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Issue 39, 2019
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Establishment of atropisomerism in 3-indolyl furanoids: a synthetic, experimental and theoretical perspective

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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.

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

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Supplementary files

Article information


Submitted
12 Jul 2019
Accepted
15 Jul 2019
First published
18 Jul 2019

This article is Open Access

RSC Adv., 2019,9, 22384-22388
Article type
Paper

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

S. Chatterjee, P. Bhattacharjee, G. L. Butterfoss, A. Achari and P. Jaisankar, RSC Adv., 2019, 9, 22384
DOI: 10.1039/C9RA05350F

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