Establishment of atropisomerism in 3-indolyl furanoids: a synthetic, experimental and theoretical perspective
| Autor: | Parasuraman Jaisankar, Sourav Chatterjee, Pinaki Bhattacharjee, Glenn L. Butterfoss, Anushree Achari |
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| Rok vydání: | 2019 |
| Předmět: |
Atropisomer
Circular dichroism Stereochemistry Chemistry General Chemical Engineering Kinetics 02 engineering and technology General Chemistry 010402 general chemistry 021001 nanoscience & nanotechnology 01 natural sciences 0104 chemical sciences Stereocenter Chiral column chromatography Axial chirality 0210 nano-technology Spectroscopy Racemization |
| Zdroj: | RSC Advances. 9:22384-22388 |
| ISSN: | 2046-2069 |
| DOI: | 10.1039/c9ra05350f |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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