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Related Experiment Videos

C(3)-cyclopropyl cephems and carbacephems.

D O Spry1, N J Snyder, J S Kasher

  • 1Lilly Research Laboratory, Eli Lilly & Company, Indianapolis, Indiana 46285.

The Journal of Antibiotics
|November 1, 1989
PubMed
Summary

New cyclopropyl cephem and carbacephem antibiotics were synthesized. Phenylglycyl derivatives show enhanced Gram-positive activity compared to cephalexin, but aminothiazole oxime variants were less effective.

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Area of Science:

  • Medicinal Chemistry
  • Organic Synthesis
  • Antimicrobial Agents

Background:

  • Development of novel antibiotics is crucial to combat rising antimicrobial resistance.
  • Cephem and carbacephem scaffolds are important in antibacterial drug discovery.
  • Modifications at the C(3) position can significantly impact antimicrobial activity.

Purpose of the Study:

  • To synthesize novel C(3)-cyclopropyl cephem and carbacephem derivatives.
  • To evaluate the antimicrobial activity of these new compounds, particularly against Gram-positive bacteria.
  • To compare the efficacy of C(3)-cyclopropyl derivatives with their C(3)-vinyl precursors and existing antibiotics.

Main Methods:

  • Palladium-catalyzed addition of diazomethane to C(3)-vinyl cephem and carbacephem precursors.
  • Synthesis of phenylglycyl cyclopropyl cephem derivatives.
  • Synthesis of aminothiazole oxime cyclopropyl cephem derivatives.
  • Antimicrobial activity testing against Gram-positive bacteria.

Main Results:

  • Successful synthesis of a series of C(3)-cyclopropyl cephems and carbacephems.
  • Phenylglycyl cyclopropyl cephem derivatives demonstrated superior Gram-positive activity compared to cephalexin and cefaclor.
  • Aminothiazole oxime cyclopropyl cephem derivatives showed reduced activity compared to their C(3)-vinyl counterparts.

Conclusions:

  • The C(3)-cyclopropyl modification is a viable strategy for enhancing the antibacterial potency of cephem and carbacephem scaffolds.
  • Phenylglycyl substitution at the C(3)-cyclopropyl position confers significant Gram-positive activity.
  • Further optimization is needed for aminothiazole oxime derivatives to regain comparable efficacy.

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