Design, synthesis, and biological investigation of oxadiazolyl, thiadiazolyl, and pyrimidinyl linked antipyrine derivatives as potential non-acidic anti-inflammatory agents

A novel series of 12 antipyrine derivatives containing 1,3,4-oxadiazoles (4a-d), 1,3,4-thiadiazoles (6a-d), and pyrimidines (8a-d), was preparedand assessed for its potential in vitro COX-2 inhibitors. Compared to Celecoxib, compounds 4b-d and 8d were the most potent derivatives c with a half-maxima...

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Bibliographic Details
Published inJournal of enzyme inhibition and medicinal chemistry Vol. 38; no. 1; p. 2162511
Main Authors Al-Sanea, Mohammad M., Hamdi, Abdelrahman, Brogi, Simone, S. Tawfik, Samar, Othman, Dina I. A., Elshal, Mahmoud, Ur Rahman, Hidayat, Parambi, Della G. T., M. Elbargisy, Rehab, Selim, Samy, Mostafa, Ehab M., Mohamed, Ahmed A. B.
Format Journal Article
LanguageEnglish
Published ABINGDON Taylor & Francis 01.12.2023
Taylor & Francis Ltd
Taylor & Francis Group
Subjects
anti-inflammatory
Anti-inflammatory agents
Anti-Inflammatory Agents - pharmacology
Anti-Inflammatory Agents, Non-Steroidal - pharmacology
Antipyrine
Antipyrine - pharmacology
Arthritis
Biochemistry & Molecular Biology
Celecoxib
Celecoxib - pharmacology
Chemistry
Chemistry, Medicinal
Cyclooxygenase 2 - metabolism
Cyclooxygenase 2 Inhibitors - pharmacology
Design
Drug Design
Edema - drug therapy
Enzymes
Humans
Inflammation
Investigations
Life Sciences & Biomedicine
Molecular Docking Simulation
Nonsteroidal anti-inflammatory drugs
oxadiazole
Pharmaceutical sciences
Pharmacology & Pharmacy
Pharmacy
pyrimidine
Pyrimidines
Rheumatism
Science & Technology
Structure-Activity Relationship
thiadiazole
CYCLOOXYGENASE
MOLECULAR DOCKING
DISCOVERY
PAIN
Antipyrine
oxadiazole
thiadiazole
anti-inflammatory
INHIBITORS
1,3,4-OXADIAZOLES
pyrimidine
MICROWAVE-ASSISTED SYNTHESIS
SELECTIVITY
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Summary:A novel series of 12 antipyrine derivatives containing 1,3,4-oxadiazoles (4a-d), 1,3,4-thiadiazoles (6a-d), and pyrimidines (8a-d), was preparedand assessed for its potential in vitro COX-2 inhibitors. Compared to Celecoxib, compounds 4b-d and 8d were the most potent derivatives c with a half-maximal inhibitory concentration range of 53-69 nM. Considering COX-2 selectivity index, compounds 4 b and 4c were chosen among these most potent derivatives for further investigation. The in vivo ability of compounds 4 b and 4c to counteract carrageenan-induced paw edoema has been assessed and their potential underlying mechanisms have been elucidated and the results have been further validated using molecular docking simulations.
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These authors contributed equally to this work
Supplemental data for this article can be accessed here.
ISSN:1475-6366
1475-6374
DOI:10.1080/14756366.2022.2162511