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Synthesis and antimalarial assessment of a new series of orally active amino-functionalized spiro 1,2,4-trioxanes.

Abstract
Keto-trioxanes 7a-d, easily accessible in two steps from allylic alcohols 5a-d, underwent reductive amination with substituted anilines to furnish amino-functionalized trioxanes 8a-i, 9a-i, 10a-i, and 11a-i. All these new trioxanes were assessed for their oral antimalarial activity against multidrug-resistant Plasmodium yoelii nigeriensis in Swiss mice. 2-Naphthalene-based trioxanes 9c and 9i, the most active compounds of the series, provided 100% protection to the malaria-infected mice at 24 mg/kg × 4 days, while the related trioxane 9b and phenanthrene-based trioxane 11e provided a similar level of protection at 48 mg/kg × 4 days. All other trioxanes, except 10c, 10d, and 10g, provided 100% protection at 96 mg/kg × 4 days. In this model, β-arteether provided 100% protection at 48 mg/kg × 4 days and 20% protection at 24 mg/kg × 4 days.
AuthorsChandan Singh, Mohammad Hassam, Niraj Krishna Naikade, Ved Prakash Verma, Ajit Shankar Singh, Sunil K Puri
JournalJournal of medicinal chemistry (J Med Chem) Vol. 53 Issue 21 Pg. 7587-98 (Nov 11 2010) ISSN: 1520-4804 [Electronic] United States
PMID20936847 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
Chemical References
  • Aniline Compounds
  • Antimalarials
  • Heterocyclic Compounds, 2-Ring
  • Ketones
  • Naphthalenes
  • Spiro Compounds
Topics
  • Administration, Oral
  • Aniline Compounds (chemical synthesis, chemistry, pharmacology)
  • Animals
  • Antimalarials (chemical synthesis, chemistry, pharmacology)
  • Drug Resistance
  • Heterocyclic Compounds, 2-Ring (chemical synthesis, chemistry, pharmacology)
  • Ketones (chemical synthesis, chemistry, pharmacology)
  • Malaria (prevention & control)
  • Mice
  • Naphthalenes (chemical synthesis, chemistry, pharmacology)
  • Parasitic Sensitivity Tests
  • Plasmodium yoelii (drug effects)
  • Spiro Compounds (chemical synthesis, chemistry, pharmacology)
  • Structure-Activity Relationship

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