- ADME properties, bioactivity and molecular docking studies of 4-amino-chalcone derivatives: new analogues for the treatment of Alzheimer, glaucoma and epileptic diseases
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In this study, in vitro inhibition effects of (E)-1-(4-aminophenyl)-3-(aryl) prop-2-en-1-one (4-amino-chalcones) derivatives (3a–o) on acetylcholinesterase (AChE) enzyme and human erythrocyte carbonic anhydrase I and II isoenzymes (hCA I- II) were investigated. And also, the biological activities of 4-amino-chalcone derivatives against enzymes which names are acetylcholinesterase (PDB ID: 1OCE), human Carbonic Anhydrase I (PDB ID: 2CAB), human carbonic anhydrase II (PDB ID: 3DC3), were compared. After the results obtained, ADME/T analysis was performed in order to use 4-amino-chalcone derivatives as a drug in the future. Effective inhibitors of carbonic anhydrase I and II isozymes (hCAI and II) and acetylcholinesterase (AChE) enzymes with Ki values in the range of 2.55 ± 0.35–11.75 ± 3.57?nM for hCA I, 4.31 ± 0.78–17.55 ± 5.86?nM for hCA II and 96.01 ± 25.34–1411.41 ± 32.88?nM for AChE, respectively, were the 4-amino-chalcone derivatives (3a–o) molecules.
- Gürdere, Meliha Burcu,Budak, Yakup,Kocyigit, Umit M.,Taslimi, Parham,Tüzün, Burak,Ceylan, Mustafa
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- Design, synthesis and antibacterial activity of chalcones against MSSA and MRSA planktonic cells and biofilms
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Staphylococcus aureus is the one of the most successful modern pathogens. The same bacterium that lives as a skin and mucosal commensal can be transmitted in health-care and community-settings and causes severe infections. Thus, there is a great challenge for a discovery of novel anti-Staphylococcus aureus compounds, which should act against resistant strains. Herein, we designed and synthesized a series of 17 chalcones, substituted by amino group on ring A, which were evaluated against methicillin-susceptible S. aureus (MSSA) and methicillin-resistant S. aureus MRSA planktonic cells. The antibacterial potency was improved by substituents on ring B, which were designed according to Topliss’ manual method. 4-bromo-3′-aminochalcone (5f) was the most active, demonstrating minimum inhibitory concentration (MIC) values of 1.9 μg mL?1 and 7.8 μg mL?1 against MSSA and MRSA, respectively. The association of 5f with vancomycin demonstrated synergistic effect against MSSA and MRSA, with Fractional Inhibitory Concentration Index (FICI) values of 0.4 and 0.3, respectively. Subinhibitory concentration of 5f inhibited the MSSA and MRSA adhesion to human keratinocytes. Chalcone 5f was able to reduce MSSA and MRSA biofilm formation, as well as acts on preformed biofilm in concentration-dependent mode. Scanning electron microscopy analyses confirmed severe perturbations caused by 5f on MSSA and MRSA biofilm architecture. The acute toxicity assay, using Galleria mellonella larvae, indicated a low toxic effect of 5f after 72 h, displaying lethality of 20% and 30% at 7.8 μg mL?1 and 78.0 μg mL?1, respectively. In addition, the antibacterial activity spectrum of 5f indicated action against planktonic cells of Enterococcus faecalis (MIC = 7.8 μg mL?1), Acinetobacter baumannii (MIC = 15.6 μg mL?1) and Mycobacterium tuberculosis (MIC = 5.7 μg mL?1). Altogether, these results open new avenues for 5f as an anti-Staphylococcus aureus agent, with potential applications as antibacterial drug, adjunct of antibiotics and medical devices coating.
- Garcia, Mayara A.R.,Theodoro, Reinaldo S.,Sardi, Janaina C.O.,Santos, Mariana B.,Ayusso, Gabriela M.,Pavan, Fernando R.,Costa, Alan R.,Santa Cruz, Lucas M.,Rosalen, Pedro L.,Regasini, Luis O.
