铁（III）催化合成甾体咪唑杂环作为强效抗增殖剂。
Fe(iii)-Catalyzed synthesis of steroidal imidazoheterocycles as potent antiproliferative agents.
作者信息
Samanta Sadhanendu, Ghosh Asim Kumar, Ghosh Sumit, Ilina Anastasia A, Volkova Yulia A, Zavarzin Igor V, Scherbakov Alexander M, Salnikova Diana I, Dzichenka Yaraslau U, Sachenko Anton B, Shirinian Valerii Z, Hajra Alakananda
机构信息
Department of Chemistry, Visva-Bharati (A Central University), Santiniketan, 731235, West Bengal, India.
出版信息
Org Biomol Chem. 2020 Aug 7;18(29):5571-5576. doi: 10.1039/d0ob01241f. Epub 2020 Jul 14.
An efficient and practical method has been developed for the synthesis of steroidal imidazoheterocycles via cost-effective and environmentally benign FeCl-catalyzed oxidative amination. A library of steroidal imidazo[1,2-a]pyridines was directly synthesized from readily available 2-aminopyridines and steroidal ketones in aerobic conditions. The synthesized compounds were screened for activity on human microsomal cytochrome P450s CYP7, CYP17 and CYP21. Antiproliferative activity of two lead compounds 3ia and 3la was additionally evaluated against the human MCF-7 (breast cancer), SKOV3 (ovarian cancer), and 22Rv1 (prostate cancer) cell lines. Steroidal imidazo[1,2-a]pyridine 3la which is a substrate molecule for CYP17A1 with IC = 1.7 μM (MCF-7), 3.0 (SKOV3), and 6.0 μM (22Rv1) has proved to be more active than reference drug cisplatin.
已开发出一种高效实用的方法，通过具有成本效益且环境友好的FeCl催化氧化胺化反应来合成甾体咪唑杂环化合物。在有氧条件下，由易得的2-氨基吡啶和甾体酮直接合成了一系列甾体咪唑并[1,2-a]吡啶。对合成的化合物进行了针对人微粒体细胞色素P450s CYP7、CYP17和CYP21活性的筛选。另外评估了两种先导化合物3ia和3la对人MCF-7（乳腺癌）、SKOV3（卵巢癌）和22Rv1（前列腺癌）细胞系的抗增殖活性。甾体咪唑并[1,2-a]吡啶3la作为CYP17A1的底物分子，其IC值分别为1.7 μM（MCF-7）、3.0（SKOV3）和6.0 μM（22Rv1），已证明其活性比参考药物顺铂更高。
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