Chatterjee Sourav, Bhattacharjee Pinaki, Butterfoss Glenn L, Achari Anushree, Jaisankar Parasuraman
Laboratory of Catalysis and Chemical Biology, Department of Organic and Medicinal Chemistry, CSIR-Indian Institute of Chemical Biology 4 Raja S. C. Mullick Road Kolkata-700 032 India
Center for Genomics and Systems Biology, New York University Abu Dhabi Abu Dhabi-129188 United Arab Emirates.
RSC Adv. 2019 Jul 18;9(39):22384-22388. doi: 10.1039/c9ra05350f. eCollection 2019 Jul 17.
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.
通过围绕手性轴系统地改变官能团，在生物活性3-吲哚基呋喃类化合物中引入了轴向手性，同时牢记轴手性纯类似物可能对目标蛋白具有不同的结合亲和力和选择性。通过手性高效液相色谱分析、电子圆二色（ECD）光谱和计算建模研究了轴向手性3-吲哚基呋喃类化合物的外消旋化动力学。结果确定了光学纯3-吲哚基呋喃类化合物以稳定且可分离的阻转异构体形式存在的构型参数。
