Nivetha Narayanasamy, Martiz Reshma Mary, Patil Shashank M, Ramu Ramith, Sreenivasa Swamy, Velmathi Sivan
Organic and Polymer Synthesis Laboratory, Department of Chemistry, National Institute of Technology Tiruchirappalli 620 015 Tamil Nadu India
Department of Biotechnology and Bioinformatics, School of Life Sciences, JSS Academy of Higher Education and Research Mysuru 570 015 Karnataka India.
RSC Adv. 2022 Aug 25;12(37):24192-24207. doi: 10.1039/d2ra04452h. eCollection 2022 Aug 22.
A highly stereoselective, three-component method has been developed to synthesize pyrrolidine and pyrrolizidine containing spirooxindole derivatives. The interaction between the dipolarophile α,β-unsaturated carbonyl compounds and the dipole azomethine ylide formed by the reaction of 1,2-dicarbonyl compounds and secondary amino acids is referred to as the 1,3-dipolar cycloaddition reaction. The reaction conditions were optimized to achieve excellent stereo- and regioselectivity. Shorter reaction time, simple work-up and excellent yields are the salient features of the present approach. Various spectroscopic methods and single crystal X-ray diffraction examinations of one example of compound 6i validated the stereochemistry of the expected products. The anti-diabetic activity of the newly synthesized spirooxindole derivatives was tested against the α-glucosidase and α-amylase enzymes. Compound 6i was found to exhibit potent inhibition activity against α-glucosidase and α-amylase enzymes which is further evidenced by molecular docking studies.
已开发出一种高度立体选择性的三组分方法来合成含螺环氧化吲哚衍生物的吡咯烷和吡咯里西啶。亲偶极体α,β-不饱和羰基化合物与由1,2-二羰基化合物和仲氨基酸反应形成的偶极体甲亚胺叶立德之间的相互作用被称为1,3-偶极环加成反应。对反应条件进行了优化以实现优异的立体和区域选择性。反应时间短、后处理简单和产率优异是本方法的显著特点。对化合物6i的一个实例进行的各种光谱方法和单晶X射线衍射检测验证了预期产物的立体化学。对新合成的螺环氧化吲哚衍生物的抗糖尿病活性针对α-葡萄糖苷酶和α-淀粉酶进行了测试。发现化合物6i对α-葡萄糖苷酶和α-淀粉酶表现出强效抑制活性，分子对接研究进一步证明了这一点。
