Khan Momin, Yousaf Muhammad, Wadood Abdul, Junaid Muhammad, Ashraf Muhammad, Alam Umber, Ali Muhammad, Arshad Muhammad, Hussain Zahid, Khan Khalid Mohammed
Department of Chemistry, Abdul Wali Khan University, Mardan 23200, Pakistan.
Department of Chemistry, Abdul Wali Khan University, Mardan 23200, Pakistan.
Bioorg Med Chem. 2014 Jul 1;22(13):3441-8. doi: 10.1016/j.bmc.2014.04.033. Epub 2014 Apr 29.
A series of 6-chloro-3-oxindole derivatives 1-25 were synthesized in high yields by the reaction of 6-chlorooxindole with different aromatic aldehydes in the presence of piperidine. All the synthesized compounds were isolated with E configuration. The structures were confirmed using spectroscopic techniques, including (1)H NMR and EIMS. These compounds showed varying degree of yeast α-glucosidase inhibition and seven were found as potent inhibitors of the enzyme. Compounds 2, 3, 4, 5, 6, 23, and 25 exhibited IC50 values 2.71±0.007, 11.41±0.005, 37.93±0.002, 15.19±0.004, 24.71±0.007, 17.33±0.001, and 14.2±0.002μM, respectively, as compared to standard acarbose (IC50, 38.25±0.12μM). Docking studies helped to find interactions between the enzyme and the active compounds. As a result of this study, oxindoles have been discovered as a new class of α-glucosidase inhibitors which have not been reported earlier.
通过6-氯氧化吲哚与不同芳香醛在哌啶存在下反应，以高产率合成了一系列6-氯-3-氧化吲哚衍生物1-25。所有合成的化合物均以E构型分离。使用包括¹H NMR和EIMS在内的光谱技术确认了结构。这些化合物表现出不同程度的酵母α-葡萄糖苷酶抑制作用，发现其中七种是该酶的有效抑制剂。与标准阿卡波糖（IC50，38.25±0.12μM）相比，化合物2、3、4、5、6、23和25的IC50值分别为2.71±0.007、11.41±0.005、37.93±0.002、15.19±0.004、24.71±0.007、17.33±0.001和14.2±0.002μM。对接研究有助于发现酶与活性化合物之间的相互作用。作为这项研究的结果，氧化吲哚已被发现是一类新的α-葡萄糖苷酶抑制剂，此前尚未见报道。