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- Design, synthesis, and anticancer activity studies of novel quinoline-chalcone derivatives
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The chalcone and quinoline scaffolds are frequently utilized to design novel anticancer agents. As the continuation of our work on effective anticancer agents, we assumed that linking chalcone fragment to the quinoline scaffold through the principle of molecular hybridization strategy could produce novel compounds with potential anticancer activity. Therefore, quinoline-chalcone derivatives were designed and synthesized, and we explored their antiproliferative activity against MGC-803, HCT-116, and MCF-7 cells. Among these compounds, compound 12e exhibited a most excellent inhibitory potency against MGC-803, HCT-116, and MCF-7 cells with IC50 values of 1.38, 5.34, and 5.21 μM, respectively. The structure–activity relationship of quinoline-chalcone derivatives was preliminarily explored in this report. Further mechanism studies suggested that compound 12e inhibited MGC-803 cells in a dose-dependent manner and the cell colony formation activity of MGC-803 cells, arrested MGC-803 cells at the G2/M phase and significantly upregulated the levels of apoptosis-related proteins (Caspase3/9 and cleaved-PARP) in MGC-803 cells. In addition, compound 12e could significantly induce ROS generation, and was dependent on ROS production to exert inhibitory effects on gastric cancer cells. Taken together, all the results suggested that directly linking chalcone fragment to the quinoline scaffold could produce novel anticancer molecules, and compound 12e might be a valuable lead compound for the development of anticancer agents.
- Guan, Yong-Feng,Li, Wen,Li, Yin-Ru,Liu, Wen-Bo,Liu, Xiu-Juan,Song, Jian,Tian, Xin-Yi,Yu, Guang-Xi,Yuan, Xin-Ying,Zhang, Sai-Yang,Zhang, Yan-Bing
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- Synthesis, Antiproliferative and Cytotoxic Activities, DNA Binding Features and Molecular Docking Study of Novel Enamine Derivatives
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Novel enamine derivatives were synthesized from the reaction of lactone and chalcones and their antiproliferative and cytotoxic activities against six cancer cell lines (e. g., HeLa, HT29, A549, MCF7, PC3 and Hep3B) and one normal cell lines (e. g., FL) were investigated along with their mode of interactions with CT-DNA. Most of the enamine derivatives with IC50 values of 86–168 μM demonstrated much stronger antiproliferative activity than the starting molecules against the cancer cells. While, among the enamine derivatives, four compounds displayed higher cytotoxic potency than the control drugs (5-fluorouracil and cisplatin) against the Hep3B cell lines, these compounds did not exhibit any significant toxicity against normal cells, FL. The UV/VIS spectral data suggest that eight compounds cause hypochromism with a slight bathochromic shift (~6 nm), indicating that they bind to the DNA by way of an intercalative or minor groove binding mode. The binding constants of the compounds are in the range of 0.1×103 M?1–2.3×104 M?1. The antiproliferative activity of studied enamine derivatives could possibly be due to their DNA binding as well as their cytotoxic properties. In addition to these assays, the chalcones and enamine derivatives were investigated by molecular docking to calculate the synergistic effect of antiproliferative activities against six human cancer cell lines.
