[Study of asymmetrically substituted myo-inositols. XXXIX. The synthesis of conjugate of 2',3'-didehydro-3'-dehydroxythymidine with phosphatidylinositol: a new nucleoside phospholipid with potential anti-HIV activity]

Bioorg Khim. 2003 May-Jun;29(3):296-302. doi: 10.1023/a:1023988500659.
[Article in Russian]

Abstract

A partially protected phosphatidylinositol with a free hydroxyl group in the cyclitol moiety was synthesized by phosphorylation of a tetrasubstituted myo-inositol using the H-phosphonate and phosphoamidite methods. The H-phosphonate method was advantageous for the synthesis of selectively protected monophosphoinositide due to a lesser number of stages. Two schemes for the conjugation of 2',3'-didehydro-3'-dehydroxythymidine with phosphatidylinositol using succinic acid as a linker were tested in the synthesis of the target nucleoside phospholipid.

Publication types

  • English Abstract

MeSH terms

  • Anti-HIV Agents / chemical synthesis*
  • Anti-HIV Agents / pharmacology
  • Chemistry, Organic / methods*
  • Inositol / analogs & derivatives*
  • Inositol / chemistry*
  • Magnetic Resonance Spectroscopy
  • Molecular Structure
  • Phosphatidylinositols / chemical synthesis*
  • Phosphatidylinositols / chemistry*
  • Phosphatidylinositols / pharmacology
  • Phospholipids / chemistry
  • Phosphorylation
  • Succinic Acid / chemistry
  • Thymidine / analogs & derivatives
  • Thymidine / chemical synthesis*
  • Thymidine / chemistry*
  • Thymidine / pharmacology

Substances

  • 2',3'-didehydro-5'-(3-((1,2-dipalmitoylphosphatidylinositol-4-yl)carbonyl)propanoyl)thymidine
  • Anti-HIV Agents
  • Phosphatidylinositols
  • Phospholipids
  • Inositol
  • Succinic Acid
  • Thymidine