Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (4): 809-816.DOI: 10.6023/cjoc201309030 Previous Articles     Next Articles

Articles

新型咔唑类衍生物的合成、光谱性质及其与Ct-DNA作用的研究

简勇, 李刚, 杨鹏, 邓拓, 周雪, 徐海燕   

  1. 基于靶点的药物设计与研究教育部重点实验室 沈阳药科大学 沈阳 110016
  • 收稿日期:2013-09-23 修回日期:2013-11-18 出版日期:2014-04-25 发布日期:2013-12-06
  • 通讯作者: 杨鹏 E-mail:pengyangcn05@hotmail.com
  • 基金资助:

    国家自然科学基金(No. 21102095)、辽宁省自然科学基金(No. 201102209)、辽宁省高校杰出青年学者成长计划(No. LJQ2012090)、辽宁省首批“博士后集聚工程”(No. 2011921013)和辽宁省“大学生创新创业训练计划” (No. 201210163012)资助项目

Syntheses, Spectral Properties of Novel Carbazole Derivatives and Evaluations of Its Ct-DNA Interaction

Jian Yong, Li Gang, Yang Peng, Deng Tuo, Zhou Xue, Xu Haiyan   

  1. Key Laboratory of Structure-Based Drug Design and Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016
  • Received:2013-09-23 Revised:2013-11-18 Online:2014-04-25 Published:2013-12-06
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21102095), the Liaoning Provincial Natural Science Foundation (No. 201102209), the Program of Liaoning Excellent Talents in University (No. LJQ2012090), the Liaoning Provincial Postdoctoral Converging Project (No. 2011921013), and the Undergraduates Innovative Entrepreneurship Training Project of Liaoning Province (No. 201210163012).

A series of carbazole derivatives were synthesized via reactions of C—N bond formation catalyzed by CuBr·SMe2, nitration, reduction as well as Pd-catalyzed C—N crossing coupling, respectively. Their UV-Vis and fluorescence spectra in different solvents were investigated, as well as the evaluation of the interaction between compound 2 hydrochloride and Ct-DNA. The results showed that all compounds exhibited distinct solvatochromism effects and among them, compound 4 was the most obvious one. Upon binding with DNA, the fluorescence of compound 2 hydrochloride turned on, instead of quenching, and the minor groove of DNA is the most possible position for the molecule to bind with. The calculated binding constant is around 104 L·mol-1, showing a moderate binding affinity.

Key words: carbazole, C—N cross coupling, solvatochromism, spectral properties, Ct-DNA