Organic Chemistry Research Laboratory, School of Chemical Sciences, Solapur University, Solapur 413 255, India.
Bioorg Med Chem. 2010 Mar 1;18(5):2060-5. doi: 10.1016/j.bmc.2009.12.077. Epub 2010 Jan 11.
A combinatorial library of beta-chlorovinyl chalcones (4) were synthesized by Claisen-Schmidt condensation reaction. Catalytic reaction of substituted 3-chloro-3-phenyl-propenal (2) and 1-(2,4-dimethoxy-phenyl)-ethanone or 1-(4-methoxy-phenyl)-ethanone (3) in alkaline conditions furnished the target compound 5-chloro-1-(2,4-dimethoxy-phenyl)-5-phenyl-penta-2,4-dien-1-one (4). The synthesized compounds were screened for their biological activity viz. anticancer, anti-inflammatory and antimicrobial activities. Synthesized compounds 4g and 4h revealed promising anti-inflammatory activity (66-67% TNF-alpha and 95-97% IL-6 inhibitory activity at 10 microM). Cytotoxicity of the compounds checked using CCK-8 cell lines and found to be nontoxic to slightly toxic. Furthermore, the anticancer activity (30-40%) was shown by compounds 4d, 4e, 4h and 4b at 10 microM concentrations against ACHN followed by Calu 1, Panc1, HCT116 and H460 cell lines. Some of the compounds 4d, 4e, 4a, 4i and 4b revealed promising antimicrobial activity at MIC 50-100 microg/mL against selected pathogenic bacteria and fungi.
通过 Claisen-Schmidt 缩合反应合成了β-氯代乙烯基查耳酮的组合文库（4）。在碱性条件下，取代的 3-氯-3-苯基丙烯醛（2）和 1-（2,4-二甲氧基苯基）-乙酮或 1-（4-甲氧基苯基）-乙酮（3）的催化反应提供了目标化合物 5-氯-1-（2,4-二甲氧基苯基）-5-苯基戊-2,4-二烯-1-酮（4）。合成的化合物被筛选其生物活性，即抗癌、抗炎和抗菌活性。合成的化合物 4g 和 4h 表现出有希望的抗炎活性（在 10 microM 时，TNF-alpha 和 IL-6 抑制活性分别为 66-67%和 95-97%）。用 CCK-8 细胞系检查化合物的细胞毒性，发现对细胞无毒或轻微毒性。此外，化合物 4d、4e、4h 和 4b 在 10 microM 浓度下对 ACHN 显示出有希望的抗癌活性（30-40%），随后是 Calu 1、Panc1、HCT116 和 H460 细胞系。一些化合物 4d、4e、4a、4i 和 4b 在 MIC 50-100 microg/mL 时对选定的病原菌和真菌表现出有希望的抗菌活性。
