Examination of halogen substituent effects on HIV-1 integrase inhibitors derived from 2,3-dihydro-6,7-dihydroxy-1H-isoindol-1-ones and 4,5-dihydroxy-1H-isoindole-1,3(2H)-diones

Bioorg Med Chem Lett. 2009 May 15;19(10):2714-7. doi: 10.1016/j.bmcl.2009.03.122. Epub 2009 Mar 28.

Abstract

Using 2,3-dihydro-6,7-dihydroxy-1H-isoindol-1-one and 4,5-dihydroxy-1H-isoindole-1,3(2H)-dione based HIV-1 integrase inhibitors as display platforms, we undertook a thorough examination of the effects of modifying the halogen substituents on a key benzyl ring that is hypothesized to bind in a hydrophobic pocket of the integrase.DNA complex. Data from this study suggest that in general dihalo-substituted analogues have higher potency than monohalo-substituted compounds, but that further addition of halogens is not beneficial.

Publication types

  • Research Support, N.I.H., Intramural

MeSH terms

  • Cells, Cultured
  • HIV Integrase / chemistry
  • HIV Integrase / metabolism*
  • HIV Integrase Inhibitors / chemical synthesis
  • HIV Integrase Inhibitors / chemistry*
  • HIV Integrase Inhibitors / pharmacology
  • Halogens / chemical synthesis
  • Halogens / chemistry*
  • Humans
  • Isoindoles / chemical synthesis
  • Isoindoles / chemistry*
  • Isoindoles / pharmacology
  • Structure-Activity Relationship

Substances

  • HIV Integrase Inhibitors
  • Halogens
  • Isoindoles
  • HIV Integrase
  • p31 integrase protein, Human immunodeficiency virus 1