Plasmodium Falciparum: Role of Absolute Stereochemistry in the Antimalarial Activity of Synthetic Amino Alcohol Antimalarial Agents

Abstract

The (+)-isomers of mefloquine and its threo analog are 1.69 to 1.95 times more active than the (-)-isomers against chloroquine-sensitive and chloroquine-resistant Plasmodium falciparum in vitro. This large a differential between the activity of (+)- and (-)-isomers was not observed for other synthetic amino alcohol anti agents containing a piperidine ring. The enantiomers of amino-alcohol antimalarial agents in which the amine is part of an acrylic group, such as in halofantrine, displayed little, if any, differential antimalarial activity. Thus, the effect of absolute stereochemistry of the amino alcohol antimalarial agents on antimalarial activity appears to depend upon both the flexibility of the amine portion of the molecule and the structure of the aromatic portion of the molecule.

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Document Details

Document Type
Technical Report
Publication Date
Jan 01, 1993
Accession Number
ADA269099

Entities

People

  • J. M. Karle
  • L. Gerena
  • R. Olmeda
  • W. K. Milhous

Organizations

  • Walter Reed Army Institute of Research

Tags

DTIC Thesaurus Topics

  • Alcohols
  • Alkaloids
  • Anti-Infective Agents
  • Antimalarials
  • Chemical Synthesis
  • Chemistry
  • Chemotherapy
  • Crystal Structure
  • Isomers
  • Liquid Chromatography
  • Malaria
  • Molecules
  • Organic Chemistry
  • Parasitology
  • Particle Size
  • Pharmacology
  • Statistical Analysis

Fields of Study

  • Chemistry
  • Medicine

Readers

  • Organic Chemistry
  • Parasitology and Pharmacology of Malaria.