1. Domino Synthesis of Embelin Derivatives with Antibacterial Activity
- Author
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Pedro Angel Martín Martín, Ana Estévez-Braun, Félix Machín, Gabriela Egly Feresin, Alejandro Tapia, and Rosalyn Peña
- Subjects
Staphylococcus aureus ,Proline ,Dihydropyran ,ANTIBACTERIAL ACTIVITY ,Pharmaceutical Science ,Stereoisomerism ,010402 general chemistry ,Gram-Positive Bacteria ,01 natural sciences ,Catalysis ,Analytical Chemistry ,Adduct ,chemistry.chemical_compound ,Drug Discovery ,Benzoquinones ,Organic chemistry ,Pharmacology ,Aldehydes ,Molecular Structure ,010405 organic chemistry ,Chemistry ,Otras Ciencias Químicas ,Organic Chemistry ,Anti-Inflammatory Agents, Non-Steroidal ,Ciencias Químicas ,0104 chemical sciences ,Anti-Bacterial Agents ,Complementary and alternative medicine ,Intramolecular force ,Molecular Medicine ,Knoevenagel condensation ,EMBELIN DERIVATES ,Antibacterial activity ,Cis–trans isomerism ,CIENCIAS NATURALES Y EXACTAS - Abstract
A series of dihydropyran embelin derivatives was synthesized through a direct and highly efficient approach based on a domino Knoevenagel intramolecular hetero-Diels–Alder reaction from natural embelin (1), using unsaturated aldehydes in the presence of organocatalysts such as ethylendiamine diacetate or l-proline. The aliphatic aldehydes yielded exclusively trans adducts, while mixtures of trans and cis isomers were found in reactions with aromatic aldehydes, with the cis form always predominating. Some of the compounds obtained were active and selective against Gram-positive bacteria, including multiresistant Staphylococcus aureus clinical isolates. Fil: Peña, Rosalyn. Universidad de la Laguna. Departamento de Química Orgánica. Instituto Universitario de Bio-Orgánica ; España Fil: Martín, Pedro. Universidad de la Laguna. Departamento de Química Orgánica. Instituto Universitario de Bio-Orgánica ; España Fil: Feresin, Gabriela Egly. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; Argentina. Universidad Nacional de San Juan. Facultad de Filosofía, Humanidades y Artes. Instituto de Ciencias Básicas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina Fil: Tapia, Aníbal Alejandro. Universidad Nacional de San Juan. Facultad de Ingeniería. Instituto de Biotecnología; Argentina. Universidad Nacional de San Juan. Facultad de Filosofía, Humanidades y Artes. Instituto de Ciencias Básicas; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina Fil: Machín, Félix. Hospital Universitario Nuestra Señora de Candelaria; España Fil: Estevez Braun, Ana. Universidad de la Laguna. Departamento de Química Orgánica. Instituto Universitario de Bio-Orgánica ; España
- Published
- 2016
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