α-芳酰基代烯二硫缩醛介导的(E)-3-(苯并[d]噻唑-2-基氨基)-2-(1-甲基-1H-吲哚-3-甲酰基)-3-(甲基硫代)丙烯腈衍生物的合成及其生物评价。
α-Aroylketene Dithioacetal Mediated Synthesis of (E)-3-(benzo[d]thiazol-2-ylamino)-2-(1-methyl-1H-indole-3-carbonyl)-3-(methylthio)acrylonitrile Derivatives and their Biological Evaluation.
机构信息
School of Chemical Sciences, Solapur University, Solapur-413 255, Maharashtra, India.
Department of Chemistry, Yeshwantrao Chavan Mahavidyalaya, Tuljapur, Dist-Osmanabad-413 601, Maharashtra, India.
出版信息
Anticancer Agents Med Chem. 2018;18(5):757-764. doi: 10.2174/1871520617666170912124258.
BACKGROUND
The blending of two pharmacophores would generate novel molecular templates that are likely to exhibit interesting biological properties.
OBJECTIVE
A facile, efficient and high yielding synthesis of (E)-3-(benzo[d]thiazol-2-ylamino)-2-(1-methyl-1Hindole- 3-carbonyl)-3-(methylthio) acrylonitrile derivatives and evaluation of therapeutic potential.
METHOD
The synthesis of target molecules has been achieved by reacting 2-aminobenzothiazole and substituted 2-(1-methyl-1H-indole-3-carbonyl)-3,3-bis(methylthio)acrylonitrile in the presence of a catalytic amount of sodium hydride in THF. Structural investigations were carried using 1H NMR, 13C NMR, FT-IR, and HRMS data.
RESULTS
In vitro anti-tumor evaluation of the synthesized compounds against MCF-7 (breast carcinoma) cell line revealed that they possess good anti-tumor activities. Compounds, 4j and 4i demonstrated significant activities against breast carcinoma (GI50 14.3 and 19.5 µM respectively). Most of the synthesized compounds were also found to be excellent NO, H2O2, DPPH, and superoxide radical scavengers. Anti-diabetic and antiinflammatory evaluation also displayed moderate activity.
CONCLUSION
Among the compounds synthesized some of the compounds possess significant anticancer, antioxidant and anti-inflammatory properties.
背景
两种药效团的混合将产生新的分子模板，这些模板很可能表现出有趣的生物学特性。
目的
以简便、高效、高产的方式合成（E）-3-（苯并[d]噻唑-2-基氨基）-2-（1-甲基-1H-吲哚-3-羰基）-3-（甲基硫代）丙烯腈衍生物，并评估其治疗潜力。
方法
在 THF 中，用少量的氢化钠使 2-氨基苯并噻唑与取代的 2-（1-甲基-1H-吲哚-3-羰基）-3,3-双（甲基硫代）丙烯腈反应，从而合成目标分子。使用 1H NMR、13C NMR、FT-IR 和 HRMS 数据进行结构研究。
结果
对合成的化合物进行体外抗肿瘤活性评价，发现它们对 MCF-7（乳腺癌）细胞系具有良好的抗肿瘤活性。化合物 4j 和 4i 对乳腺癌表现出显著的活性（GI50 分别为 14.3 和 19.5 μM）。大多数合成的化合物还被发现是极好的 NO、H2O2、DPPH 和超氧自由基清除剂。抗糖尿病和抗炎评价也显示出中等活性。
结论
在所合成的化合物中，一些化合物具有显著的抗癌、抗氧化和抗炎特性。
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