Novel 3,6-disubstituted 7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazines: synthesis, characterization, and evaluation of analgesic/anti-inflammatory, antioxidant activities.
In this study, the synthesis of a new series of 3,6-disubstituted-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazine 1a-4c compounds derived from 4-amino-3-substituted-1,2,4-triazole-5-thiones 1-4 is described. All of the synthesized compounds were screened for their possible analgesic / anti-inflammatory, antioxidant activities and gastric toxicity. The compound 2c was found to have both significant analgesic and consistent anti-inflammatory activity without inducing any gastric lesions along with minimal lipid peroxidation. A deep insight into the structures of the active compounds revealed that the compounds carrying an electron withdrawing group (a chloride or fluoride) on the phenyl ring at 6-position of the condensed heterocyclic derivatives exhibited noticeable higher activity.
Hacettepe University, Faculty of Pharmacy, Department of Pharmaceutical Chemistry, Sihhiye, Ankara, Turkey. tbirsen@hacettepe.edu.tr
Birsen
B
Tozkoparan
Sevim Peri
SP
Aytaç
Göknur
G
Aktay
D019342:Acetic Acid; D000700:Analgesics / Q000138:chemical synthesis / Q000494:pharmacology*; D000818:Animals; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis / Q000494:pharmacology*; D000975:Antioxidants / Q000138:chemical synthesis / Q000494:pharmacology*; D002351:Carrageenan; D004353:Drug Evaluation, Preclinical; D004487:Edema / Q000139:chemically induced / Q000517:prevention & control; D005260:Female; D015227:Lipid Peroxidation; D009682:Magnetic Resonance Spectroscopy; D008297:Male; D051379:Mice; D008807:Mice, Inbred BALB C; D013055:Spectrophotometry, Infrared; D013276:Stomach Ulcer / Q000139:chemically induced / Q000517:prevention & control; D013329:Structure-Activity Relationship; D013829:Thiadiazines / Q000138:chemical synthesis / Q000494:pharmacology*; D014230:Triazoles / Q000138:chemical synthesis / Q000494:pharmacology*
D000700:Analgesics; D000894:Anti-Inflammatory Agents, Non-Steroidal; D000975:Antioxidants; D013829:Thiadiazines; D014230:Triazoles; D002351:Carrageenan; D019342:Acetic Acid