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Synthesis, anti‐inflammatory activity, and molecular docking studies of some novel Mannich bases of the 1,3,4‐oxadiazole‐2(3 H )‐thione scaffold
Author(s) -
Ozyazici Tugce,
Gurdal Enise E.,
Orak Duygu,
Sipahi Hande,
Ercetin Tuba,
Gulcan Hayrettin O.,
Koksal Meric
Publication year - 2020
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.202000061
Subject(s) - chemistry , oxadiazole , ibuprofen , docking (animal) , stereochemistry , carbon 13 nmr , cyclooxygenase , nitric oxide , salicylic acid , enzyme , combinatorial chemistry , pharmacology , biochemistry , organic chemistry , medicine , nursing
A series of novel ibuprofen and salicylic acid‐based 3,5‐disubstituted‐1,3,4‐oxadiazole‐2(3 H )‐thione derivatives was synthesized, and they were evaluated as potential anti‐inflammatory agents. Following the structure identification studies employing IR, 1 H nuclear magnetic resonance (NMR), 13 C NMR, and elemental analysis, the title compounds were tested by cyclooxygenase (COX)‐1 and COX‐2 inhibition assays concomitant to lipopolysaccharide (LPS)‐induced nitric oxide and prostaglandin production prevention experiments. The results indicated that the majority of the compounds displayed either a superior or comparable activity in preventing both LPS‐induced NO production and COX‐1 activity in comparison to the activities of the reference molecules. Furthermore, docking studies were also performed to reveal possible interactions with the COX enzymes.