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Anti‐Inflammatory, Radical Scavenging Mechanism of New 4‐Aryl‐[1,3]‐thiazol‐2‐yl‐2‐quinoline Carbohydrazides and Quinolinyl[1,3]‐thiazolo[3,2‐ b ][1,2,4]triazoles
Author(s) -
Srinivasa Shashidhar Bharadwaj,
Poojary Boja,
Brahmavara Usha,
Das Anupam Jyoti,
Middha Sushil Kumar
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201801398
Subject(s) - chemistry , thiazole , antioxidant , proton nmr , quinoline , hydrogen bond , stereochemistry , medicinal chemistry , carbon 13 nmr , aryl , docking (animal) , molecule , organic chemistry , medicine , alkyl , nursing
Quinolines, thiazole and many thiazolotriazoles have been given insistence because of diversification in medicinal and biological properties associated with them. In view of these observations, it is therefore proposed to synthesize and study the biological properties of some novel quinolinylthiazolotriazole derivatives. All derivatives were characterized by FTIR, 1 H NMR, 13 C NMR and mass spectra. All compounds 5 a–g and 7 a–g series were screened for antioxidant and anti‐inflammatory potential. In 5 a‐g series, compounds 5 c (4‐NO 2 ) and 5 a (4‐Br) derivatives showed free radical scavenging activity with IC 50 values of 425.9 μg/ml and 413.3 μg/ml. In 7 a‐g series, compound 7 c (3‐NO 2 ) and 7 g (4‐OH) derivatives showed highest free radical scavenging activity with IC 50 values 7.75 μg/ml and 14.06 μg/ml. Compounds 5 a, 5 c, 7 c and 7 g exhibited pronounced anti‐inflammatory activity among all other synthesized compounds. Molecular docking studies revealed good binding through hydrogen bonding with catalytic residues as well as neighboring residues at the active site of target protein trypsin. Among all the synthesized compounds 5 c, 5 a, 7 c and 7 g showed least binding energy values of −10.70 kcal/mol, −9.69 kcal/mol, −11.47 kcal/mol and −9.83 kcal/mol respectively. Results from antioxidant, anti‐inflammatory and in silico studies suggest that the synthesized compounds may be potential antioxidant and anti‐inflammatory agents and can act as lead molecules in drug discovery.