CCR5 antagonists as anti-HIV-1 agents. Part 2: Synthesis and biological evaluation of N-[3-(4-benzylpiperidin-1-yl)propyl]-N,N'-diphenylureas

Bioorg Med Chem. 2004 May 1;12(9):2295-306. doi: 10.1016/j.bmc.2004.02.004.

Abstract

We have previously reported the novel lead compound 1a as a CCR5 antagonist for treatment of HIV-1 infection. SAR studies on incorporating various acyl groups as a replacement for the 5-oxopyrrolidine-3-carbonyl group of the lead structure resulted in the discovery of N-[3-(4-benzylpiperidin-1-yl)propyl]-N,N'-diphenylurea (4a) with significantly improved CCR5 binding affinity. Substitutions (4-Cl, 4e,f; 4-Me, 4i) on the N'-phenyl ring further increased the binding affinity. Introduction of polar substituents on the phenyl ring of the 4-benzylpiperidine moiety enhanced the inhibitory activity of the HIV-1 envelope-mediated membrane fusion (4v,w), suggesting that polar substituents at this position can interfere effectively with HIV-1 cell entry.

MeSH terms

  • Animals
  • Anti-HIV Agents / chemical synthesis*
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / pharmacology*
  • CCR5 Receptor Antagonists*
  • CHO Cells
  • Carbanilides / chemical synthesis*
  • Carbanilides / chemistry
  • Carbanilides / pharmacology*
  • Cricetinae
  • HIV-1 / drug effects
  • HIV-1 / physiology
  • Magnetic Resonance Spectroscopy
  • Membrane Fusion / drug effects

Substances

  • Anti-HIV Agents
  • CCR5 Receptor Antagonists
  • Carbanilides