Open AccessChemical Reactivity and Skin Sensitization Studies on a Series of Chloro- and Fluoropyrroles—A Computational Approach
Author(s) -
J. Padmanabhan,
Zeeshan Arif,
Prakrity Singh,
Ramakrishnan Parthasarathi
Publication year - 2021
Publication title -
acs omega
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.779
H-Index - 40
ISSN - 2470-1343
DOI - 10.1021/acsomega.1c02436
Subject(s) - electrophile , reactivity (psychology) , skin sensitization , series (stratigraphy) , sensitization , relevance (law) , chemistry , computational chemistry , charge (physics) , biological system , computer science , computational biology , combinatorial chemistry , biology , organic chemistry , physics , neuroscience , medicine , alternative medicine , pathology , quantum mechanics , political science , law , catalysis , paleontology
Global density functional descriptors analysis on a series of chloro- and fluoropyrroles provide vital data concerning their overall biochemical activities. In this study, a comprehensive investigation is presented for a series of chloro- and fluoropyrroles using DFT-based descriptors to elucidate physicochemical properties and their relevance to reactivity, charge transfer, site selectivity, and toxicity. Electrophilicity-based charge transfer (ECT) descriptor reveals the fact that chloro- and fluoropyrroles act as electron donors during their interaction with DNA bases. The local descriptor, namely, multiphilic descriptor conveys the activeness of specific sites in chloro- and fluoropyrroles. Further, Toxicity Prediction Komputer Assisted Technology (TOPKAT) studies on carcinogenicity bioassays using four rodent models provide the interesting fact that chloro- and fluoropyrroles exhibit a strong skin sensitization effect in these species.