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一锅多组分合成新型色烯并[4,3-b]吡咯-3-基衍生物作为α-葡萄糖苷酶抑制剂。

One-pot multi-component synthesis of novel chromeno[4,3-b]pyrrol-3-yl derivatives as alpha-glucosidase inhibitors.

机构信息

Department of Chemistry, Faculty of Sciences, Persian Gulf University, 7516913817, Bushehr, Iran.

School of Chemistry, College of Science, Uccniversity of Tehran, P.O.Box, 14155-6455, Tehran, Iran.

出版信息

Mol Divers. 2022 Oct;26(5):2393-2405. doi: 10.1007/s11030-021-10337-w. Epub 2021 Oct 25.

DOI:10.1007/s11030-021-10337-w
PMID:34697701
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8544188/
Abstract

A green and efficient one-pot multi-component protocol was developed for the synthesis of some novel dihydrochromeno[4,3-b]pyrrol-3-yl derivatives through the reaction of arylglyoxals, malono derivatives, and different 4-amino coumarins in ethanol at reflux condition. In this method, all products were obtained in good to excellent yield. Next, all synthesized derivatives were evaluated for their α-glucosidase inhibitory activity. Most of the compounds displayed potent inhibitory activities with IC values in the range of 48.65 ± 0.01-733.83 ± 0.10 μM compared to the standard inhibitor acarbose (IC = 750.90 ± 0.14 μM). The kinetic study of compound 5e as the most potent derivative (IC = 48.65 ± 0.01 μM) showed a competitive mechanism with a K value of 42.6 µM. Moreover, docking studies revealed that dihydrochromeno[4,3-b]pyrrol-3-yl effectively interacted with important residues in the active site of α-glucosidase.

摘要

开发了一种绿色、高效的一锅多组分方法，通过在乙醇回流条件下，芳基乙二醛、丙二酸衍生物和不同的 4-氨基香豆素反应，合成了一些新型二氢色烯并[4,3-b]吡咯-3-基衍生物。在该方法中，所有产物均以良好至优异的收率获得。接下来，对所有合成的衍生物进行了α-葡萄糖苷酶抑制活性评价。与标准抑制剂阿卡波糖（IC = 750.90 ± 0.14 μM）相比，大多数化合物表现出很强的抑制活性，IC 值范围为 48.65 ± 0.01-733.83 ± 0.10 μM。作为最有效衍生物的化合物 5e 的动力学研究（IC = 48.65 ± 0.01 μM）显示出竞争性机制，K 值为 42.6 μM。此外，对接研究表明二氢色烯并[4,3-b]吡咯-3-基有效地与α-葡萄糖苷酶活性位点中的重要残基相互作用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d3e/8544188/600e652dd49c/11030_2021_10337_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d3e/8544188/3fb6aad4ad80/11030_2021_10337_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d3e/8544188/11543854a7ae/11030_2021_10337_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d3e/8544188/de086c7cce30/11030_2021_10337_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d3e/8544188/9268bb11540c/11030_2021_10337_Sch2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d3e/8544188/b0913d7a82f0/11030_2021_10337_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d3e/8544188/af8e44dde653/11030_2021_10337_Sch3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d3e/8544188/6f6980ee10f4/11030_2021_10337_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d3e/8544188/600e652dd49c/11030_2021_10337_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d3e/8544188/3fb6aad4ad80/11030_2021_10337_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d3e/8544188/11543854a7ae/11030_2021_10337_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d3e/8544188/de086c7cce30/11030_2021_10337_Sch1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d3e/8544188/9268bb11540c/11030_2021_10337_Sch2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d3e/8544188/b0913d7a82f0/11030_2021_10337_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d3e/8544188/af8e44dde653/11030_2021_10337_Sch3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d3e/8544188/6f6980ee10f4/11030_2021_10337_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3d3e/8544188/600e652dd49c/11030_2021_10337_Fig5_HTML.jpg

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