title: Synthesis of novel 1,2,3-triazole based benzoxazolinones: their TNF-α based molecular docking with in-vivo anti-inflammatory, antinociceptive activities and ulcerogenic risk evaluation.
abstract: A library of novel bis-heterocycles containing benzoxazolinone based 1,2,3-triazoles has been synthesized using click chemistry approach. The compound 3f exhibited potent selective COX-2 inhibition of 59.48% in comparison to standard drug celecoxib (66.36% inhibition). The compound 3i showed significant (p < 0.001, 50.95%), TNF-α inhibitory activity as compared to indomethacin (p < 0.001, 64.01%). The results of the carrageenan induced hind paw oedema showed that compounds 3a, 3f, 3i, 3o, and 3e exhibited potent anti-inflammatory activity in comparison to Indomethacin. The molecular docking studies revealed that 3i exhibits strong inhibitory effect due to the extra stability of the complex because of an extra π-π bond. The histopathology report showed that none of the compounds caused gastric ulceration.
authors.affiliation: Department of Chemistry, Faculty of Science, Jamia Hamdard (Hamdard University), New Delhi 110 062, India.
authors.forename: Saqlain
authors.initials: S
authors.lastname: Haider
authors.forename: M Sarwar
authors.initials: MS
authors.lastname: Alam
authors.forename: Hinna
authors.initials: H
authors.lastname: Hamid
authors.forename: Syed
authors.initials: S
authors.lastname: Shafi
authors.forename: Amit
authors.initials: A
authors.lastname: Nargotra
authors.forename: Priya
authors.initials: P
authors.lastname: Mahajan
authors.forename: Syed
authors.initials: S
authors.lastname: Nazreen
authors.forename: Arunasree M
authors.initials: AM
authors.lastname: Kalle
authors.forename: Chetna
authors.initials: C
authors.lastname: Kharbanda
authors.forename: Yakub
authors.initials: Y
authors.lastname: Ali
authors.forename: Aftab
authors.initials: A
authors.lastname: Alam
authors.forename: Amulya K
authors.initials: AK
authors.lastname: Panda
mesh_terms: D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000008:administration & dosage / Q000138:chemical synthesis / Q000494:pharmacology*; D001583:Benzoxazoles / Q000008:administration & dosage / Q000138:chemical synthesis / Q000494:pharmacology*; D002351:Carrageenan; D051546:Cyclooxygenase 2 / Q000378:metabolism; D052246:Cyclooxygenase 2 Inhibitors / Q000008:administration & dosage / Q000138:chemical synthesis / Q000494:pharmacology*; D004305:Dose-Response Relationship, Drug; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy*; D004847:Epithelial Cells / Q000166:cytology; D005753:Gastric Mucosa / Q000166:cytology; D006801:Humans; D008958:Models, Molecular; D015394:Molecular Structure; D051381:Rats; D012307:Risk Factors; D013329:Structure-Activity Relationship; D014230:Triazoles / Q000737:chemistry*; D014409:Tumor Necrosis Factor-alpha / Q000037:antagonists & inhibitors* / Q000378:metabolism
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D001583:Benzoxazoles; D052246:Cyclooxygenase 2 Inhibitors; D014230:Triazoles; D014409:Tumor Necrosis Factor-alpha; D002351:Carrageenan; D051546:Cyclooxygenase 2
keywords: 1,2,3-Triazole; Benzoxazolinone; Carrageenan cyclooxygenase; Click chemistry; Molecular docking