Novel protection-deprotection strategies in diazeniumdiolate chemistry: synthesis of V-IPA/NO

Chem Commun (Camb). 2011 Jun 21;47(23):6710-2. doi: 10.1039/c1cc12130h. Epub 2011 May 10.

Abstract

Synthesis of previously inaccessible, potentially liver selective HNO donor V-IPA/NO ([iPrHN(3)-N(1)(O(1))=N(2)-O(2)-R], where R = vinyl) is reported here. A novel fluoride-labile TOM group at O-2 in conjunction with MOM protection at N-3 in IPA/NO is employed. The strategy developed is also extended to synthesis of other NO-releasing prodrugs and has applications in diversity-oriented synthesis of HNO- and NO-prodrugs.

Publication types

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

MeSH terms

  • Azo Compounds / chemistry*
  • Cytochrome P-450 Enzyme System / chemistry
  • Cytochrome P-450 Enzyme System / metabolism
  • Nitric Oxide / chemistry
  • Nitrogen Oxides / chemistry
  • Prodrugs / chemical synthesis
  • Prodrugs / chemistry
  • Vinyl Compounds / chemical synthesis*
  • Vinyl Compounds / chemistry

Substances

  • Azo Compounds
  • Nitrogen Oxides
  • Prodrugs
  • Vinyl Compounds
  • diazeniumdiolate
  • Nitric Oxide
  • Cytochrome P-450 Enzyme System
  • nitroxyl