- Burcu Gürdere, Meliha,Aydin, Ali,Yencilek, Belk?z,Ertürk, Fatih,?zbek, O?uz,Erkan, Sultan,Budak, Yakup,Ceylan, Mustafa
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- Synthesis, characterization and molecular docking of 1,2,4-triazole derivatives as potential antimicrobial agents
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In this study, a new series of (E)-N-(4-(3-(3,5-dialkylphenyl)acryloyl)phenyl)-2-(1H-1,2,4-triazol-1-yl)acetamide (32-41) was synthesized, characterized by FT-IR, 1H NMR, 13C NMR and Mass spectral analysis and evaluated for their in
- Kalaivani, Panneerselvam,Arikrishnan, Jayaraman,Gopalakrishnan, Mannuthusamy
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p. 1437 - 1442
(2020/06/09)
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- Synthesis and biological evaluation of amino chalcone derivatives as antiproliferative agents
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Chalcone is a common scaffold found in many biologically active compounds. The chalcone scaffold was also frequently utilized to design novel anticancer agents with potent biological efficacy. Aiming to continue the research of effective chalcone derivatives to treat cancers with potent anticancer activity, fourteen amino chalcone derivatives were designed and synthesized. The antiproliferative activity of amino chalcone derivatives was studied in vitro and 5-Fu as a control group. Some of the compounds showed moderate to good activity against three human cancer cells (MGC-803, HCT-116 and MCF-7 cells) and compound 13e displayed the best antiproliferative activity against MGC-803 cells, HCT-116 cells and MCF-7 cells with IC50 values of 1.52 μM (MGC-803), 1.83 μM (HCT-116) and 2.54 μM (MCF-7), respectively which was more potent than the positive control (5-Fu). Further mechanism studies were explored. The results of cell colony formatting assay suggested compound 10e inhibited the colony formation of MGC-803 cells. DAPI fluorescent staining and flow cytometry assay showed compound 13e induced MGC-803 cells apoptosis. Western blotting experiment indicated compound 13e induced cell apoptosis via the extrinsic/intrinsic apoptosis pathway in MGC-803 cells. Therefore, compound 13e might be a valuable lead compound as antiproliferative agents and amino chalcone derivatives worth further effort to improve amino chalcone derivatives’ potency.
- Gu, Yu-Fan,Hu, Yang-Yang,Jin, Min-Jie,Li, Hong-Li,Li, Qian-Yu,Li, Qing-Rong,Li, Yin-Ru,Lu, Chao-Fan,Mu, Zhao-Yang,Pang, Xiao-Jing,Song, Jian,Wang, Sheng-Hui,Zhang, Sai-Yang,Zhang, Yan-Bing,Zhu, Ting
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- EGFR inhibitors and apoptotic inducers: Design, synthesis, anticancer activity and docking studies of novel xanthine derivatives carrying chalcone moiety as hybrid molecules
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One of the helpful ways to improve the effectiveness of anticancer agents and weaken drug resistance is to use hybrid molecules. therefore, the current study intended to introduce 20 novel xanthine/chalcone hybrids 9–28 of promising anticancer activity. Compounds 10, 11, 13, 14, 16, 20 and 23 exhibited potent inhibition of cancer cells growth with IC50 ranging from 1.0 ± 0.1 to 3.5 ± 0.4 μM compared to doxorubicin with IC50 ranging from 0.90 ± 0.62 to 1.41 ± 0.58 μM and that compounds 11 and 16 were the best. To verify the mechanism of their anticancer activity, compounds 10, 11, 13, 14, 16, 20 and 23 were evaluated for their EGFR inhibitory effect. The study results revealed that compound 11 showed IC50 = 0.3 μM on the target enzyme which is more potent than staurosporine reference drug (IC50 = 0.4 μM). Accordingly, the apoptotic effect of the most potent compounds 11 was extensively investigated and showed a marked increase in Bax level up to 29 folds, and down-regulation in Bcl2 to 0.28 fold, in comparison to the control. Furthermore, the effect of compound 11 on Caspases 3 and 8 was evaluated and was found to increase their levels by 8 and 14 folds, respectively. Also, the effect of compound 11 on the cell cycle and its cytotoxic effect were examined. Moreover, a molecular docking study was adopted to confirm mechanism of action.
