Synthesis and antimalarial evaluation of novel benzopyrano[4,3-b]benzopyran derivatives

Ruth Devakaram; David StC Black; Katherine T Andrews; Gillian M Fisher; Rohan A Davis; Naresh Kumar

doi:10.1016/j.bmc.2011.07.009

Synthesis and antimalarial evaluation of novel benzopyrano[4,3-b]benzopyran derivatives

Bioorg Med Chem. 2011 Sep 1;19(17):5199-206. doi: 10.1016/j.bmc.2011.07.009. Epub 2011 Jul 23.

Authors

Ruth Devakaram¹, David StC Black, Katherine T Andrews, Gillian M Fisher, Rohan A Davis, Naresh Kumar

Affiliation

¹ School of Chemistry, The University of New South Wales, UNSW, NSW, Sydney, Australia.

PMID: 21824783
DOI: 10.1016/j.bmc.2011.07.009

Abstract

7-Methoxyflavenes and 5,7,8-trimethoxyflavenes were found to undergo stereoselective acid-catalyzed rearrangement to generate the benzopyrano[4,3-b]benzopyran ring system present in the natural product, dependensin. Dependensin and its analogs were subjected to antimalarial growth inhibition assays against Plasmodium falciparum and found to have IC(50) values ranging between 1.9 and 3.9 μM.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acids / chemistry
Antimalarials / chemical synthesis*
Antimalarials / chemistry
Antimalarials / pharmacology
Benzopyrans / chemical synthesis
Benzopyrans / chemistry*
Benzopyrans / pharmacology
Catalysis
Crystallography, X-Ray
Dimerization
Molecular Conformation
Plasmodium falciparum / drug effects
Stereoisomerism

Substances

Acids
Antimalarials
Benzopyrans