Studies on chemical modification of monensin. V. Synthesis, sodium ion permeability, antibacterial activity, and crystal structure of 7-O-(4-substituted benzyl)monensins

Chem Pharm Bull (Tokyo). 1994 Nov;42(11):2269-75. doi: 10.1248/cpb.42.2269.

Abstract

7-O-(4-Substituted benzyl)monensins (3a-g) were synthesized from monensin (1), and their lipophilicity, antibacterial activity, and Na+ ion permeability were examined. 7-O-(4-Ethylbenzyl)monensin (3e) showed the largest Na+ ion permeability, but 3c,f,g showed smaller Na+ ion permeability than 7-O-benzylmonensin (2) in spite of higher lipophilicity. An X-ray study of the sodium salt of 3e revealed that the benzyl group was located over the position between the D and E rings, and that the ethyl substituent on the benzyl group was close to the C(28) methyl group on the E ring.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemistry*
  • Anti-Bacterial Agents / pharmacology*
  • Cell Membrane Permeability / drug effects*
  • Crystallography, X-Ray
  • Erythrocyte Membrane / drug effects*
  • Erythrocyte Membrane / metabolism*
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Monensin / analogs & derivatives*
  • Monensin / chemistry
  • Monensin / pharmacology*
  • Sodium / pharmacokinetics*

Substances

  • Anti-Bacterial Agents
  • Monensin
  • Sodium