Novel 3,3a,4,5,6,7-hexahydroindazole and arylthiazolylpyrazoline derivatives as anti-inflammatory agents.
A novel series of 7-benzylidene-3, 3a, 4, 5, 6, 7-hexahydro-3-phenyl-2H-indazole substituted at the 2-position were synthesized. The reaction of 2, 6-bis-benzylidenecyclohexanone (1) with thiosemicarbazide in the presence of NaOH afforded a mixture of the 3-H, 3a-H trans 2 and cis 2a diastereoisomers which have been separated by fractional recrystallization. Interaction of the first intermediate 2 with substituted phenacyl bromides, aromatic aldehydes and chloroacetic acid in presence of a mixture of acetic acid and acetic anhydride, and 2, 3-dichloroquinoxaline yielded the corresponding 7-benzylidene-3, 3a, 4, 5, 6, 7-hexahydro-3-phenyl-2H-indazole derivatives substituted at the 2-position with 4-aryl-2-thiazolyl 3a, b, 5-arylidene-4, 5-dihydro-4-oxo-2-thiazolyl 4a, b and thiazolo[4, 5-b]quinoxalin-2-yl 5, respectively. Moreover, the other intermediates 3, 5-diaryl-1-thiocarbamoyl-2-pyrazolines 7a-d were reacted with the previously-mentioned reagents and gave the corresponding 3, 5-diaryl-1-(4-aryl-2-thiazolyl)-2-pyrazolines 8a-h, 3, 5-diaryl-1-(5-arylidene-4, 5-dihydro-4-oxo-2-thiazolyl)-2-pyrazolines 9a-d and 3, 5-diaryl-1-(thiazolo[4, 5-b]quinoxalin-2-yl)-2-pyrazoline derivatives 10a, b, respectively. Some of the newly prepared compounds were subjected to evaluation for their anti-inflammatory activity. The structures of the new compounds were confirmed by elemental analyses as well as (1)H-NMR, IR, and MS data.
Nasr
Magda N A
MN
Department of Pharmacology, College of Pharmacy, University of Mansoura, Mansoura, Egypt. Magdaahnasr@yahoo.com
Said
Shehta A
SA
D000284:Administration, Oral; D000818:Animals; D002351:Carrageenan; D016861:Cyclooxygenase Inhibitors / Q000138:chemical synthesis / Q000494:pharmacology*; D004487:Edema / Q000139:chemically induced / Q000188:drug therapy; D007191:Indazoles / Q000009:adverse effects / Q000138:chemical synthesis / Q000494:pharmacology*; D008297:Male; D011720:Pyrazoles / Q000009:adverse effects / Q000138:chemical synthesis / Q000494:pharmacology*; D051381:Rats; D013329:Structure-Activity Relationship; D013678:Technology, Pharmaceutical; D013844:Thiazoles / Q000009:adverse effects / Q000138:chemical synthesis / Q000494:pharmacology*; D014456:Ulcer / Q000139:chemically induced
D016861:Cyclooxygenase Inhibitors; D007191:Indazoles; D011720:Pyrazoles; D013844:Thiazoles; D002351:Carrageenan