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