic activity was significantly affected by N3-alkyl substituents. Furthermore, the morphological analysis by acridine orange/ethidium bromide double staining test and flow cytometry analysis indicated that the prototype compound 7h can induce apoptosis in MCF-7 and MDA-MB-231 cells.
- Mahdavi, Mohammad,Pedrood, Keyvan,Safavi, Maliheh,Saeedi, Mina,Pordeli, Mahboobeh,Ardestani, Sussan Kabudanian,Emami, Saeed,Adib, Mehdi,Foroumadi, Alireza,Shafiee, Abbas
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p. 492 - 499
(2015/04/14)
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- Copper-catalyzed radical methylation/C-H amination/oxidation cascade for the synthesis of quinazolinones
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A copper-catalyzed radical methylation/sp3 C-H amination/oxidation reaction for the facile synthesis of quinazolinone was developed. In this cascade reaction, dicumyl peroxide acts not only as a useful oxidant but also as an efficient methyl source. Notably, a methyl radical, generated from peroxide, was confirmed by electron paramagnetic resonance for the first time.
- Bao, Yajie,Yan, Yizhe,Xu, Kun,Su, Jihu,Zha, Zhenggen,Wang, Zhiyong
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p. 4736 - 4742
(2015/05/13)
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- I2-catalyzed aerobic oxidative C(sp3)-H amination/C-N cleavage of tertiary amine: Synthesis of quinazolines and quinazolinones
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An iodine-catalyzed oxidative C(sp3)-H amination/C-N cleavage of tertiary amines couducted under an oxygen atmosphere has been developed and affords a route to quinazolines and quinazolinones in good to excellent yields via a domino ring annulation. The method is metal-free, peroxide-free, and operationally simple to implement with a wide scope of substrates and represents a new avenue for multiple C-N bond formations.
- Yan, Yizhe,Xu, Ying,Niu, Bin,Xie, Huifang,Liu, Yanqi
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p. 5581 - 5587
(2015/06/16)
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- Novel 1,2,3,4-Tetrahydroquinazolinones via Reaction of 2-Amino-N-substituted Benzamides and Dimethyl Acetylenedicarboxylate
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Reaction of 2-amino-N-substituted benzamides and dimethyl acetylenedicarboxylate (DMAD) in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in H2O at room temperature led to the formation of novel 1,2,3,4-tetrahydroquinazolinones.
- Nahavandian, Semiramis,Allameh, Sadegh,Saeedi, Mina,Ansari, Shirin,Mahdavi, Mohammad,Foroumadi, Alireza,Shafiee, Abbas
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p. 1028 - 1033
(2015/11/23)
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- Convenient and sequential one-pot route for synthesis of 2-thioxoquinazolinone and quinazolinobenzothiazinedione derivatives
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A new and efficient synthetic process has been developed for preparation of 2-thioxoquinazolinone and quinazolinobenzothiazinedione derivatives. The related products were synthesized through reaction of isatoic anhydride, amines/anthranilic acids, and carbon disulfide (CS2) in the presence of potassium hydroxide in ethanol at reflux. Graphical abstract: [Figure not available: see fulltext.]
- Asadi, Mehdi,Masoomi, Shiva,Ebrahimi, Seyed Mostafa,Mahdavi, Mohammad,Saeedi, Mina,Shafiee, Abbas,Foroumadi, Alireza
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p. 497 - 504
(2014/03/21)
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- Vilsmeier Reagent: An efficient reagent for the transformation of 2-aminobenzamides into quinazolin-4(3 h)-one derivatives
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Clean and easy preparation of quinazolin-4(3H)-one derivatives using 2-aminobenzamides and Vilsmeier reagent is described. 2-Aminobenzamides were converted into the corresponding quinazolinones under mild and efficient conditions, in good yields without undesirable by-products.
- Farzipour, Soghra,Saeedi, Mina,Mahdavi, Mohammad,Yavari, Hossein,Mirzahekmati, Mohammadreza,Ghaemi, Nasser,Foroumadi, Alireza,Shafiee, Abbas
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p. 481 - 487
(2014/01/23)
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- One-pot synthesis of 2-amino-4(3H)-quinazolinones via ring-opening of isatoic anhydride and palladium-catalyzed oxidative isocyanide-insertion
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An efficient and practical two-step process has been developed for the synthesis of 2-amino-4(3H)-quinazolinones via ring-opening of isatoic anhydride and palladium-catalyzed oxidative isocyanide-insertion in one pot. This regioselective procedure could construct a wide range of 2-amino-4(3H)- quinazolinones in moderate to excellent yields. Furthermore, the methodology also had distinct advantages of easily accessible starting materials and operational simplicity. the Partner Organisations 2014.
