Design, synthesis and biological evaluation of substituted guanidine indole derivatives as potential inhibitors of HIV-1 Tat-TAR interaction

Med Chem. 2014;10(7):738-46. doi: 10.2174/1573406410666140306151815.

Abstract

The interaction between the HIV-1 transactivator protein Tat and RNA response element (TAR) plays a critical role in HIV-1 transcription. Based on the pharmacophore model of reported inhibitors, a series of novel substituted guanidine indole derivatives was designed, synthesized and evaluated for their in vitro HIV-1 and HIV-2 inhibitory activity using the IIIB strain and ROD strain, respectively. Preliminary biological evaluation indicated that three compounds exhibited marked inhibitory activity against HIV-1 IIIB. Quite unexpectedly, compound a-7 was also endowed with the moderate anti-HIV-2 potency (EC50 = 58.14 µM). In addition, preliminary discussion on the activity results and molecular modeling of these new analogues were presented in this manuscript.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-HIV Agents / chemical synthesis
  • Anti-HIV Agents / chemistry
  • Anti-HIV Agents / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Design*
  • Guanidine / chemical synthesis
  • Guanidine / chemistry
  • Guanidine / pharmacology*
  • HIV / drug effects
  • HIV / genetics
  • HIV / metabolism
  • Indoles / chemical synthesis
  • Indoles / chemistry
  • Indoles / pharmacology*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Protein Binding / drug effects
  • RNA, Viral / chemistry
  • RNA, Viral / metabolism*
  • Response Elements / genetics*
  • Structure-Activity Relationship
  • tat Gene Products, Human Immunodeficiency Virus / chemistry
  • tat Gene Products, Human Immunodeficiency Virus / metabolism*

Substances

  • Anti-HIV Agents
  • Indoles
  • RNA, Viral
  • tat Gene Products, Human Immunodeficiency Virus
  • Guanidine