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

Author:
Chatterjee, Sourav, Bhattacharjee, Pinaki, Butterfoss, Glenn L., Achari, Anushree, Jaisankar, Parasuraman
Source:
RSC advances 2019 v.9 no.39 pp. 22384-22388
ISSN:
2046-2069
Subject:
binding capacity, circular dichroism spectroscopy, high performance liquid chromatography, models, moieties, optical isomerism
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.
Agid:
6542941