title: 3-substituted piperazinomethyl benzoxazolinones. Analgesic and anti-inflammatory compounds inhibiting prostaglandin E2.
abstract: Fourty-three new benzoxazolinone derivatives having a piperazinomethyl group at the third position of the ring were synthesized by using appropriate benzoxazolinones and 4-substituted piperazines via a Mannich reaction. The structures of the compounds were elucidated by spectral data and microanalyses. Analgesic activities were evaluated by a modified Koster test. All compounds, except 7, 14, 21, 32, and 41, showed analgesic activity higher than that of acetylsalicylic acid. The compounds were also screened for their anti-inflammatory activity using a carrageenan paw edema test, and those exhibiting high anti-inflammatory activity were investigated for their ability to inhibit prostaglandin E2 induced paw edema. The results of anti-inflammatory testing indicated that most of the compounds were more active than indometacin. Ulcerogenic activities of the compounds were also studied and no gastrointestinal bleeding was observed at the 100 mg/kg dose level.
authors.affiliation: Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Hacettepe University, Ankara, Turkey.
authors.forename: E
authors.initials: E
authors.lastname: Palaska
authors.forename: S
authors.initials: S
authors.lastname: Unlü
authors.forename: F
authors.initials: F
authors.lastname: Ozkanli
authors.forename: G
authors.initials: G
authors.lastname: Pilli
authors.forename: H
authors.initials: H
authors.lastname: Erdoğan
authors.forename: C
authors.initials: C
authors.lastname: Safak
authors.forename: R
authors.initials: R
authors.lastname: Demirdamar
authors.forename: B
authors.initials: B
authors.lastname: Gümüşel
authors.forename: S
authors.initials: S
authors.lastname: Duru
mesh_terms: D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D001241:Aspirin / Q000494:pharmacology; D001583:Benzoxazoles / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D002351:Carrageenan; D004487:Edema / Q000139:chemically induced / Q000517:prevention & control; D005260:Female; D008352:Mannich Bases / Q000737:chemistry; D051379:Mice; D010879:Piperazines / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D011448:Prostaglandin Antagonists / Q000138:chemical synthesis* / Q000494:pharmacology / Q000633:toxicity; D013276:Stomach Ulcer / Q000139:chemically induced
chemical_list: D000894:Anti-Inflammatory Agents, Non-Steroidal; D001583:Benzoxazoles; D008352:Mannich Bases; D010879:Piperazines; D011448:Prostaglandin Antagonists; D002351:Carrageenan; D001241:Aspirin