- Abou-Zied, Hesham A.,Youssif, Bahaa G.M.,Mohamed, Mamdouh F.A.,Hayallah, Alaa M.,Abdel-Aziz, Mohamed
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- Antiproliferative activity and p53 upregulation effects of chalcones on human breast cancer cells
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Chalcones are valuable structures for drug discovery due to their broad bioactivity spectrum. In this study, we evaluated 20 synthetic chalcones against estrogen-receptor-positive breast cancer cells (MCF-7 line) and triple-negative breast cancer (TNBC) cells (MDA-MB-231 line). Antiproliferative screening by MTT assay resulted in two most active compounds: 2-fluoro-4’-aminochalcone (11) and 3-pyridyl-4’-aminochalcone (17). Their IC50 values ranged from 13.2 to 34.7?μM against both cell lines. Selected chalcones are weak basic compounds and maintained their antiproliferative activity under acidosis conditions (pH 6.7), indicating their resistance to ion-trapping effect. The mode of breast cancer cells death was investigated and chalcones 11 and 17 were able to induce apoptosis rather than necrosis in both lines. Antiproliferative target investigations with MCF-7 cells suggested 11 and 17 upregulated p53 protein expression and did not affect Sp1 protein expression. Future studies on chalcones 11 and 17 can define their in vivo therapeutic potential.
- dos Santos, Mariana Bastos,Bertholin Anselmo, Daiane,de Oliveira, Jéssica Gisleine,Jardim-Perassi, Bruna V.,Alves Monteiro, Diego,Silva, Gabriel,Gomes, Eleni,Lucia Fachin, Ana,Marins, Mozart,de Campos Zuccari, Débora Aparecida Pires,Octavio Regasini, Luis
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p. 1093 - 1099
(2019/06/06)
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- 3-Aminomethyl pyridine chalcone derivatives: Design, synthesis, DNA binding and cytotoxic studies
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Herein we report design, synthesis, and anticancer activity of compounds 6a–h and 11a–j. Compounds 6a–f were designed based on 3-aminomethyl pyridine attached to different acetamide derivatives and in compounds 6g–h it was attached to coumarin moiety. Coumarin containing compounds 6g–h showed very poor anticancer activity against both A549 (Lungs cancer cell line), and MCF-7 (Breast cancer cell line) cell lines in MTT assay. Compounds 11a–j were designed as derivatives of 3-aminomethyl pyridine and 4-amino chalcones. A series of chalcone derivatives of 3-aminomethyl pyridine 11a–j have been synthesized and screened for their in vitro anticancer activity and DNA binding affinity. Most of the compounds showed very good antimitotic activity against A549 cell line as compared to fluorouracil. Compounds 11g and 11i were selected for DNA-binding studies as they showed excellent activity against cancer cell lines in MTT assay. CT-DNA binding affinity of compounds 11g and 11i have been investigated by UV based DNA titration and fluorescence emission study against DNA-EtBr complex. Interestingly, compound 11i has displayed excellent antiproliferative activity, with IC50 0.0067?±?0.0002?μm, against MCF-7 cell line. Compound 11i has been studied for its cytotoxicity using MTT, LDH, as well as EtBr/AO assay and was found to induce apoptosis in the cancerous cell line.
- Durgapal, Sunil Dutt,Soni, Rina,Umar, Shweta,Suresh, Balakrishnan,Soman, Shubhangi S.
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p. 1279 - 1287
(2018/06/29)
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- Synthesis and antibacterial evaluation of novel cationic chalcone derivatives possessing broad spectrum antibacterial activity
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There is an urgent need to identify new antibiotics with novel mechanisms that combat antibiotic resistant bacteria. Herein, a series of chalcone derivatives that mimic the essential properties of cationic antimicrobial peptides were designed and synthesized. Antibacterial activities against drug-sensitive bacteria, including Staphylococcus aureus, Enterococcus faecalis, Escherichia coli and Salmonella enterica, as well as clinical multiple drug resistant isolates of methicillin-resistant S. aureus (MRSA), KPC-2-producing and NDM-1-producing Carbapenem-resistant Enterobacteriaceae were evaluated. Representative compounds 5a (MIC: 1 μg/mL against S. aureus, 0.5 μg/mL against MRSA) and 5g (MIC: 0.5 μg/mL against S. aureus, 0.25 μg/mL against MRSA) showed good bactericidal activity against both Gram-positive and Gram-negative bacteria, including the drug-resistant species MRSA, KPC and NDM. These membrane-active antibacterial compounds were demonstrated to reduce the viable cell counts in bacterial biofilms effectively and do not induce the development of resistance in bacteria. Additionally, these representative molecules exhibited negligible toxicity toward mammalian cells at a suitable concentration. The combined results indicate that this series of cationic chalcone derivatives have potential therapeutic effects against bacterial infections.
