3,5-二羟基-7,8-二甲氧基-2-(4-甲氧基苯基)苯并吡喃-4-酮衍生物作为抗癌剂的合成
Synthesis of 3,5-dihydroxy-7,8-dimethoxy-2-(4-methoxyphenyl)benzopyran-4-one derivatives as anticancer agents.
作者信息
Singh Sarita, Ahmad Ateeque, Raghuvanshi Dushyant Singh, Hasanain Mohammad, Agarwal Karishma, Dubey Vijaya, Fatima Kaniz, Alam Sarfaraz, Sarkar Jayanta, Luqman Suaib, Khan Feroz, Tandon Sudeep, Gupta Atul
机构信息
Medicinal Chemistry Department, CSIR-Central Institute of Medicinal and Aromatic Plants, PO CIMAP, Kukrail Road, Lucknow 226015, India.
Process Chemistry and Technology Department, CSIR-Central Institute of Medicinal and Aromatic Plants, PO CIMAP, Kukrail Road, Lucknow 226015, India.
出版信息
Bioorg Med Chem Lett. 2016 Nov 1;26(21):5322-5327. doi: 10.1016/j.bmcl.2016.09.036. Epub 2016 Sep 15.
Different alkyl amide (15a-l) and alkyl amine (16a-e) derivatives of 7,8-dimethoxy-3-hydroxy-2-(4-methoxyphenyl)benzopyran-4-one were synthesized and evaluated for their anticancer activity against five different cancer cell lines using SRB assay. Compounds 15e, 15i, 15j and 16a-e showed significant anticancer activity within the range of IC 2.58-34.86μM. The most promising molecule, 16c, was further analyzed for its effect on cell cycle and apoptosis of estrogen receptor positive cancer cells (MCF-7 cells) which showed that 16c triggered apoptosis in MCF-7 cells and arrested cells population at sub-G (apoptotic) and GM phase. In tubulin polymerization assay, 16c interfered with kinetics of tubulin polymerization.
合成了7,8-二甲氧基-3-羟基-2-(4-甲氧基苯基)苯并吡喃-4-酮的不同烷基酰胺(15a-l)和烷基胺(16a-e)衍生物，并使用SRB法评估了它们对五种不同癌细胞系的抗癌活性。化合物15e、15i、15j和16a-e在IC 2.58-34.86μM范围内表现出显著的抗癌活性。对最有前景的分子16c进一步分析了其对雌激素受体阳性癌细胞(MCF-7细胞)的细胞周期和凋亡的影响，结果表明16c触发了MCF-7细胞的凋亡，并使细胞群体停滞在亚G(凋亡)期和G1期。在微管蛋白聚合试验中，16c干扰了微管蛋白聚合的动力学。
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