Synthesis of ethyl 5-phenyl-6-oxa-1-azabicyclo[3.1.0]hexane-2-carboxylate derivatives and evaluation of their antimalarial activities.

doi:10.1021/JM020452H

Paper

Synthesis of ethyl 5-phenyl-6-oxa-1-azabicyclo[3.1.0]hexane-2-carboxylate derivatives and evaluation of their antimalarial activities.

Published May 2, 2003 · Nongpanga Ningsanont, D. Black, Rachada Chanphen

Journal of medicinal chemistry

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24

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0

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Abstract

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.

Study Snapshot

Ethyl 5-phenyl-6-oxa-1-azabicyclo[3.1.0]hexane-2-carboxylate derivatives show promising antimalarial and antimycobacterial activities, with potential for further development as antimalarial drugs.

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Synthesis of ethyl 5-phenyl-6-oxa-1-azabicyclo[3.1.0]hexane-2-carboxylate derivatives and evaluation of their antimalarial activities.

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References

Citations

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Zinc-mediated reductive cyclization of 3-nitro-4-phenacylchromanes can produce fused pyrroline N-oxides, pyrrolines, and pyrrolidines in good yields without changing the pyran ring configuration.

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This study demonstrates a novel method for synthesis of 1-pyrrolines from N-alkenylnitrones and alkynes, providing high regio- and diastereoselectivity under mild conditions.

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[1+1+3] Annulation of Diazoenals and Vinyl Azides: Direct Synthesis of Functionalized 1-Pyrrolines through Olefination.

The developed rhodium-catalyzed [1+1+3] annulation reaction of diazoenals and vinyl azides allows for the direct synthesis of valuable deuterated 1-pyrrolines and structural diversification of enal-functionalized 1-pyrrolines.

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This study developed a highly chemo-, diastereo-, and enantioselective method for rapidly accessing highly functionalized 1-pyrrolines bearing two contiguous stereocenters, including a trifluoromethylated all-carbon quaternary stereocenter, in one-pot

Hypolipidemic effect of dihydroisoquinoline oxaziridine in high-fat diet-fed rats.

Oxaziridine 3 reduces body weight, inhibits lipase activity, and improves lipid profile and liver-kidney functions in high-fat diet-fed rats.

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Two new trichloromethyl substituted dihydroisoquinoline oxaziridines can be easily synthesized and show promising oxygen transfer capabilities towards sulfides in the absence of acid.