- Chu, Wen-Chao,Bai, Peng-Yan,Yang, Zhao-Qing,Cui, De-Yun,Hua, Yong-Gang,Yang, Yi,Yang, Qian-Qian,Zhang, En,Qin, Shangshang
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supporting information
p. 905 - 921
(2017/12/26)
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- Synthesis, docking studies and: In vitro evaluation of novel chalcones as potent inhibitors of phosphodiesterase 5 from human platelets and 5A from bovine recombinant
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A series of new nitric oxide donor chalcone moieties were synthesized and evaluated for phosphodiesterase 5 (PDE 5) and 5A (PDE 5A) inhibition potential from human plasma and bovine recombinant, respectively. Molecular docking showed an excellent binding
- Sherikar, Amol S.,Dhavale, Rakesh P.,Bhatia, Manish S.
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p. 14365 - 14385
(2018/08/28)
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- Design, Synthesis, and Antiviral Activity of Novel Chalcone Derivatives Containing a Purine Moiety
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To find new antiviral agents, novel chalcone derivatives containing a purine moiety were designed and synthesized by combining bioactive substructures. The antiviral activities of the derivatives against tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV) were evaluated. Results showed that most of the derivatives showed antiviral activities. Compounds 3n and 3p exhibited excellent curative, protective and inactivation activities against TMV, with the EC50 values of 452.4, 416.2, 241.2 and 438.7, 418.6, 261.7 μg?mL?1, respectively, which were better than those of ribavirin (585.8, 436.0 and 268.7 μg?mL?1). Compounds 3n and 3p showed remarkable curative and protective activities against CMV. Compound 3n showed a moderate affinity to TMV coat protein, with binding constant Ka and Kd values of 1.5 × 104 L?mol?1 and 79.8 μmol?L?1, respectively. These findings provided an important structural insight for further designs of highly active chalcone derivatives and a basis for further study on their mechanism of action.
- Gan, Xiuhai,Wang, Yanjiao,Hu, Deyu,Song, Baoan
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p. 665 - 672
(2017/05/29)
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- Antiproliferative and pro-apoptotic activities of 2′- and 4′-aminochalcones against tumor canine cells
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In the present study, a series of 2′- and 4′-aminochalcones were synthesized and their antiproliferative activity against a canine malignant histiocytic cell line (DH82) was evaluated. Particularly aminochalcones with a hydrophobic substituent on ring B proved to be potent antiproliferative agents. Among these compounds, aminochalcones 3, 4 and 11 inhibited the growth of DH82 cells, with IC50 values of 34.4, 31.4 and 38.2 μM, respectively, and were three times more potent than etoposide (IC50 = 95.5 μM). The selected chalcones induced death through apoptosis rather than necrosis in DH82 and non-tumorigenic Madin-Darby canine kidney cells (MDCK). Further experiments suggested that the aminochalcones interfere with the regulation of oncogenes/tumor suppressor genes. Aminochalcone 11 inhibited transcription of the TOPOIIα and TP53 genes and aminochalcone 4 down-regulated Sp1 protein expression in a concentration-dependent manner.
- Santos, Mariana B.,Pinhanelli, Vitor C.,Garcia, Mayara A.R.,Silva, Gabriel,Baek, Seung J.,Fran?a, Suzelei C.,Fachin, Ana L.,Marins, Mozart,Regasini, Luis O.
