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Towards the Synthesis of Imidazopyridine Derivatives: Characterization, Single Crystal XRD, Hirshfeld Analysis, and Biological Evaluation
Author(s) -
Kuthyala Sharanya,
Sheikh Sareen,
Nagaraja G. K.,
Kannika B. R.,
Madan Kumar S.,
Chandra Nayak S.,
Lokanath N. K.
Publication year - 2021
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202003632
Subject(s) - imidazopyridine , monoclinic crystal system , chemistry , pyridine , crystal structure , pyrazine , stereochemistry , acetamide , crystallography , medicinal chemistry , organic chemistry
This study explores the synthesis of different imidazopyridine derivatives, their characterization, single crystal x‐ray diffraction, molecular Hirshfeld surface analysis along with their anticancer and other supportive biological evaluations. X‐ray crystallography study resolved the crystal structure of 2,7‐dimethyl‐N‐(1,3‐dioxoisoindolin‐2‐yl) H ‐imidazo[1,2‐ a ]pyridine‐3‐carboxamide ( 2 a ) as monoclinic crystal system (space group P2 1 /n). Graphical tool, Hirshfeld surface analysis quantified the major contribution of H⋅⋅⋅H, O⋅⋅⋅H, and C⋅⋅⋅H interactions towards the HS. Among the synthesized compounds, 2‐(4‐(4‐fluorophenyl)‐5‐(2,8‐dimethyl H ‐imidazo[1,2‐ a ]pyridin‐3‐yl)‐4 H ‐1,2,4‐triazol‐3‐ylthio)‐N‐(4‐fluorophenyl)acetamide ( 5 a ) exhibited the highest cytotoxicity against lung adenocarcinoma with IC 50 value of 43.04 μM. Selective action of 5 a was assured by cell death analysis using AO‐EB assay. In addition, the study was also supported by molecular docking studies. Together the study revealed, the compound 5 a , to be a likely candidate for further exploratory study in cancer treatment.