Medicinal Chemistry Research

, Volume 26, Issue 6, pp 1325–1335 | Cite as

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

  • Fabiola I. López
  • Fabiola N. de la Cruz
  • Julio López
  • J. Merced Martínez
  • Yolanda Alcaraz
  • Francisco Delgado
  • Amanda Sánchez-Recillas
  • Samuel Estrada-Soto
  • Miguel A. Vázquez
Original Research
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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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Keywords

1,3-Diaminopropan-2-ols Mixed metal oxides Rat tracheal relaxation Anti-asthmatic effect 
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Notes

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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Conflict of interest

The authors declare that they have no conflicts of interest.

Supplementary material

44_2017_1853_MOESM1_ESM.docx (5.2 mb)
Supplementary Information

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Copyright information

© Springer Science+Business Media New York 2017

Authors and Affiliations

  • Fabiola I. López
    • 1
  • Fabiola N. de la Cruz
    • 1
  • Julio López
    • 1
  • J. Merced Martínez
    • 1
  • Yolanda Alcaraz
    • 2
  • Francisco Delgado
    • 3
  • Amanda Sánchez-Recillas
    • 4
  • Samuel Estrada-Soto
    • 4
  • Miguel A. Vázquez
    • 1
  1. 1.Departamento de Química, División de Ciencias Naturales y ExactasUniversidad de GuanajuatoGuanajuatoMexico
  2. 2.Departamento de Farmacia, División de Ciencias Naturales y ExactasUniversidad de GuanajuatoGuanajuatoMexico
  3. 3.Departamento de Química OrgánicaEscuela Nacional de Ciencias Biológicas-IPNCiudad deMexico
  4. 4.Facultad de FarmaciaUniversidad Autónoma del Estado de MorelosCuernavacaMexico

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