TY - JOUR
T1 - Establishment of atropisomerism in 3-indolyl furanoids
T2 - A synthetic, experimental and theoretical perspective
AU - Chatterjee, Sourav
AU - Bhattacharjee, Pinaki
AU - Butterfoss, Glenn L.
AU - Achari, Anushree
AU - Jaisankar, Parasuraman
N1 - Funding Information:
This project was funded by DST-SERB, New Delhi, India (EEQ/ 2016/000605). S. C. acknowledges UGC, New Delhi. P. B. and A. A. thankfully acknowledge CSIR, New Delhi for the award of Senior Research Fellowships. High Performance Computing resources at NYUAD was used for DFT calculations.
Funding Information:
This project was funded by DST-SERB, New Delhi, India (EEQ/2016/000605). S. C. acknowledges UGC, New Delhi. P. B. and A. A. thankfully acknowledge CSIR, New Delhi for the award of Senior Research Fellowships. High Performance Computing resources at NYUAD was used for DFT calculations.
Publisher Copyright:
© 2019 The Royal Society of Chemistry.
PY - 2019
Y1 - 2019
N2 - 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.
AB - 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.
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U2 - 10.1039/c9ra05350f
DO - 10.1039/c9ra05350f
M3 - Article
AN - SCOPUS:85069760527
SN - 2046-2069
VL - 9
SP - 22384
EP - 22388
JO - RSC Advances
JF - RSC Advances
IS - 39
ER -