Department of Chemistry, Yeshwantrao Chavan Mahavidyalaya, Tuljapur, Dist-Osmanabad-413 601, Maharashtra, India.
School of Chemical Sciences, Solapur University Solapur-413 255, Maharashtra, India.
Anticancer Agents Med Chem. 2021 Oct 28;21(16):2216-2223. doi: 10.2174/1871520621666210201095030.
Indole and pyrazole constitute a major class of biologically active scaffolds. The amalgamation of two or more pharmacophores would generate novel molecular templates that are likely to unveil remarkable biological properties.
An efficient and high yielding synthesis of indole-pyrazole integrated α-cyano substituted chalcones and their in vitro anti-breast cancer and antioxidant evaluation.
The synthesis of a series of indole-pyrazole amalgamated α-cyano substituted chalcones (6a-o) was achieved by reacting substituted 3-cyanoacetyl indole 2 with substituted pyrazole aldehyde 5 in the presence of piperidine. All the newly synthesized compounds have been characterized by IR, H NMR and HRMS spectroscopy.
Anti-breast cancer evaluation of the synthesized compounds in vitro against MCF-7 cell line revealed high anti-breast cancer activities. Amongst the compounds screened 6f, 6g, 6h, 6c, 6d, 6e, 6i and 6k unveiled excellent activity against breast carcinoma (GI <0.1μM) as good as adriamycin (GI <0.1μM). The compounds were also screened against the normal Vero monkey cell line and the results demonstrated more selectivity against MCF-7. On the other hand, compounds 6b, 6c, 6d, 6h and 6i have shown moderate DPPH and NO radical scavenging activity.
Most of the synthesized compounds exhibited significant antitumor activities. These results further support its safety margin by studying the activity on normal Vero monkey cell line. These results acclaim the possible use of these compounds for the design and development of potent anti-breast cancer agents.
吲哚和吡唑构成了一类重要的具有生物活性的支架。将两个或多个药效团融合在一起，可能会产生新的分子模板，从而揭示出显著的生物学特性。
高效高产地合成吲哚-吡唑杂合的α-氰基取代查尔酮，并对其进行体外抗乳腺癌和抗氧化评估。
在哌啶存在下，用取代的 3-氰基乙酰基吲哚 2 与取代的吡唑醛 5 反应，合成了一系列吲哚-吡唑杂合的α-氰基取代查尔酮（6a-o）。所有新合成的化合物均通过 IR、H NMR 和 HRMS 光谱进行了表征。
体外对 MCF-7 细胞系的抗乳腺癌活性评估显示，合成的化合物具有较高的抗乳腺癌活性。在所筛选的化合物中，6f、6g、6h、6c、6d、6e、6i 和 6k 对乳腺癌（GI <0.1μM）具有极好的活性，与阿霉素（GI <0.1μM）相当。这些化合物还对正常的 Vero 猴细胞系进行了筛选，结果表明对 MCF-7 具有更高的选择性。另一方面，化合物 6b、6c、6d、6h 和 6i 表现出中等的 DPPH 和 NO 自由基清除活性。
大多数合成的化合物表现出显著的抗肿瘤活性。这些结果通过研究对正常 Vero 猴细胞系的活性进一步支持了其安全性。这些结果表明，这些化合物可能用于设计和开发有效的抗乳腺癌药物。
