Synthesis, Crystal Structure and Biological Activities of Naproxen-eugenol Ester Prodrug

doi:10.1007/s40242-013-2266-9

Abstract

Abstract:

The prodrug, naproxen-eugenol ester, was synthesized by acyl chloride method with naproxen and eugenol as the raw materials. The structure was identified by proton nuclear magnetic resonance(¹H NMR), mass spectrometry(MS), infrared spectrometry(IR) and X-ray diffraction. The compound was crystallized in the orthorhombic system, space group P2₁2₁2₁ with unit cell dimensions a=0.60563(12) nm,b=1.0234(2) nm, c=3.2654(7) nm, a=90°, b=90°, g=90°, V=2.0240(7) nm³, Z=4. Calculated density 1.235 Mg/m³; absorption coefficient: 0.083 mm^-1; F(000)=800; final R₁=0.0564. The analgesic activity and anti-inflammatory were similar to those of naproxen, and the results of ulcerogenic activity indicate that the prodrug can significantly decrease the irritation after oral administration.

Key words: Naproxen-eugenol ester, Crystal structure, Biological activity

LIANG Di, YANG Xiao-hong, SUN Wei, WANG Wen-na, YANG Jin-zhu, LIU Yin-yan, WANG Guang-shu. Synthesis, Crystal Structure and Biological Activities of Naproxen-eugenol Ester Prodrug[J]. Chemical Research in Chinese Universities, 2013, 29(2): 245-248.

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Synthesis, Crystal Structure and Biological Activities of Naproxen-eugenol Ester Prodrug

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