TY - JOUR
T1 - A simple method for the synthesis of 1,3-diaminopropan-2-ols derivatives and their ex vivo relaxant activity on isolated rat tracheal rings
AU - López, Fabiola I.
AU - de la Cruz, Fabiola N.
AU - López, Julio
AU - Martínez, J. Merced
AU - Alcaraz, Yolanda
AU - Delgado, Francisco
AU - Sánchez-Recillas, Amanda
AU - Estrada-Soto, Samuel
AU - Vázquez, Miguel A.
N1 - Publisher Copyright:
© 2017, Springer Science+Business Media New York.
PY - 2017/6/1
Y1 - 2017/6/1
N2 - Abstract: A mild and eco-friendly method has been developed for the synthesis of a series of 1,3-diaminopropan-2-ols 8a–n. The epoxide of epichlorohydrin undergoes ring-opening with amines using MgSO4 or mixed metal oxides catalysts under mild and neutral conditions to afford the corresponding β-amino alcohols in excellent yields. Preliminary evaluation of relaxant activity of 8b–n was carried out on rat tracheal rings contracted by carbachol 1 μM. Most of the tested compounds exhibited significantly relaxant effects in a concentration-dependent manner. Compound 8n was found to be the most active, being twofolds more potent than theophylline (positive control). This compound has the potential for development as an anti-asthma drug. Graphical Abstract: [InlineMediaObject not available: see fulltext.].
AB - Abstract: A mild and eco-friendly method has been developed for the synthesis of a series of 1,3-diaminopropan-2-ols 8a–n. The epoxide of epichlorohydrin undergoes ring-opening with amines using MgSO4 or mixed metal oxides catalysts under mild and neutral conditions to afford the corresponding β-amino alcohols in excellent yields. Preliminary evaluation of relaxant activity of 8b–n was carried out on rat tracheal rings contracted by carbachol 1 μM. Most of the tested compounds exhibited significantly relaxant effects in a concentration-dependent manner. Compound 8n was found to be the most active, being twofolds more potent than theophylline (positive control). This compound has the potential for development as an anti-asthma drug. Graphical Abstract: [InlineMediaObject not available: see fulltext.].
KW - 1,3-Diaminopropan-2-ols
KW - Anti-asthmatic effect
KW - Mixed metal oxides
KW - Rat tracheal relaxation
UR - http://www.scopus.com/inward/record.url?scp=85015709728&partnerID=8YFLogxK
U2 - 10.1007/s00044-017-1853-6
DO - 10.1007/s00044-017-1853-6
M3 - Artículo
SN - 1054-2523
VL - 26
SP - 1325
EP - 1335
JO - Medicinal Chemistry Research
JF - Medicinal Chemistry Research
IS - 6
ER -