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p. 884 - 889
(2017/07/24)
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- Naphthoquinone-based chalcone hybrids and derivatives: Synthesis and potent activity against cancer cell lines
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Novel naphthoquinone-based chalcones were prepared from the reaction between 3-bromo-nor-β-lapachone and amino-chalcones. Lapachone derivatives are also described here. All the substances were evaluated against cancer and normal cell lines and several compounds demonstrated potent antitumor activity. This journal is
- Jardim, Guilherme A. M.,Guimares, Tiago T.,Pinto, Maria Do Carmo F.R.,Cavalcanti, Bruno C.,De Farias, Kaio M.,Pessoa, Claudia,Gatto, Claudia C.,Nair, Divya K.,Namboothiri, Irishi N. N.,Da Silva Jnior, Eufrnio N.
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p. 120 - 150
(2015/02/02)
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- On the investigation of hybrid quinones: Synthesis, electrochemical studies and evaluation of trypanocidal activity
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In our continued search for novel trypanocidal compounds, arylamine, chalcone, triazolic, triazole-carbohydrate and chalcogenium derivatives containing a naphthoquinone scaffold were prepared; in addition to electrochemical studies, these compounds were evaluated against the infective bloodstream form of Trypanosoma cruzi, the etiological agent of Chagas disease. Among the thirty-eight compounds herein evaluated, six were found to be more potent against trypomastigotes than the standard drug benznidazole, with IC50/24 h values between 52.9 and 89.5 μM.
- Jardim, Guilherme A. M.,Reis, Wallace J.,Ribeiro, Matheus F.,Ottoni, Flaviano M.,Alves, Ricardo J.,Silva, Thaissa L.,Goulart, Marilia O. F.,Braga, Antonio L.,Menna-Barreto, Rubem F. S.,Salom?o, Kelly,De Castro, Solange L.,Da Silva Júnior, Eufranio N.
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p. 78047 - 78060
(2015/09/28)
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- Discovery of novel AHLs as potent antiproliferative agents
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Three series of novel AHL analogs were synthesized and evaluated for their in vitro cytotoxic activity against four human cancer cell lines. The SARs investigation indicated that AHLs with a terminal phenyl group, especially those with the chalcone scaffold had remarkably enhanced cytotoxicity than those with the hydrophobic side chains. Besides, some of these compounds were much more potent than 5-Fu and natural OdDHL. Through the detailed SARs discussions, we found that compounds 10a-k and 14 with the 4-amino chalcone scaffold showed excellent inhibition against all the tested cancer cell lines and were much more potent than 5-Fu and AHLs. Such scaffold may act as a template for further lead optimization. Compound 10i with a 3, 4, 5-trimethoxy group was the most potent one against all the tested cancer cell lines. Flow cytometry analysis indicated that analog 11e induced the cellular apoptosis and cell cycle arrest of MCF-7 cells at G2/M phase in a concentration-and time-dependent manner.
- Ren, Jing-Li,Zhang, Xu-Yao,Yu, Bin,Wang, Xi-Xin,Shao, Kun-Peng,Zhu, Xiao-Ge,Liu, Hong-Min
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p. 321 - 329
(2015/03/04)
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- In vitro antioxidant activity and scavenging effects of some synthesized 4-Aminochalcones
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A new series of substituted 4'-aminochalcones were synthesized by Claisen-Schmidt condensation of 4-aminoacetophenone with various substituted aromatic/heteroaromatic aldehydes. The antioxidant activity for all these compounds were studied on various reac
- Prasad, Y.Rajendra,Rani, V. Jhansi,Rao, A. Srinivasa
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- Synthesis of amino chalcones in presence of ionic liquid as soluble support
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A microwave-assisted liquid phase synthesis of aminochalcones was developed by using aldehyde-functionalized ionic liquid as soluble support. Ionic liquid bound aminoacetophenone was treated with aromatic aldehyde to give supported chalcone derivatives. After cleavage, the target compounds were obtained in 83-92 % yields and ≥ 95 % purities without column chromatographic purification. The recovered aldehyde-functionalized ionic liquid could be reused for several times without affecting its activity and the yields of desired compounds were between 86-89 %. These results indicated that the presented method could be applied efficiently to the liquid phase combinatorial chemistry based on aldol condensation.
