- Synthesis, crystal structures, spectroscopic and nonlinear optical properties of chalcone derivatives: A combined experimental and theoretical study
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A set of chalcone compounds were prepared by reacting p-bromoacetophenone with various substituted aromatic aldehyde in ethanol using sodium ethoxide as base. The synthesized molecules were well characterized using spectroscopic techniques like UV–Vis, fo
- Arshad, Muhammad Nadeem,Al-Dies, Al-Anood M.,Asiri, Abdullah M.,Khalid, Muhammad,Birinji, Abdulhadi Salih,Al-Amry, Khalid A.,Braga, Ataualpa A.C.
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p. 142 - 156
(2017/04/03)
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- Synthesis and structure-activity relationships of chalcone derivatives as inhibitors of ovarian cancer cell growth
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Background: Ovarian cancer remains a disease with a poor five year survival rate. As such, novel therapies are needed. Natural chalcones as well as their synthetic derivatives have shown biological activity in a number of areas including the inhibition of cancer cell growth. Objective: To synthesize a library of chalcone derivatives, including novel structures, and determiner the inhibition of ovarian cancer cell growth and Structure-activity-relationships. Methods: The Claisen-Schmidt condensation reaction between substituted acetophenones and aromatic aldehydes was used to produce a series of novel chalcones in moderate to excellent yields and good purity. Cellular proliferation of CA-OV3 cells was measured with a MTS assay. Results: Out of the thirty-four synthesized compounds, eight are new derivatives. The synthesized compounds were characterized by 1H NMR, 13C NMR, and HRMS. Biological evaluation of these β-phenylacrylophenone derivatives in CA-OV3 cells showed interesting antiproliferative activities providing initial structure – activity information. Conclusion: Fourteen of the thirty-four tested compounds showed significant activity, with several showing near complete inhibition of growth at 100 μM. The structure-activity relationships suggest that modification to the A ring is widely tolerated and that electron-donating modifications to the B ring are beneficial to activity. Electron-withdrawing modifications to the B ring did not show inhibition of cell growth.
- Tucker, Zachary D.,Barrios, Francis J.,Krzysiak, Amanda J.
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p. 1259 - 1266
(2017/11/14)
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- Design, synthesis and biological evaluation of benzohydrazide derivatives containing dihydropyrazoles as potential EGFR kinase inhibitors
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A series of novel benzohydrazide derivatives containing dihydropyrazoles have been synthesized as potential epidermal growth factor receptor (EGFR) kinase inhibitors and their biological activities as potential antiproliferative agents have been evaluated. Among these compounds, compound H20 exhibited the most potent antiproliferative activity against four cancer cell line variants (A549, MCF-7, HeLa, HepG2) with IC50 values of 0.46, 0.29, 0.15 and 0.21 μM respectively, which showed the most potent EGFR inhibition activities (IC50 = 0.08 μM for EGFR). Molecular modeling simulation studies were performed in order to predict the biological activity and activity relationship (SAR) of these benzohydrazide derivatives. These results suggested that compound H20 may be a promising anticancer agent.
