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Chinese Journal of Organic Chemistry ›› 2004, Vol. 24 ›› Issue (2): 210-215. Previous Articles     Next Articles

S-烃基-1-烃基-3-[4-(5-取代苯并咪唑-2-巯基)苯基]异硫脲的合成及生物活性

徐云根, 罗穗†, 华维一*, 朱东亚   

  1. 中国药科大学新药研究中心 南京 210009
  • 收稿日期:2003-05-06 修回日期:2003-08-04 接受日期:2003-09-01 发布日期:2022-09-20
  • 作者简介:†现在广东省药品监督管理局工作.
  • 基金资助:
    国家自然科学基金(No. 39670856)资助项目.†现在广东省药品监督管理局工作

Synthesis and Biological Activity of S-Alkyl (or Aralkyl)-1-alkyl (or aryl)-3- [4-(5-methoxy (or chloro)benzimidazole-2-mercapto)phenyl]isothioureas

XU, Yun-Gen, LUO, Sui†, HUA, Wei-Yi*, ZHU, Dong-Ya   

  1. Center of Drug Discovery, China Pharmaceutical University, Nanjing 210009
  • Received:2003-05-06 Revised:2003-08-04 Accepted:2003-09-01 Published:2022-09-20
  • Contact: * E-mail: huawy36@yahoo.com.cn

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In order to get some novel compoundswith potent iNOS inhibitory activity for the treatment of septic shock and inflammation, 12 target compounds of S-alkyl (or aralkyl)-1-alkyl (or aryl)-3-[4-(5-methoxy (or chloro)-benzimidazole-2-mercapto)phenyl]isothioureas(5a～5l) were synthesized. Firstly, 2-mercapto-5-methoxy (or chloro)benzimidazole (1) were converted into 5-methoxy (or chloro)-2-(4-nitrophenylmercapto)benzimidazole (2) by condensation with 1-chloro-4-nitrobenzene. Secondly, reductionof 2 afforded 5-methoxy (or chloro)-2-(4-aminophenylmercapto)benzimidazole (3). Then 3 were converted into corresponding 1,3-disubstituted thioureas 4 by reaction with alkyl (or aryl) isothiocyanate. Finally, the S-alkylation of 4 with alkyl iodide or (substituted)benzyl halogen was carried out to obtain the targetcompounds 5a～5l. The structures of the compounds were confirmed by IR, MS, 1H NMR spectra and elemental analysis. Theresults of preliminary pharmacological test showed that all of compounds possess higher iNOS inhibitory activity than the control aminoguanidine.

Key words: iNOS inhibitor, isothiourea, inflammation, septic shock