- Pan, Xianhua,Yi, Fengping,Zhang, Xuan,Chen, Shihong
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experimental part
p. 3809 - 3813
(2012/09/07)
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- Antimicrobial and cytotoxicity potential of acetamido, amino and nitrochalcones
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Background: Chalcones constitute one of the major classes of natural products belonging to the flavonoid family, and they have been reported as having a range of important therapeutic activities, including some chalcones are effective as antimicrobial agents. Currently, the search for new structures with antimicrobial activity has been intensified due to the emergence of many strains resistant to antibiotics currently used to treat infectious diseases. Method: 3 chalcone series (amino, acetamido and nitrochalcones) were prepared (23 compounds) and evaluated for their antimicrobial and cytotoxic potential. The effects of substituents on their respective activities also was evaluated. Results & Conclusion: The results showed that 4 aminochalcones (2, 4, 8, 9), 3 acetoamidochalcones (10, 14, 18) and 3 nitrochalcones (20, 22, 23), exhibited antifungal effects. The aminochalcones were more toxic than the acetamidochalcones, while the nitrochalcones did not present any toxic effect. It was verified that there seems to be structure-activity correlation in some electron-donating and withdrawing substituents groups in rings A and B of the synthetized chalcone analogues and its antifungal and cytotoxic activity. Georg Thieme Verlag KG Stuttgart New York.
- Trist?o,Campos-Buzzi,Corrêa,Cruz,Cechinel Filho,Bella Cruz
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supporting information
p. 590 - 594
(2013/03/13)
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- A study of anti-inflammatory and analgesic activity of new 2,4,6-trisubstituted pyrimidines
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Chalcone derivatives (3a - m) were prepared by condensing 4-aminoacetophenone with various substituted aromatic and hetero aromatic aldehydes according to Claisen-Schmidt condensation. These chalcones, on reaction with guanidine hydrochloride under basic alcoholic conditions gave 2,4,6-trisubstituted pyrimidines (5a - m) in quantitative yields. All the newly synthesized pyrimidines were characterized by means of IR, 1H- and 13CNMR, Electron Ionization (EI)-mass and elemental analyses and screened for anti-inflammatory and analgesic activities by in vivo. 2-Amino-4-(4-aminophenyl)-6-(2,4-dichlorophenyl)pyrimidine (5b) and 2-amino-4-(4-aminophenyl)- 6-(3-bromophenyl) pyrimidine (5d) were found to be the most potent anti-inflammatory and analgesic activity compared with ibuprofen, reference standard. And also it was found that compound 5b identified as lead structure among all in both the activities. Pyrimidines which showed good anti-inflammatory activity also displayed better analgesic activity.
- Yejella, Rajendra Prasad,Atla, Srinivasa Rao
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scheme or table
p. 1079 - 1082
(2011/10/05)
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- Synthesis and antimicrobial activity of some new 2,4,6-trisubstituted pyrimidines
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Chalcone derivatives [3(a-m)] were prepared by condensing 4-aminoacetophenone with various substituted aromatic and hetero aromatic aldehydes in dilute ethanolic potassium hydroxide solution at room temperature according to Claisen-Schmidt condensation. These chalcones react with guanidine hydrochloride in a basic alcoholic media to give 2,4,6-trisubstituted pyrimidines [5(a-m)]. All these pyrimidines were characterized by means of their IR, 1H NMR and elemental analyses and screened for their antimicrobial activity. Some of these compounds showed significant antimicrobial activity.
