Synthesis and antimicrobial activity of highly functionalised novel β-lactam grafted spiropyrrolidines and pyrrolizidines

Eur J Med Chem. 2011 Feb;46(2):600-7. doi: 10.1016/j.ejmech.2010.11.039. Epub 2010 Dec 1.

Abstract

A facile and one-pot synthesis of a series of novel spiropyrrolidines/pyrrolizidines with β-lactam substituent has been accomplished through 1,3-dipolar cycloaddition reaction of alkenyl esters derived from β-lactam aldehyde as dipolarophile with the dipole azomethine ylide derived from 1,2- and 1,3-diketones and secondary amino acids. The synthesized compounds were evaluated for antimicrobial activities and found to exhibit relatively good antibacterial activity at lower concentration against four human bacterial pathogens.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Crystallography, X-Ray
  • Microbial Sensitivity Tests
  • Models, Molecular
  • Molecular Conformation
  • Proteus mirabilis / drug effects
  • Proteus vulgaris / drug effects
  • Pyrrolidines / chemical synthesis
  • Pyrrolidines / chemistry
  • Pyrrolidines / pharmacology*
  • Pyrrolizidine Alkaloids / chemical synthesis
  • Pyrrolizidine Alkaloids / chemistry
  • Pyrrolizidine Alkaloids / pharmacology*
  • Salmonella typhi / drug effects
  • Spiro Compounds / chemical synthesis
  • Spiro Compounds / chemistry
  • Spiro Compounds / pharmacology*
  • Staphylococcus aureus / drug effects
  • Stereoisomerism
  • Structure-Activity Relationship
  • beta-Lactams / chemical synthesis
  • beta-Lactams / chemistry
  • beta-Lactams / pharmacology*

Substances

  • Anti-Bacterial Agents
  • Pyrrolidines
  • Pyrrolizidine Alkaloids
  • Spiro Compounds
  • beta-Lactams