Department of Chemistry, Kakatiya University, Warangal 506 009, AP, India.
Bioorg Med Chem Lett. 2012 Jan 1;22(1):149-53. doi: 10.1016/j.bmcl.2011.11.044. Epub 2011 Nov 20.
A series of novel phenylmethylene bis-isoxazolo[4,5-b]azepine derivatives (10) have been synthesized from 3-methyl-4-nitro-5-styrylisoxazoles 6. The reaction of 6 with 3,5-dimethyl-4-nitroisoxazole (7) in piperidine afforded the Michael type adducts 8, which on treatment with different substituted chalcones in the presence of piperidine gave the Michael adducts 9. Compounds 9 underwent reductive cyclization on treatment with SnCl(2)-MeOH to afford the title compounds 10. Structure of these compounds was established on the basis of IR, (1)H NMR, (13)C NMR and Mass spectral data. The title compounds 10a-j were evaluated for in vitro and in vivo anticancer activity. Compound 10j exhibited good anticancer activity as that of standard drug Cisplatin.
一系列新型的苯亚甲基双异噁唑并[4,5-b]氮杂卓衍生物（10）已从 3-甲基-4-硝基-5-乙烯基异噁唑 6 合成得到。6 与 3,5-二甲基-4-硝基异噁唑（7）在哌啶中的反应得到迈克尔型加成物 8，8 在哌啶存在下与不同取代的查尔酮反应得到迈克尔加成物 9。9 在 SnCl(2)-MeOH 处理下进行还原环化反应得到标题化合物 10。这些化合物的结构是基于 IR、(1)H NMR、(13)C NMR 和质谱数据确定的。对标题化合物 10a-j 进行了体外和体内抗癌活性评价。化合物 10j 表现出与标准药物顺铂相当的良好抗癌活性。
