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Title: Amide-controlled, one-pot synthesis of tri-substituted purines generates structural diversity and analogues with trypanocidal activity.
Authors: Pineda de las Infantas y Villatoro, Maria J
Unciti-Broceta, Juan D
Contreras-Montoya, Rafael
Garcia-Salcedo, Jose A
Gallo Mezo, Miguel A
Unciti-Broceta, Asier
Diaz-Mochon, Juan J
metadata.dc.contributor.authoraffiliation: [Pineda de las Infantas y Villatoro,MJ; Gallo Mezo,MA; Diaz-Mochon,JJ] Departamento de Química Farmacéutica y Orgánica. University of Granada, Granada, Spain. [Unciti-Broceta,JD; Contreras-Montoya,R; Garcia-Salcedo,JA; Diaz-Mochon,JJ] Pfizer - Universidad de Granada - Junta de Andalucía Centre for Genomics and Oncological Research (GENYO),Granada, Spain. [Garcia-Salcedo,JA] Unidad de Enfermedades Infecciosas y Microbiología, Complejo Hospitalario de Granada. Instituto de Investigación Biosanitaria de Granada, Granada, Spain. [ Unciti-Broceta,A] Edinburgh Cancer Research UK Centre, MRC Institute of Genetics and Molecular Medicine, University of Edinburgh, Edinburgh, UK.
Keywords: Técnicas de químicas sintética;Purinas;Tripanocidas;Trypanosoma brucei brucei;Amidas
metadata.dc.subject.mesh: Medical Subject Headings::Chemicals and Drugs::Chemical Actions and Uses::Pharmacologic Actions::Therapeutic Uses::Anti-Infective Agents::Antiparasitic Agents::Antiprotozoal Agents::Trypanocidal Agents
Medical Subject Headings::Organisms::Eukaryota::Euglenozoa::Kinetoplastida::Trypanosomatina::Trypanosoma::Trypanosoma brucei brucei
Medical Subject Headings::Chemicals and Drugs::Heterocyclic Compounds::Heterocyclic Compounds, 2-Ring::Purines
Medical Subject Headings::Chemicals and Drugs::Organic Chemicals::Amides
Medical Subject Headings::Phenomena and Processes::Chemical Phenomena::Organic Chemistry Phenomena::Organic Chemistry Processes::Chemistry Techniques, Synthetic
Issue Date: 16-Mar-2015
Publisher: Nature Publishing Group
Citation: Pineda de las Infantas y Villatoro MJ, Unciti-Broceta JD, Contreras-Montoya R, Garcia-Salcedo JA, Gallo Mezo MA, Unciti-Broceta A, et al. Amide-controlled, one-pot synthesis of tri-substituted purines generates structural diversity and analogues with trypanocidal activity. Sci Rep. 2015; 5:9139
Abstract: A novel one-pot synthesis of tri-substituted purines and the discovery of purine analogues with trypanocidal activity are reported. The reaction is initiated by a metal-free oxidative coupling of primary alkoxides and diaminopyrimidines with Schiff base formation and subsequent annulation in the presence of large N,N-dimethylamides (e.g. N,N-dimethylpropanamide or larger). This synthetic route is in competition with a reaction previously-reported by our group, allowing the generation of a combinatorial library of tri-substituted purines by the simple modification of the amide and the alkoxide employed. Among the variety of structures generated, two purine analogues displayed trypanocidal activity against the protozoan parasite Trypanosoma brucei with IC50 < 5 μM, being each of those compounds obtained through each of the synthetic pathways.
Description: Journal Article; Research Support, Non-U.S. Gov't;
metadata.dc.identifier.doi: 10.1038/srep09139
ISSN: 2045-2322 (Online)
Appears in Collections:01- Artículos - Complejo Hospitalario Universitario de Granada
01- Artículos - GENYO. Centro Pfizer-Andalucía de Genómica e Investigación Oncológica
01- Artículos - ibsGRANADA. Instituto de Investigación Biosanitaria de Granada

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