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Mimicking the intramolecular hydrogen bond: Synthesis, biological evaluation, and molecular modeling of benzoxazines and quinazolines as potential antimalarial agents

Gemma, Sandra; Camodeca, Caterina; Brindisi, Margherita; Brogi, Simone; Kukreja, Gagan; Kunjir, Sanil; Gabellieri, Emanuele; Lucantoni, Leonardo; Habluetzel, Annette; Taramelli, Donatella; Martin, Rowena; Summers, Robert


The intramolecular hydrogen bond formed between a protonated amine and a neighboring H-bond acceptor group in the side chain of amodiaquine and isoquine is thought to play an important role in their antimalarial activities. Here we describe isoquine-based compounds in which the intramolecular H-bond is mimicked by a methylene linker. The antimalarial activities of the resulting benzoxazines, their isosteric tetrahydroquinazoline derivatives, and febrifugine-based 1,3-quinazolin-4-ones were...[Show more]

CollectionsANU Research Publications
Date published: 2012
Type: Journal article
Source: Journal of Medicinal Chemistry
DOI: 10.1021/jm300831b


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