Synthesis of novel spiropyrrolizidines as potent antimicrobial agents for human and plant pathogens

Bioorg Med Chem Lett. 2008 Apr 1;18(7):2342-5. doi: 10.1016/j.bmcl.2008.02.065. Epub 2008 Mar 4.

Abstract

A series of novel dispirooxindolopyrrolizidine derivatives have been synthesized through 1,3-dipolar cycloaddition reaction of azomethine ylide generated from proline and isatin with the dipolarophile (E)-2-arylidine-1-keto carbazoles. The synthesized cycloadducts were evaluated for antimicrobial activities. Compounds 7d and 7e showed relatively good antibacterial and antifungal activities.

MeSH terms

  • Anti-Infective Agents / chemical synthesis
  • Anti-Infective Agents / pharmacology*
  • Aziridines / chemistry
  • Azo Compounds / chemistry
  • Bacteria / drug effects*
  • Carbazoles
  • Cyclization
  • Fungi / drug effects*
  • Humans
  • Isatin / chemistry
  • Microbial Sensitivity Tests
  • Models, Chemical
  • Plants / drug effects*
  • Plants / microbiology
  • Proline / chemistry
  • Pyrrolizidine Alkaloids / chemical synthesis
  • Pyrrolizidine Alkaloids / pharmacology*
  • Spiro Compounds / chemical synthesis
  • Spiro Compounds / pharmacology*
  • Thiosemicarbazones / chemistry

Substances

  • Anti-Infective Agents
  • Aziridines
  • Azo Compounds
  • Carbazoles
  • Pyrrolizidine Alkaloids
  • Spiro Compounds
  • Thiosemicarbazones
  • azomethine
  • Isatin
  • Proline