研究简报

含苯并咪唑环二酰肼衍生物的合成与结构表征

  • 李英俊 ,
  • 于洋 ,
  • 许永廷 ,
  • 靳焜 ,
  • 罗潼川 ,
  • 邵昕 ,
  • 史相玲 ,
  • 吴疆红
展开
  • a 辽宁师范大学化学化工学院 大连116029;
    b 辽宁师范大学分析测试中心 大连116029;
    c 大连理工大学精细化工国家重点实验室 大连116012

网络出版日期: 2013-03-07

Synthesis and Characterization of Dihydrazide Derivatives Containing Benzimidazole Ring

  • Li Yingjun ,
  • Yu Yang ,
  • Xu Yongting ,
  • Jin Kun ,
  • Luo Tongchuan ,
  • Shao Xin ,
  • Shi Xiangling ,
  • Wu Jianghong
Expand
  • a College of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029;
    b Analysis and Inspection Center, Liaoning Normal University, Dalian 116029;
    c State Key Laboratory of Fine Chemicals, Dalian University of Technology, Dalian 116012

Online published: 2013-03-07

Supported by

Project supported by the Natural Science Foundation of Liaoning Province (No. 20102126).

摘要

以酚和氯乙酸为初始原料, 经一系列反应, 合成出了10 个新型的含苯并咪唑环二酰肼衍生物(7a~7j。利用1H NMR、13C NMR、2D NMR(包括HMBC、HSQC、1H-1H COSY和NOESY)和变温1H NMR技术对代表化合物 7c进行了1H 和13C NMR谱归属并确定了其空间结构, 证明了其在室温及DMSO中存在着A和B两种互变异构体, 并且A异构体占优势(87.65%)。据此, 对其它目标化合物的1H NMR也进行了归属, A异构体含量为80.55%~89.90%。

关键词: 二酰肼; 合成; 表征

本文引用格式

李英俊 , 于洋 , 许永廷 , 靳焜 , 罗潼川 , 邵昕 , 史相玲 , 吴疆红 . 含苯并咪唑环二酰肼衍生物的合成与结构表征[J]. 有机化学, 0 , (0) : 0 -0 . DOI: 10.6023/cjoc201301009

Abstract

Ten novel dihydrazide derivatives containing benzimidazole ring (7a7j) were synthesized by (un)substituted phenol and chloroacetic acid as starting materials via a series of reactions. The structure of representative compound 7c was confirmed by its 1H NMR, 13C NMR, 2D NMR (1H-1H COSY, HSQC, HMBC and NOESY) and variable-temperature 1H NMR spectra. The experimental results indicate that compound 7c in DMSO at room temperature exists in the tautomeric A and B isomers, and A isomer is dominant (87.65%). On the basis of the analytic results of compound 7c, 1H NMR spectra of other target compounds were also assigned and the content of dominant A isomer is in the range of 80.55%~89.90%.

参考文献

[1] Demirayak, S.; Kayagil, I.; Yurttas, L. Eur. J. Med. Chem. 2011, 46, 411.

[2] Woo, H. B.; Eom, Y. W.; Park, Kyu-Sang; Ham, J.; Ahn, C. M.; Lee, S. Bioorg. Med. Chem. Lett. 2012, 22, 933.

[3] Li, Y.-J.; Liu, L.-J.; Jin, K.; Sun, S.-Q.; Xu, Y.-T. Acta Chim. Sinica 2010, 68(16), 1577 (in Chinese). (李英俊, 刘丽军, 靳焜, 孙淑琴, 许永廷, 化学学报, 2010, 68(16), 1577.)

[4] Kaushik, D.; Khan, S. A.; Chawla G. Med. Chem. Res. 2012, 21, 459.

[5] Soni, L. K.; Narsinghani, T.; Sethi, A. Med Chem Res. 2012, 21, 4330.

[6] Hernández-Luis, F.; Hernández-Campos, A.; Castillo, R.; Navarrete-Vázquez, G.; Soria-Arteche, O.; Hernández-Hernández, M.; Yépez-Muli, L. Eur. J. Med. Chem. 2010, 45, 3135.

[7] Schmidt, S.; Preu, L.; Lemcke, T.; Totzke, F.; Sch?chtele, C.; Kubbutat, M. H. G.; Kunick, C. Eur. J. Med. Chem. 2011, 46, 2759.

[8] Hearn, M. J.; Cynamon, M. H. Drug Design and Discovery 2003, 18, 103.

[9] Thomas, K. D.; Adhikari, A. V.; Telkar, S.; Telkar, S.; Chowdhury, I. H.; Mahmood, R.; Pal, N. K.; Row, G.; Sumesh, E. Eur. J. Med. Chem. 2011, 46, 5283.

[10] Kovganko, N. V.; Ananich, S. K. Russ. J. Bioorg. Chem. 2004, 30, 505.

[11] Parra, M.; Hidalgo, P.; Barberá, J.; Carrasco, E.; Saavedra, C. Liq. Cryst. 2006, 33, 391.

[12] Li, Y.-J.; Liu, L,-J.; Jin, K.; Wang, W.; Zhao, N.; Li, L.-N.; Li, C.-Y. Chin. J. Org. Chem. 2009, 29(11), 1825 (in Chinese). (李英俊, 刘丽军, 靳焜, 王巍, 赵楠, 李丽娜, 李春燕, 有机化学, 2009, 29(11), 1825.)

[13] Li, L.-N. M.S. Thesis, Liaoning Normal University, Dalian, 2011 (in Chinese). (李丽娜, 硕士论文, 辽宁师范大学, 大连, 2011.)

[14] Cativiela, C.; Serrano, J. L.; Zurbano, M. M. J. Org. Chem. 1995, 60, 3074.

[15] Li, Y.-J.; Ding, W.-G.; Jin, K.; Sun, S.-Q.; Liu, J.; Liu, L,-J.; Wang, J.-K. Chin. J. Org. Chem. 2009, 29(1), 82 (in Chinese). (李英俊, 丁万刚, 靳焜, 孙淑琴, 刘军, 刘丽军, 王金奎, 有机化学, 2009, 29(1), 82.)

Options
文章导航

/