Journal of Chemical Crystallography

, Volume 41, Issue 5, pp 732–736 | Cite as

Synthesis and Crystal Structure of Ethyl 2-[4-(acetylamino)phenoxy]-2-methylpropanoate, A Potential Anti-inflammatory and Antidyslipidemic Hybrid

  • Gabriel Navarrete-VázquezEmail author
  • Héctor Torres-Gómez
  • Jorge Guerrero-Álvarez
  • Hugo Tlahuext
Original Paper


The compound ethyl 2-[4-(acetylamino)phenoxy]-2-methylpropanoate (acetamidofibrate) was prepared by reaction of paracetamol with ethyl 2-bromo-2-methylpropionate. It was characterized by elemental analysis, NMR (1H, 13C) spectroscopy, and single-crystal X-ray diffraction. This compound is of interest with respect to its potential bioactivity as analgesic and antidyslipidemic agent. The compound crystallizes in the monoclinic space group P2(1)/c with unit cell dimensions a = 8.2435(8), b = 9.3390(9), c = 18.2823(18) Å, β = 91.123(2)°, V = 1407.2(2) Å3, Z = 4, R 1 = 0.0465, and wR 2 = 0.1055. The crystal structure is stabilized by N–H···O = C and C–H···O hydrogen-bonding interactions that interconnect molecules into chains running along b axis. The preliminary in silico screening shown that title compound could posse’s antidiabetic, anti-inflammatory, hypolipemiant and anti-atherosclerosis effects.

Graphical Abstract

The title compound was synthesized and characterized by elemental analysis, 1H and 13C NMR and single-crystal X-ray diffraction. This compound is of interest with respect to its potential bioactivity as analgesic and antidyslipidemic agent.


Fibrates Antidislypidemic activity Crystal structure Hydrogen bonds 



This work was supported by the Consejo Nacional de Ciencia y Tecnología (CONACyT) under grant No. 100608, Facultad de Farmacia internal grant, and Fondo de Consolidación PROMEP-UAEM/09/349. HTG is grateful to CONACyT for the scholarship grant 228019 to carry out Master degree studies.


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Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • Gabriel Navarrete-Vázquez
    • 1
    Email author
  • Héctor Torres-Gómez
    • 1
  • Jorge Guerrero-Álvarez
    • 2
  • Hugo Tlahuext
    • 2
  1. 1.Facultad de FarmaciaUniversidad Autónoma del Estado de MorelosCuernavacaMexico
  2. 2.Centro de Investigaciones QuímicasUniversidad Autónoma del Estado de MorelosCuernavacaMexico

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