Synthesis and antimalarial activity of quinones and structurally-related oxirane derivatives

Carneiro, Paula Fernandes; Pinto, Maria do Carmo Freire Ribeiro; Marra, Roberta Katlen Fusco; Silva, F. C. da; Resende, Jackson Antonio Lamounier Carmargos; Silva, Luiz Francisco Rocha e; Alves, Hilkem G.; Barbosa, Gleyce dos Santos; Vasconcellos, Marne Carvalho de; Lima, Emerson Silva; Pohlit, Adrian Martin; Ferreira, V?tor Francisco

Use este identificador para citar ou linkar para este item: https://repositorio.inpa.gov.br/handle/1/17380

Título:	Synthesis and antimalarial activity of quinones and structurally-related oxirane derivatives
Autor:	Carneiro, Paula Fernandes Pinto, Maria do Carmo Freire Ribeiro Marra, Roberta Katlen Fusco Silva, F. C. da Resende, Jackson Antonio Lamounier Carmargos Silva, Luiz Francisco Rocha e Alves, Hilkem G. Barbosa, Gleyce dos Santos Vasconcellos, Marne Carvalho de Lima, Emerson Silva Pohlit, Adrian Martin Ferreira, V?tor Francisco
Palavras-chave:	2 (allyloxy) 4h Spiro(naphthalene 1,2' Oxirane) 4 One 2 (phenylamino) 4h Spiro(naphthalene 1,2' Oxirane) 4 One 2 Amino 4h Spiro(naphthalene 1,2' Oxirane) 4 One 2,2 Dimethyl 2,3 Dihydro 4h Spiro[naphtho[2,3 B]furan 9,2' Oxiran] 4 One 2,3 Dichloro 4h Spiro(naphthalene 1,2' Oxirane) 4 One 4,5 Dichloro 3,6 Dimethoxyphthalonitrile 4,5,7,8 Tetrachloro 1 Oxaspiro[2.5]octa 4,7 Dien 6 One Antimalarial Agent Chloroquine Ethylene Oxide Ethylene Oxide Derivative Methyl 9 Phenanthryl Ether Naphthoquinone Quinone Derivative Unclassified Drug Antimalarial Agent Ethylene Oxide Quinone Derivative Antimalarial Activity Controlled Study Drug Screening Drug Structure Drug Synthesis Ic 50 In Vitro Study Inhibitory Concentration Nonhuman Plasmodium Plasmodium Falciparum X-ray Diffraction Cell Line Cell Survival Chemical Structure Chemistry Dose Response Drug Effects Drug Sensitivity Fibroblast Human Structure Activity Relation Synthesis Antimalarials Cell Line Cell Survival Dose-response Relationship, Drug Ethylene Oxide Fibroblasts Humans Molecular Structure Parasitic Sensitivity Tests Plasmodium Falciparum Quinones Structure-activity Relationship
Data do documento:	2016
Revista:	European Journal of Medicinal Chemistry
É parte de:	Volume 108, Pags. 134-140
Abstract:	A series of eighteen quinones and structurally-related oxiranes were synthesized and evaluated for in vitro inhibitory activity against the chloroquine-sensitive 3D7 clone of the human malaria parasite Plasmodium falciparum. 2-amino and 2-allyloxynaphthoquinones exhibited important antiplasmodial activity (median inhibitory concentrations (IC50) < 10 μM). Oxiranes 6 and 25, prepared respectively by reaction of α-lapachone and tetrachloro-p-quinone with diazomethane in a mixture of ether and ethanol, exhibited the highest antiplasmodial activity and low cytotoxicity against human fibroblasts (MCR-5 cell line). The active compounds could represent a good prototype for an antimalarial lead molecule. © 2015 Published by Elsevier Masson SAS.
DOI:	10.1016/j.ejmech.2015.11.020
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