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-Vázquez
  • Héctor Torres-Gómez
  • Jorge Guerrero-Álvarez
  • Hugo Tlahuext
Original Paper

Abstract

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, R1 = 0.0465, and wR2 = 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.

Keywords

Fibrates Antidislypidemic activity Crystal structure Hydrogen bonds 

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Copyright information

© Springer Science+Business Media, LLC 2011

Authors and Affiliations

  • Gabriel Navarrete-Vázquez
    • 1
  • 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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