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

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(H-1 NMR), mass spectrometry(MS), infrared spectrometry(IR) and X-ray diffraction. The compound was crystallized in the orthorhombic system, space group P2(1)2(1)2(1) with unit cell dimensions alpha=0.60563(12) nm, b=1.0234(2) nm, c=3.2654(7) nm, alpha=90 degrees, beta=90 degrees, gamma=90 degrees, V=2.0240(7) nm(3), Z=4. Calculated density 1.235 Mg/m(3); absorption coefficient: 0.083 mm(-1); F(000)=800; final R-1=0.0564. The analgesic activity and anti-inflammatory were similar to those of naproxen, and the results of ulcerogenic activity indicate that the pro drug can significantly decrease the irritation after oral administration.