[Thiophene as a structural element of physiologically active compounds. 19. The synthesis of substituted (6H-thieno[2,3-b]pyrrol-4-yl)phenylmethanones]

Arch Pharm (Weinheim). 1991 Apr;324(4):219-21. doi: 10.1002/ardp.19913240406.
[Article in German]

Abstract

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).

Publication types

  • English Abstract

MeSH terms

  • Analgesics / chemical synthesis*
  • Analgesics / pharmacology
  • Animals
  • Indoles / pharmacology
  • Mice
  • Morphine / pharmacology
  • Morpholines / chemical synthesis*
  • Morpholines / pharmacology
  • Pain / chemically induced
  • Pain / prevention & control
  • Rats
  • Thiophenes / chemical synthesis*
  • Thiophenes / pharmacology

Substances

  • Analgesics
  • Indoles
  • Morpholines
  • Thiophenes
  • 4-methoxyphenyl-(5-methyl-6-(2-(4-morpholinyl)ethyl)-6H-thieno(2,3-b)pyrrol-4-yl)phenylmethanone
  • Morphine
  • pravadoline