Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (7): 1391-1398.DOI: 10.6023/cjoc201401047 Previous Articles     Next Articles



徐之涵, 潘燊, 黄焰根   

  1. 东华大学化学化工与生物工程学院 国家染整工程技术研究中心 上海 201620
  • 收稿日期:2014-02-11 修回日期:2014-03-31 发布日期:2014-04-01
  • 通讯作者: 黄焰根
  • 基金资助:


Synthesis and Biological Evaluation of New Retinoid Derivatives

Xu Zhihan, Pan Shen, Huang Yangen   

  1. College of Chemistry Chemical Engineering and Biotechnology, National Engineering Research Center for Dyeing and Finishing of Textiles, Donghua University, Shanghai 201620
  • Received:2014-02-11 Revised:2014-03-31 Published:2014-04-01
  • Supported by:

    Project supported by the Innovation Program of Shanghai Municipal Education Commission (No. 13ZZ047), the Scientific Research Foundation for the Returned Overseas Chinese Scholars (No. 2011-1139) and the State Education Ministry and the Fundamental Research Funds for the Central Universities.

The key intermediate boronic acid 2 was synthesized via sequential reactions of Friedel-Crafts alkylation, bromination and nucleophilic reaction by using anisole as starting material. Hydroxyacetone was converted to bromide compound 3 by the Wittig reaction, bromination, Arbuzov reaction and Horner-Wadsworth-Emmons (HWE) reaction. Three novel retinoid derivatives 1a1c can be obtained via the Suzuki coupling reaction of the boronic acid 2 with bromide compound 3, methyl 4-bromo-2-fluorobenzoate (4) or methyl 6-bromonicotinate (5) and followed by hydrolysis of the corresponding esters. In addition, trifluoromethyl substituted retinoid derivative 1d was synthesized via sequential reactions of Friedel-Crafts alkylation, nitration, trifluoromethylation, reduction and nucleophilic reaction with bromobenzene as strarting material. The structures of four new retinoid derivatives 1a1d were confirmed by 1H NMR, 13C NMR, IR and HRMS analyses. Furthermore, the inducing differentiation abilities of molecules 1a1d for HL-60 cells were tested, and the results revealed that these four retinoid derivatives are biological active. The IC50 values of fluorinated derivatives 1b and 1d are lower than that of commercial medicine all trans retinoid acid (ATRA).

Key words: retinoid derivative, synthesis, organofluorine compounds, antineoplastic