Arasakumar Thangaraj, Mathusalini Sadasivam, Ata Athar, Shankar Ramasamy, Gopalan Subashini, Lakshmi Krishnasamy, Sakthivel Pandiyarajan, Mohan Palathurai Subramaniam
School of Chemical Sciences, Bharathiar University, Coimbatore, Tamil Nadu, 641 046, India.
Department of Chemistry, Richardson College for the Environmental Science Complex, The University of Winnipeg, 599 Portage Avenue, Winnipeg, MB, R3B 2G3, Canada.
Mol Divers. 2017 Feb;21(1):37-52. doi: 10.1007/s11030-016-9695-6. Epub 2016 Sep 26.
A series of 4-quinolone-3-carboxylic acid-containing spirooxindole-pyrrolidine derivatives was synthesized via multicomponent 1,3-dipolar cycloaddition reactions of azomethine ylides with new (E)-4-oxo-6-(3-phenyl-acryloyl)-1,4-dihydroquinoline-3-carboxylic acids in good yields with high regioselectivity. The cycloadducts were characterized by analytical and spectral data including [Formula: see text], [Formula: see text], 2D NMR and mass spectroscopy. The structure of one of the compounds (8a) was investigated theoretically by computational techniques. DFT studies support the proposed mechanism for this cycloaddition reaction. Furthermore, antibacterial activities of the new compounds were evaluated against Gram-positive and Gram-negative bacterial strains. Compounds 8f, 8m and 8p showed potent inhibition activities against selected bacteria. The in vitro cytotoxicity of spirooxindole derivatives (8a-r) was evaluated against MCF-7 breast cancer cell line. Among the various compounds tested, compound 8f [Formula: see text] showed significant cytotoxic activity compared to the standard drug doxorubicin [Formula: see text].
通过甲亚胺叶立德与新型（E）-4-氧代-6-（3-苯基丙烯酰基）-1,4-二氢喹啉-3-羧酸的多组分1,3-偶极环加成反应，以良好的产率和高区域选择性合成了一系列含4-喹诺酮-3-羧酸的螺环氧化吲哚-吡咯烷衍生物。通过包括[化学式：见原文]、[化学式：见原文]、二维核磁共振和质谱在内的分析和光谱数据对环加成产物进行了表征。采用计算技术对其中一种化合物（8a）的结构进行了理论研究。密度泛函理论研究支持了该环加成反应的 proposed 机制。此外，还评估了新化合物对革兰氏阳性和革兰氏阴性细菌菌株的抗菌活性。化合物8f、8m和8p对选定的细菌显示出强效抑制活性。评估了螺环氧化吲哚衍生物（8a-r）对MCF-7乳腺癌细胞系的体外细胞毒性。在测试的各种化合物中，与标准药物阿霉素[化学式：见原文]相比，化合物8f[化学式：见原文]显示出显著的细胞毒性活性。
