[Thiophene as a structural element of physiologically active compounds. 19. The synthesis of substituted (6H-thieno[2,3-b]pyrrol-4-yl)phenylmethanones].
The synthesis of 4-Methoxyphenyl-[5-methyl-6-(2-(4-morpholinyl)-ethyl)-6H-thieno[2,3- b]pyrrol-4-yl)phenylmethanone (1), a thiophene analogue of the analgesic Pravadoline B, is described. Starting with the acetylprotected thienylhydrazine 2b compound 7 was obtained in a Fischer-analogue cyclication in two steps. Use of the BOC-protected thienylhydrazine 2a yielded the pyrazol 5. Alkylation of 7 with N-(2-Chloroethyl)morpholine gave the target compound 1. In the acetylcholine-writhing-test in mice as well as in the acetic acid-writhing-test in rats 1 showed a significant lower antinociceptive activity than Pravadolin (B).
Binder
D
D
Institut für Organische Chemie der Technischen Universität, Wien.
Schnait
H
H
Rovenszky
F
F
Enzenhofer
R
R
Stroissnig
H
H
D000700:Analgesics / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D007211:Indoles / Q000494:pharmacology; D051379:Mice; D009020:Morphine / Q000494:pharmacology; D009025:Morpholines / Q000138:chemical synthesis* / Q000494:pharmacology; D010146:Pain / Q000139:chemically induced / Q000517:prevention & control; D051381:Rats; D013876:Thiophenes / Q000138:chemical synthesis* / Q000494:pharmacology
D000700:Analgesics; D007211:Indoles; D009025:Morpholines; D013876:Thiophenes; C070126:4-methoxyphenyl-(5-methyl-6-(2-(4-morpholinyl)ethyl)-6H-thieno(2,3-b)pyrrol-4-yl)phenylmethanone; D009020:Morphine; C062767:pravadoline
Thiophen als Strukturelement physiologisch aktiver Substanzen, 19. Mitt. Die Synthese von substituierten (6H-Thieno[2,3-b]pyrrol-4-yl)-phenylmethanonen.