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A simple method for the synthesis of 1,3-diaminopropan-2-ols derivatives and their ex vivo relaxant activity on isolated rat tracheal rings

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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.

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Acknowledgements

M.A.V. acknowledges CONACYT (Grant 168474) and DAIP-UGto (Grant 811/16) for financial support. F.I.L, F. N. de la C. and J.L. thanks CONACYT for graduate scholarships (No. 481806, 366790, 329994 respectively). We thank Guanajuato National Laboratory (CONACyT 260373) for generous allocation of analytical resources.

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Authors and Affiliations

  1. Departamento de Química, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Noria Alta S/N, Guanajuato, 36050, Gto., Mexico

    Fabiola I. López, Fabiola N. de la Cruz, Julio López, J. Merced Martínez & Miguel A. Vázquez

  2. Departamento de Farmacia, División de Ciencias Naturales y Exactas, Universidad de Guanajuato, Noria Alta S/N, Guanajuato, 36050, Gto., Mexico

    Yolanda Alcaraz

  3. Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas-IPN, Prol. Carpio y Plan de Ayala S/N, Ciudad de, 11340, DF, Mexico

    Francisco Delgado

  4. Facultad de Farmacia, Universidad Autónoma del Estado de Morelos, Cuernavaca, 62209, Mor., Mexico

    Amanda Sánchez-Recillas & Samuel Estrada-Soto

Authors
  1. Fabiola I. López
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  2. Fabiola N. de la Cruz
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  3. Julio López
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  4. J. Merced Martínez
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  5. Yolanda Alcaraz
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  6. Francisco Delgado
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  7. Amanda Sánchez-Recillas
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  8. Samuel Estrada-Soto
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  9. Miguel A. Vázquez
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Correspondence to Samuel Estrada-Soto or Miguel A. Vázquez.

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López, F.I., de la Cruz, F.N., López, J. et al. A simple method for the synthesis of 1,3-diaminopropan-2-ols derivatives and their ex vivo relaxant activity on isolated rat tracheal rings. Med Chem Res 26, 1325–1335 (2017). https://doi.org/10.1007/s00044-017-1853-6

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  • DOI: https://doi.org/10.1007/s00044-017-1853-6

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