- Ji, Fei,Lv, Mei-Fang,Yi, Wen-Bin,Cai, Chun
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p. 5766 - 5772
(2014/07/22)
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- Structural optimization of a retrograde trafficking inhibitor that protects cells from infections by human polyoma- and papillomaviruses
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Human polyoma- and papillomaviruses are non-enveloped DNA viruses that cause severe pathologies and mortalities. Under circumstances of immunosuppression, JC polyomavirus causes a fatal demyelinating disease called progressive multifocal leukoencephalopathy (PML) and the BK polyomavirus is the etiological agent of polyomavirus-induced nephropathy and hemorrhagic cystitis. Human papillomavirus type 16, another non-enveloped DNA virus, is associated with the development of cancers in tissues like the uterine cervix and oropharynx. Currently, there are no approved drugs or vaccines to treat or prevent polyomavirus infections. We recently discovered that the small molecule Retro-2cycl, an inhibitor of host retrograde trafficking, blocked infection by several human and monkey polyomaviruses. Here, we report diversity-oriented syntheses of Retro-2cycl and evaluation of the resulting analogs using an assay of human cell infections by JC polyomavirus. We defined structure-activity relationships and also discovered analogs with significantly improved potency as suppressors of human polyoma- and papillomavirus infection in vitro. Our findings represent an advance in the development of drug candidates that can broadly protect humans from non-enveloped DNA viruses and toxins that exploit retrograde trafficking as a means for cell entry.
- Carney, Daniel W.,Nelson, Christian D.S.,Ferris, Bennett D.,Stevens, Julia P.,Lipovsky, Alex,Kazakov, Teymur,Dimaio, Daniel,Atwood, Walter J.,Sello, Jason K.
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p. 4836 - 4847
(2014/10/16)
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- Development of novel 2-[4-(aminoalkoxy)phenyl]-4(3H)-quinazolinone derivatives as potent and selective histamine H3 receptor inverse agonists
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Novel 2-[4-(aminoalkoxy)phenyl]-4(3H)-quinazolinone derivatives were identified as potent human H3 receptor inverse agonists. After systematic modification of lead 5a, the potent and selective analog 5r was identified. Elimination of hERG K+ channel and human α1A-adrenoceptor activities is the main focus of the present study.
- Mizutani, Takashi,Nagase, Tsuyoshi,Ito, Sayaka,Miyamoto, Yasuhisa,Tanaka, Takeshi,Takenaga, Norihiro,Tokita, Shigeru,Sato, Nagaaki
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scheme or table
p. 6041 - 6045
(2009/06/30)
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- ANTHRANILAMIDES
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The present invention relates to a compound of Formula I: or a pharmaceutically acceptable salt thereof wherein R1, R2, and Het are as defined herein. Compounds of the present invention are useful as Aurora kinase inhibitors.
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Page/Page column 15-16
(2009/01/20)
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- ANTHRANILAMIDE INHIBITORS OF AURORA KINASE
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The present invention relates to a compound represented by the following formula: or a pharmaceutically acceptable salt thereof; where R1, R2, R3, R4, r and s are as previously defined. Compounds of the present invention are useful in the treatment of diseases associated with Aurora kinase activity such as cancer.
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Page/Page column 9-10
(2008/12/07)
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- Insecticidal anthranilic diamides: A new class of potent ryanodine receptor activators
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A novel class of anthranilic diamides has been discovered with exceptional insecticidal activity on a range of Lepidoptera. These compounds have been found to exhibit their action by release of intracellular Ca2+ stores mediated by the ryanodine receptor. The discovery, synthesis, structure-activity, and biological results are presented.
- Lahm, George P.,Selby, Thomas P.,Freudenberger, John H.,Stevenson, Thomas M.,Myers, Brian J.,Seburyamo, Gilles,Smith, Ben K.,Flexner, Lindsey,Clark, Christopher E.,Cordova, Daniel
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p. 4898 - 4906
(2007/10/03)
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- Imidazoline derivatives as alpha-1A adrenoceptor ligands
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Compound of formula (I) or a pharmaceutically acceptable salt or solvate thereof are disclosed. Such compounds are useful in the treatment of Alpha-1A mediated diseases or conditions such as urinary incontinence.
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Page/Page column 18
(2010/02/11)
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- Preparation of anthranilamides
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A process for the preparation of an anthranilamide of the formula STR1 in which R1 and R2 each independently is hydrogen or C1 to C4 alkyl, or R1 and R2, together with the nitrogen atom to which they are bonded, form a heterocyclic ring, comprising reacting isatoic anhydride of the formula STR2 with an approximately equimolar amount of an amine of the formula STR3 in water at a pH of about 7 to 10.5 and a temperature of about 20° to 100° C. Advantageously the reaction is effected in the presence of a buffer system comprising an amine of the formula STR4 plus at least one of a hydrohalide and carbonic acid salt of such amine, e.g. ammonia or a lower alkyl amine plus the corresponding hydrochloride and/or carbonate.
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