Synthesis of Ethyl 5-Phenyl-6-Oxa-1-Azabicyclo[3.1.0]hexane-2-carboxylate Derivatives and Evaluation of Their Antimalarial Activities

Derivatives of ethyl 5-phenyl-6-oxa-1-azabicyclo[3.1.0]hexane-2-carboxylate (14−20), with side chains varying from three to five carbon atoms and bearing various substituents, have been prepared from ethyl 2-phenyl-1-pyrroline-5-carboxylate (12). Their in vitro activity against P. falciparum (K1 str...

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Bibliographic Details
Published in:	Journal of medicinal chemistry Vol. 46; no. 12; pp. 2397 - 2403
Main Authors:	Ningsanont, Nongpanga, Black, David St. C, Chanphen, Rachada, Thebtaranonth, Yodhathai
Format:	Journal Article
Language:	English
Published:	Washington, DC American Chemical Society 05-06-2003
Subjects:	Animals Antibiotics. Antiinfectious agents. Antiparasitic agents Antimalarials - chemical synthesis Antimalarials - pharmacology Antimalarials - toxicity Antiparasitic agents Antitubercular Agents - chemical synthesis Antitubercular Agents - pharmacology Antitubercular Agents - toxicity Aza Compounds - chemical synthesis Aza Compounds - pharmacology Aza Compounds - toxicity Biological and medical sciences Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis Bridged Bicyclo Compounds, Heterocyclic - pharmacology Bridged Bicyclo Compounds, Heterocyclic - toxicity Cercopithecus aethiops Chloroquine - pharmacology Drug Resistance, Multiple ethyl 2-phenyl-1-pyrroline-5-carboxylate Medical sciences Mycobacterium tuberculosis - drug effects Pharmacology. Drug treatments Plasmodium falciparum Plasmodium falciparum - drug effects Structure-Activity Relationship Vero Cells Protozoa Antimalarial Apicomplexa Cyclopropane derivatives Antiprotozoal agent Plasmodium falciparum Mycobacterium tuberculosis Structure activity relation Mycobacteriales Trans stereoisomer Parasiticid Mycobacteriaceae Bicyclic compound Bacteria Actinomycetes Antituberculous agent Chemical synthesis Oxygen nitrogen heterocycle
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Summary:	Derivatives of ethyl 5-phenyl-6-oxa-1-azabicyclo[3.1.0]hexane-2-carboxylate (14−20), with side chains varying from three to five carbon atoms and bearing various substituents, have been prepared from ethyl 2-phenyl-1-pyrroline-5-carboxylate (12). Their in vitro activity against P. falciparum (K1 strain) and antimycobacterium and also their cytotoxic activity against Vero cell have been evaluated.
Bibliography:	ark:/67375/TPS-LZHNM6N7-C istex:7963B261A8EC9C85C10CFA61DE89D138B98D327B ObjectType-Article-2 SourceType-Scholarly Journals-1 ObjectType-Feature-1 content type line 23
ISSN:	0022-2623 1520-4804
DOI:	10.1021/jm020452h