[Synthesis and antinociceptive activity of seselin derivatives].
Natural product seselin and related derivatives with an angular pyranocoumarin skeleton were synthesized from 8-acetyl-7-hydroxycoumarins by condensation with acetone, reduction, and dehydration successively under mild conditions with total yield of > 50%. Twelve seselin derivatives were tested by the writhing response assay induced by acetic acid at a dose of 40 mg x kg(-1). Seselin (4a) and 4,8,8-trimethyl-9,9-dihydro-pyran[2,3-f] chromene-2,10-dione (2b) showed obviously antinociceptive activity with inhibitory effect of 85% and 50%, respectively, more or quite potent than aspirin in the same assay, suggesting that seselin derivatives could be a novel kind of potential antinociceptive agents.
Guo
Huan-fang
HF
Beijing Institute of Pharmacology and Toxicology, Beijing 100850, China.
Zhou
Pei-lan
PL
Gong
Ze-hui
ZH
Xie
Lan
L
D000700:Analgesics / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D002867:Chromones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D003374:Coumarins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005260:Female; D008297:Male; D051379:Mice; D015394:Molecular Structure; D010147:Pain Measurement / Q000187:drug effects
C544005:4,8,8-trimethyl-9,9-dihydropyran(2,3-f)chromene-2,10-dione; D000700:Analgesics; D002867:Chromones; D003374:Coumarins; C516746:seselin