Synthesis and analgesic activity of novel heterocycles, [1]benzothiopyrano[3,4-b]pyrrole derivatives.
In order to develop analgesic compounds possessing a sulfur atom in the alicyclic ring, novel cis-fused heterocycles, [1]benzothiopyrano[3,4-b]pyrrole derivatives (II) were synthesized via a unique cyclization reaction starting from 4-(4-methoxyphenylthio)-2-butanone (1) or 6-methoxy-3,4-dihydro-2H-1-benzothiopyran-4-one (7). The analgesic effects of benzothiopyranopyrroles (16, 18) were measured by means of the writhing test. The phenolic derivative 18 completely inhibited the appearance of writhing at the dose of 50 mg/kg, but the methoxy derivative 16 had no analgesic effect.
Hori
M
M
Kataoka
T
T
Shimizu
H
H
Imai
E
E
Iwata
N
N
Kawamura
N
N
Kurono
M
M
Nakano
K
K
Kido
M
M
D000700:Analgesics / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D001578:Benzopyrans / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D002839:Chromans / Q000138:chemical synthesis* / Q000494:pharmacology; D051379:Mice; D011758:Pyrroles / Q000138:chemical synthesis* / Q000494:pharmacology
D000700:Analgesics; D001578:Benzopyrans; D002839:Chromans; D011758:Pyrroles