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Acta Chimica Sinica ›› 2006, Vol. 64 ›› Issue (11): 1151-1156. Previous Articles     Next Articles

Original Articles

3-芳氧基-1-丙胺类HIV-1 Tat/PCAF BRD抑制剂的合成及生物活性

李家明1，汪志勇*,1，ZENG, Lei2，ZHOU, Ming-Ming*,2   

  1. (1中国科学技术大学化学系 合肥 230026)
    (2 Structural Biology Program, Department of Physiology and Biophysics, Mount Sinai School of Medicine, New York
    University, New York 10029-6574, U. S. A.)
  • 投稿日期:2005-08-26 修回日期:2006-02-14 发布日期:2006-06-15
  • 通讯作者: 汪志勇

Synthesis and Biological Acitivity of 3-Aryloxy-1-propylamineDerivatives as HIV-1 Tat/PCAF BRD Inhibitor

LI Jia-Ming1, WANG Zhi-Yong*,1, ZENG Lei2, ZHOU Ming-Ming*,2   

  1. (1 Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, China)
    (2 Structural Biology Program, Department of Physiology and Biophysics, Mount Sinai School of Medicine, New York University, New York 10029-6574, U. S. A.)
  • Received:2005-08-26 Revised:2006-02-14 Published:2006-06-15
  • Contact: WANG Zhi-Yong

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Six 3-aryloxy-1-propylamines were synthesized for studying the SAR of HIV-1 Tat/PCAF BRD inhibitors. Substituted 2-nitrophenol reacted with 1,3-dibromopropane to give 3-(2-nitroaryloxy)-1-propylbromides (3) under common heating and microwave irradiation, the reaction rate was accelerated remarkably and the yields were increased under microwave irradiation in comparision with that under common heating. Compound 3 were treated with potassium phthalimide to produce 2-[3-(aryloxy)-propyl]isoindoline-1, 3-dione (4). Hydrazinolysis of compound 4 yielded target molecules. The structures of all compounds were characterized by FTIR, 1H NMR, 13C NMR and HRMS spectra. The inhibition of HIV-1 Tat/PCAF BRD interaction in vitro was determined by ELISA assay, and some influential factors of biological activity were discussed.

Key words: 3-aryloxy-1-propylamine hydrochloride, microwave irradiation, hydrazinolysis, Gabriel reaction, anti-HIV-1