碘催化合成咪唑并[1,2 - ]吡嗪和咪唑并[1,2 - ]吡啶衍生物及其抗癌活性。
Iodine catalyzed synthesis of imidazo[1,2-]pyrazine and imidazo[1,2-]pyridine derivatives and their anticancer activity.
作者信息
Krishnamoorthy Rajavenkatesh, Anaikutti Parthiban
机构信息
Organic and Bioorganic Chemistry Laboratory, CSIR-Central Leather Research Institute (CSIR-CLRI) Adyar Chennai Tamil Nadu-600020 India
Centre for GMP, National Institute of Pharmaceutical Education and Research (NIPER-G) Guwahati Assam-781101 India
出版信息
RSC Adv. 2023 Dec 13;13(51):36439-36454. doi: 10.1039/d3ra07842f. eCollection 2023 Dec 8.
An efficient iodine-catalyzed method for synthesizing imidazo[1,2-]pyrazines and imidazo[1,2-]pyridines one-pot three-component condensations has been reported. The product, generated by the reaction between an aryl aldehyde and 2-aminopyridine or 2-aminopyrazine, undergoes [4 + 1] cycloaddition with -butyl isocyanide, affording the corresponding imidazopyrazine and imidazopyridine derivatives in good yields. The photophysical properties of these new fluorescent derivatives are also presented. The anti-cancer activities of the synthesized compounds (10a-m) and (12a-l) were evaluated against four cancer cells (Hep-2, HepG2, MCF-7, A375) and the normal Vero cell. Significant anti-cancer activities were observed and compared with the standard drug Doxorubicin. experimental results revealed that compound 12b is a promising lead with IC values of 11 μM, 13 μM, 11 μM, 11 μM, and 91 μM against Hep-2, HepG2, MCF-7, A375, and Vero, respectively.
已报道了一种高效的碘催化合成咪唑并[1,2 - ]吡嗪和咪唑并[1,2 - ]吡啶的一锅三组分缩合方法。由芳基醛与2 - 氨基吡啶或2 - 氨基吡嗪反应生成的产物，与异丁基异腈发生[4 + 1]环加成反应，以良好的产率得到相应的咪唑并吡嗪和咪唑并吡啶衍生物。还介绍了这些新型荧光衍生物的光物理性质。评估了合成化合物(10a - m)和(12a - l)对四种癌细胞（Hep - 2、HepG2、MCF - 7、A375）和正常Vero细胞的抗癌活性。观察到显著的抗癌活性，并与标准药物阿霉素进行了比较。实验结果表明，化合物12b是一种有前景的先导化合物（lead），对Hep - 2、HepG2、MCF - 7、A375和Vero的IC值分别为11 μM、13 μM、11 μM、11 μM和91 μM。
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