Structure-activity relationships in platelet-activating factor (PAF). 10. From PAF antagonism to inhibition of HIV-1 replication

J Med Chem. 2000 Jun 1;43(11):2149-54. doi: 10.1021/jm9911276.

Abstract

Excessive levels of PAF and cells of macrophage lineage appear to play an important role in neuronal cell injury, inflammatory syndrome, and HIV replication in CNS resulting in AIDS dementia complex (ADC). The beneficial effects of PAF receptor antagonists are evident and give rise to expected therapeutic strategies for neurotrauma. Piperazine derivatives bearing a "cache-oreilles" (ear-muff) electronic distribution are able to inhibit in vitro PAF effects and, thus, could be used in pathologies where this mediator is involved. Therefore, their potential anti-HIV activity was investigated, and we find that (i) these PAF antagonists are effectively active in HIV-infected monocyte-derived macrophages (MDM) but there is no correlation between both anti-HIV and anti-PAF activities; (ii) the presence of a carbamate function (compounds 1a-d) is favorable to the antiviral activity; (iii) the lipophilicity of the substituent on the piperazinic cycle seems to be less important for the anti-PAF activity than for the antiviral one. Our leading compound, PMS 601 (compound 1a), presents a dual activity with IC(50) of 8 and 11 microM for anti-PAF and anti-HIV activity, respectively, without cytotoxic events at 1000 microM in MDM. Although its mode of action is not clearly defined, these data suggest that PMS 601, which displays no effect on acellular reverse transcriptase or protease tests, deserves further investigation in the treatment of HIV-1-associated dementia.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / pharmacology*
  • Cells, Cultured
  • HIV / drug effects*
  • HIV / physiology
  • Humans
  • In Vitro Techniques
  • Inhibitory Concentration 50
  • Macrophages / drug effects
  • Macrophages / virology
  • Microbial Sensitivity Tests
  • Piperazines / chemical synthesis
  • Piperazines / chemistry
  • Piperazines / pharmacology*
  • Platelet Activating Factor / antagonists & inhibitors*
  • Platelet Membrane Glycoproteins / antagonists & inhibitors*
  • Pyridines / pharmacology
  • Receptors, Cell Surface*
  • Receptors, G-Protein-Coupled*
  • Structure-Activity Relationship
  • Thiazoles / pharmacology
  • Virus Replication / drug effects

Substances

  • Anti-HIV Agents
  • PMS 601
  • Piperazines
  • Platelet Activating Factor
  • Platelet Membrane Glycoproteins
  • Pyridines
  • Receptors, Cell Surface
  • Receptors, G-Protein-Coupled
  • Thiazoles
  • platelet activating factor receptor
  • 3-(3-pyridinyl)-1H,3H-pyrrolo(1,2-c)thiazole-7-carboxamide