- Prasad, Y. Rajendra,Rao, B. Bhaskar,Agarwal,Rao, A. Srinivasa
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scheme or table
p. 641 - 644
(2011/12/15)
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- Synthesis and analgesic activity of some chalcones
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A series of novel 1-(4′-aminophenyl)-3-(substituted aryl/heteroaryl)-2-propen-1-ones (1-16) have been synthesized by treating 4-amino acetophenone with various substituted aromatic and unsubstituted heterocyclic aldehydes in presence of methanol and aqueous alkaline solution at room temperature. Their structures were confirmed by IR, 1H NMR, 13C NMR, EI-MS spectra and elemental analyses data. The synthesized compounds were investigated for their analgesic activity. Compounds 6 and 15 exhibited maximum analgesic activity. Chalcones with electron releasing substituent like amino, hydroxyl, methyl, halogens etc exhibited good analgesic activity.
- Srinivasa Rao
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experimental part
p. 4373 - 4376
(2012/02/14)
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- Synthesis of new chalcone derivatives containing acridinyl moiety with potential antimalarial activity
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A series of novel chalcones bearing acridine moiety attached to the amino group in their ring A have been synthesized through noncatalyzed nucleophilic aromatic substitution reaction between various 3′-aminochalcone or 4′-aminochalcones and 9-chloroacridine. The synthesized chalcone derivatives have been characterized and screened for in vitro antimalarial activity against Plasmodium falciparum NF-54. All the chalcones showed complete inhibition at concentration of 10 μg/mL and above while three compounds showed significant inhibition at concentration of 2 μg/mL. The three most active chalcone derivatives were screened for in vivo activity as well, but no significant inhibition in parasitaemia was observed when given intraperitoneally to Plasmodium yoelii infected mice model.
- Tomar,Bhattacharjee,Kamaluddin,Rajakumar,Srivastava, Kumkum,Puri
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scheme or table
p. 745 - 751
(2010/04/04)
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- Screening of biological activities of a series of chalcone derivatives against human pathogenic microorganisms
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In an effort to develop new antimicrobial agents, a series of chalcone derivatives, 3-60, were prepared by Claisen-Schmidt condensation of appropriate acetophenones and 2-furyl methyl ketones with appropriate aromatic aldehydes, furfural, and thiophene-2-carbaldehyde in an aqueous solution of NaOH and EtOH at room temperature. The synthesized compounds were characterized by means of their IR- and NMR-spectral data, and elemental analysis. All compounds were tested for their antibacterial and antifungal activities by the disc diffusion method. For the most active compounds, also minimum inhibitory concentrations (MICs) were determined.
- Karaman, Isa,Gezegen, Hayreddin,Guerdere, M. Burcu,Dingil, Alparslan,Ceylan, Mustafa
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experimental part
p. 400 - 408
(2010/09/04)
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- The synthesis and structure-activity relationship of substituted N-phenyl anthranilic acid analogs as amyloid aggregation inhibitors
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It is believed that β-amyloid aggregation is an important event in the development of Alzheimer's disease. In the course of our studies to identify β-amyloid aggregation inhibitors, a series of N-phenyl anthranilic acid analogs were synthesized and studied for β-amyloid inhibition activity. The synthesis, structure-activity relationship, and in vivo activity of these analogs are discussed.
- Simons, Lloyd J.,Caprathe, Bradley W.,Callahan, Michael,Graham, James M.,Kimura, Takenori,Lai, Yingjie,LeVine III, Harry,Lipinski, William,Sakkab, Annette T.,Tasaki, Yoshikazu,Walker, Lary C.,Yasunaga, Tomoyuki,Ye, Yuyang,Zhuang, Nian,Augelli-Szafran, Corinne E.
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scheme or table
p. 654 - 657
(2009/09/06)
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- Solid phase synthesis of aminochalcones
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A microwave-assisted solid phase synthesis of aminochalcones via the Claisen-Schmidt condensation reaction between resin-bound p-aminoacetophenone and aromatic aldehydes was described.
- Yi, Fengping,Peng, Yanqing,Song, Gonghua,Li, Jizong
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p. 311 - 312
(2007/10/03)
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