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SteroidsVolume 61, Issue 12, December 1996, Pages 688-696

Steroidal geminal dihydroperoxides and 1,2,4,5-tetraoxanes: Structure determination and their antimalarial activity(Article)

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  • aInst. of Chemistry, Technol. and M., Belgrade, Serbia
  • bLab. de Chim. Phys. et de C., Univ. Catholique de Louvain, Louvain-la-Neuve, Belgium
  • cFLOW Inc., Portland, OR, Serbia
  • dFaculty of Chemistry, University of Belgrade, Belgrade, Serbia
  • eFaculty of Chemistry, University of Belgrade, Studentski trg 16, YU-11001, Belgrade, Serbia

Abstract

Cholestane-derived gem-dihydroperoxides and tetraoxanes were synthesized starting from 5α- and 5β-cholestan-3-ones by acid-catalyzed addition of hydrogen peroxide to the ketone. They were characterized by IR, NMR, and mass spectroscopy analysis aided by molecular mechanics calculations, and, in the instance of 5β-cholestane-3α,3β-dihydroperoxide (6), by x-ray analysis. The synthesized compounds were tested in vitro against Plasmodium falciparum Sierra Leone (D6) and Indochina (WZ) malaria clones. All compounds were inactive to both clones, with the exception of tetraoxane 7a, which exhibited modest activity toward D6 clone with IC50 = 155 nM.

Author keywords

antimalarial activitygem-dihydroperoxidemolecular mechanicsperoxidetetraoxane

Indexed keywords

EMTREE drug terms:1,2,4,5 tetraoxane derivativeantimalarial agentbis(3 dioxy 5alpha cholestane)hydroperoxide derivativeunclassified drug
EMTREE medical terms:antimalarial activityarticlechemical structuredrug synthesisinfrared spectroscopymalariamass spectrometryPlasmodium falciparumproton nuclear magnetic resonance
  • ISSN: 0039128X
  • CODEN: STEDA
  • Source Type: Journal
  • Original language: English
  • DOI: 10.1016/S0039-128X(96)00203-6
  • PubMed ID: 8987137
  • Document Type: Article
  • Publisher: Elsevier Inc.

  Solaja, B.A.; Faculty of Chemistry, University of Belgrade, PO Box 158, Serbia
© Copyright 2019 Elsevier B.V., All rights reserved.

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