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Semisynthesis, ex vivo evaluation, and SAR studies of coumarin derivatives as potential antiasthmatic drugs.
Sánchez-Recillas, Amanda; Navarrete-Vázquez, Gabriel; Hidalgo-Figueroa, Sergio; Rios, María Yolanda; Ibarra-Barajas, Maximiliano; Estrada-Soto, Samuel.
Afiliação
  • Sánchez-Recillas A; Laboratorio de Farmacognosia y Química de Productos Naturales, Facultad de Farmacia, Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Col. Chamilpa, 62209 Cuernavaca, Morelos, Mexico.
  • Navarrete-Vázquez G; Laboratorio de Química Farmacéutica, Facultad de Farmacia, Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Col. Chamilpa, 62209 Cuernavaca, Morelos, Mexico. Electronic address: gabriel_navarrete@uaem.mx.
  • Hidalgo-Figueroa S; Laboratorio de Química Farmacéutica, Facultad de Farmacia, Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Col. Chamilpa, 62209 Cuernavaca, Morelos, Mexico.
  • Rios MY; Centro de Investigaciones Químicas, Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Col. Chamilpa, 62209 Cuernavaca, Morelos, Mexico.
  • Ibarra-Barajas M; Unidad de Biomedicina, Facultad de Estudios Superiores Iztacala, Universidad Nacional Autónoma de México, 54090 Tlalnepantla, Estado de México, Mexico.
  • Estrada-Soto S; Laboratorio de Farmacognosia y Química de Productos Naturales, Facultad de Farmacia, Universidad Autónoma del Estado de Morelos, Avenida Universidad 1001, Col. Chamilpa, 62209 Cuernavaca, Morelos, Mexico. Electronic address: enoch@uaem.mx.
Eur J Med Chem ; 77: 400-8, 2014 Apr 22.
Article em En | MEDLINE | ID: mdl-24681028
Asthma is a chronic inflammatory disorder that causes contraction in the smooth muscle of the airway and blocking of airflow. Reversal the contractile process is a strategy for the search of new drugs that could be used for the treatment of asthma. This work reports the semisynthesis, ex vivo relaxing evaluation and SAR studies of a series of 18 coumarins. The results pointed that the ether derivatives 1-3, 7-9 and 13-15 showed the best activity (Emax = 100%), where compound 2 (42 µM) was the most potent, being 4-times more active than theophylline (positive control). The ether homologation (methyl, ethyl and propyl) in position 7 or positions 6 and 7 of coumarins lead to relaxing effect, meanwhile formation of esters generated less active compounds than ethers. The SAR analysis showed that it is necessary the presence of two small ether groups and the methyl group at position 4 (site 3) encourage biological activity through soft hydrophobic changes in the molecule, without drastically affecting the cLogP.
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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Traqueia / Antiasmáticos / Cumarínicos Limite: Animals Idioma: En Revista: Eur J Med Chem Ano de publicação: 2014 Tipo de documento: Article País de afiliação: México País de publicação: França
Texto completo
Adicionar na Minha BVS
Imprimir
XML
PubMed Links
Buscar no Google

Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Traqueia / Antiasmáticos / Cumarínicos Limite: Animals Idioma: En Revista: Eur J Med Chem Ano de publicação: 2014 Tipo de documento: Article País de afiliação: México País de publicação: França