- Wang, Hai-Chao,Yan, Xiao-Qiang,Yan, Tian-Long,Li, Hong-Xia,Wang, Zhong-Chang,Zhu, Hai-Liang
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- Synthesis of apoptotic chalcone analogues in HepG2 human hepatocellular carcinoma cells
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Eight chalcone analogues were prepared and evaluated for their cytotoxic effects in human hepatoma HepG2 cells. Compound 5 had a potent cytotoxic effect. The percentage of apoptotic cells was significantly higher in compound 5-treated cells than in contro
- Park, Cheon-Soo,Ahn, Yongchel,Lee, Dahae,Moon, Sung Won,Kim, Ki Hyun,Yamabe, Noriko,Hwang, Gwi Seo,Jang, Hyuk Jai,Lee, Heesu,Kang, Ki Sung,Lee, Jae Wook
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supporting information
p. 5705 - 5707
(2015/11/24)
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- Synthesis and biological evaluation of compounds which contain pyrazole, thiazole and naphthalene ring as antitumor agents
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A series of compounds which contain pyrazole, thiazole and naphthalene ring (1a-7a, 1b-7b, 1c-7c, 1d-7d) were firstly synthesized and their anti-proliferative activity, EGFR inhibitory activity, cytotoxicity and inhibition to Hela cell migration were evaluated. Compound 2-(3-(3,4- dimethylphenyl)-5-(naphthalen-2-yl)-4,5-dihydro-1H-pyrazol-1-yl)thiazol-4(5H) -one (7d) displayed the most potent inhibitory activity (IC50 = 0.86 μM for Hela and IC50 = 0.12 μM for EGFR). Structure-activity relationship (SAR) analysis showed that the anti-proliferative activity was affected by A-ring-substituent (-OCH3 > -CH3 > -H > -Br > -Cl > -F). Docking simulation of compound 7d into EGFR active site showed that naphthalene ring of 7d with LYS721 formed two p-π bonds, which enhanced antitumor activity. Therefore, compound 7d may be developed as a potential antitumor agent.
- Yuan, Ji-Wen,Wang, She-Feng,Luo, Zhong-Liang,Qiu, Han-Yue,Wang, Peng-Fei,Zhang, Xin,Yang, Yong-An,Yin, Yong,Zhang, Fei,Zhu, Hai-Liang
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p. 2324 - 2328
(2014/05/20)
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- Design, modification and 3D QSAR studies of novel naphthalin-containing pyrazoline derivatives with/without thiourea skeleton as anticancer agents
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Two series of novel naphthalin-containing pyrazoline derivatives C1-C14 and D1-D14 have been synthesized and evaluated for their EGFR/HER-2 inhibitory and anti-proliferation activities. Compound D14 displayed the most potent activity against EGFR and A549
- Yang, Wen,Hu, Yang,Yang, Yu-Shun,Zhang, Fei,Zhang, Yan-Bin,Wang, Xiao-Liang,Tang, Jian-Feng,Zhong, Wei-Qing,Zhu, Hai-Liang
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p. 1050 - 1063
(2013/03/14)
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- Induction of apoptosis and cell cycle arrest in L-1210 murine lymphoblastic leukaemia cells by (2E)-3-(2-naphthyl)-1-(3′-methoxy-4′-hydroxy- phenyl)-2-propen-1-one
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Objectives New compounds with biological targets and less cytotoxicity to normal cells are necessary for cancer therapy. In this work ten synthetic chalcones derived from 2-naphtaldehyde were evaluated for their cytotoxic effect in murine acute lymphoblas
- Pedrini, Fernanda Spezia,Chiaradia, Louise Domeneghini,Licinio, Marley Aparecida,De Moraes, Ana Carolina Rabello,Curta, Juliana Costa,Costa, Aline,Mascarello, Alessandra,Creczinsky-Pasa, Tania Beatriz,Nunes, Ricardo Jose,Yunes, Rosendo Augusto,Santos-Silva, Maria Claudia
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scheme or table
p. 1128 - 1136
(2011/12/04)
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- Synthetic chalcones as efficient inhibitors of Mycobacterium tuberculosis protein tyrosine phosphatase PtpA
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In the search for lead compounds for new drugs for tuberculosis, the activity of 38 synthetic chalcones were assayed for their potential inhibitory action towards a protein tyrosine phosphatase from Mycobacterium tuberculosis - PtpA. The compounds were ob
- Chiaradia, Louise Domeneghini,Mascarello, Alessandra,Purificacao, Marcela,Vernal, Javier,Cordeiro, Marlon Norberto Sechini,Zenteno, Maria Emilia,Villarino, Andrea,Nunes, Ricardo Jose,Yunes, Rosendo Augusto,Terenzi, Hernan
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supporting information; experimental part
p. 6227 - 6230
(2009/06/30)
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