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( 1 H NMR), mass spectrometry(MS), infrared spectrometry(IR) and X-ray diffraction. The compound was crystallized in the orthorhombic system, space group P 2 1 2 1 2 1 with unit cell dimensions a= 0.60563(12) nm, b =1.0234(2) nm, c =3.2654(7) nm, α =90°, β =90°, γ =90°, 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 prodrug can significantly decrease the irritation after oral administration.