Establishment of atropisomerism in 3-indolyl furanoids: A synthetic, experimental and theoretical perspective

Sourav Chatterjee, Pinaki Bhattacharjee, Glenn Butterfoss, Anushree Achari, Parasuraman Jaisankar

Research output: Contribution to journalArticle

Abstract

Introduction of axial chirality in bioactive 3-indolyl furanoids has been achieved by systematic alteration of functional groups around the stereogenic axis, keeping in mind that atropisomerically pure analogues may possess different binding affinities and selectivities towards a target protein. The kinetics of racemization of axially chiral 3-indolyl furanoids have been studied through chiral HPLC analysis, electronic circular dichroism (ECD) spectroscopy, and computational modeling. The results identify the configurational parameters for optically pure 3-indolyl furanoids to exist as stable and isolable atropisomeric form.

Original languageEnglish (US)
Pages (from-to)22384-22388
Number of pages5
JournalRSC Advances
Volume9
Issue number39
DOIs
Publication statusPublished - Jan 1 2019

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ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

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