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高等学校化学研究 ›› 2013, Vol. 29 ›› Issue (2): 245-248.doi: 10.1007/s40242-013-2266-9

• Articles • 上一篇    下一篇

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

LIANG Di1,2, YANG Xiao-hong1, SUN Wei1, WANG Wen-na1, YANG Jin-zhu1, LIU Yin-yan1, WANG Guang-shu1   

  1. 1. School of Pharmaceutical Sciences, Jilin University, Changchun 130021, P. R. China;
    2. The Second Hospital, Jilin University, Changchun 130041, P. R. China
  • 收稿日期:2012-07-10 修回日期:2012-08-09 出版日期:2013-04-01 发布日期:2013-03-20
  • 通讯作者: WANG Guang-shu E-mail:wgs@jlu.edu.cn

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

LIANG Di1,2, YANG Xiao-hong1, SUN Wei1, WANG Wen-na1, YANG Jin-zhu1, LIU Yin-yan1, WANG Guang-shu1   

  1. 1. School of Pharmaceutical Sciences, Jilin University, Changchun 130021, P. R. China;
    2. The Second Hospital, Jilin University, Changchun 130041, P. R. China
  • Received:2012-07-10 Revised:2012-08-09 Online:2013-04-01 Published:2013-03-20

摘要：

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.

关键词: Naproxen-eugenol ester, Crystal structure, Biological activity

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