Catalytic asymmetric synthesis of indole derivatives as novel α-glucosidase inhibitors in vitro

Mohammad Shahidul Islam, Assem Barakat, Abdullah Mohammed Al-Majid, M. Ali, Sammer Yousuf, M. Iqbal Choudhary, Ruqaiya Khalil, Zaheer Ul-Haq

Research output: Contribution to journalJournal articlepeer-review

16 Scopus citations

Abstract

Indole containing compounds have acquired conspicuous significance due to their wide spectrum of biological activities. Synthesis of a series of enantiomerically pure indole derivatives 3a-r via Friedel–Crafts alkylation of indole 1 with enones 2a-r were described here. The products were isolated in a moderate to excellent yields (upto 89%) with excellent enantioselectivities (upto 99.9% ee). These compounds 3a-r were evaluated for their in vitro α-glucosidase inhibitory activity and some of them were identified as potent inhibitors (IC 50 = 4.3 ± 0.13–43.9 ± 0.51 μM) with several fold higher activity than the clinically used α-glucosidase inhibitor, acarbose (IC 50 = 840 ± 1.73 μM). To the best of knowledge, this is the first report of the propanone substituted indole ring containing compounds by in vitro α-glucosidase enzyme inhibition.

Original languageEnglish
Pages (from-to)350-354
Number of pages5
JournalBioorganic Chemistry
Volume79
DOIs
StatePublished - Sep 2018
Externally publishedYes

Keywords

  • Friedel–Crafts alkylation
  • Indole derivatives
  • Molecular docking
  • α-Glucosidase inhibitor

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