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2013 , Vol. 33 >Issue 9: 1945 - 1949

DOI: https://doi.org/10.6023/cjoc201304036

研究论文

噻唑啉-2-硫酮衍生物的合成与生物活性

  • 刘建超 ,
  • 梁英 ,
  • 贺红武
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  • a 华中师范大学化学学院 武汉 430079;
    b 湖北省农业科学院湖北省生物农药工程研究中心 武汉 430064

收稿日期: 2013-04-24

  修回日期: 2013-06-04

  网络出版日期: 2013-06-09

基金资助

国家重点基础研究发展规划(973计划, No. 2010CB126100);国家自然科学基金(Nos. 21172090, 31000867);教育部创新团队项目部分(No. IRT0953);国家科技支撑计划(No. 2011BAE06B04)资助项目

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Synthesis and Herbicidal Activity of Thiazolin-2-thione Derivatives

  • Liu Jianchao ,
  • Liang Ying ,
  • He Hongwu
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  • a College of Chemistry, Central China Normal University, Wuhan 430079;
    b Hubei Biopesticide Engineering Research Center, Hubei Academy of Agricultural Science, Wuhan 430064

Received date: 2013-04-24

  Revised date: 2013-06-04

  Online published: 2013-06-09

Supported by

Project supported by the National Program on Key Basic Research Project (973 Program, No. 2010CB126100), the National Natural Science Foundation of China (Nos. 21172090, 31000867), the Program for Changjiang Scholars and Innovative Research Team in University (No. IRT0953) and the Key Projects in the National Science & Technology Pillar Program (No. 2011BAE06B04)

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摘要

根据活性亚结构拼接原理, 将3-芳基-4-氨基-5-乙氧羰基(氰基)-3H-噻唑啉-2-硫酮与酰氯反应得到目标化合物3-芳基-4-取代苯氧乙酰氨基-5-乙氧羰基(氰基)-3H-噻唑啉-2-硫酮. 再以3-苯基-4-氨基-5-乙氧羰基-3H-噻唑啉-2-硫酮为合成原料, 经过Aza-Wittig反应得到目标化合物5-芳氧基-3,6-二芳基-2-硫代噻唑并[4,5-d]嘧啶-7-酮. 通过IR, 1H NMR, EI-MS, 元素分析等方法对所合成的化合物进行了结构表征. 代表化合物5-对氯苯氧基-3,6-二苯基-2-硫代- 2,3-二氢噻唑并[4,5-d]嘧啶-7(6H)-酮(C1)经单晶X衍射证实了结构. 除草活性测试结果表明: 部分噻唑啉-2-酮类衍生物对稗草和油菜都表现出了较好的抑制活性.

关键词： 噻唑啉-2-硫酮; 噻唑并[4,5-d]嘧啶; Aza-Wittig反应; 除草活性

本文引用格式

刘建超 , 梁英 , 贺红武 . 噻唑啉-2-硫酮衍生物的合成与生物活性[J]. 有机化学, 2013 , 33(9) : 1945 -1949 . DOI: 10.6023/cjoc201304036

Abstract

Ten 3-aryl-thiazolin-2-thione derivatives have been designed and synthesized by the reaction of 3-aryl-4-amino- 3H-thiazolin-2-thiones with phenoxyacetyl chloride and the aza-Wittig reactions of 3-aryl-4-amino-5-ethyloxyacyl- 3H-thiazolin-2-thione with phenols. The structures of target compounds have been confirmed by 1H NMR, EI-MS, IR spectroscopy and elemental analyses. The structure of 5-(4-Cl-phenoxy)-3,6-diphenyl-2-thioxo-2,3-dihydrothiazolo[4,5-d]- pyrimidin-7(6H)-one (C1) has been determined by single crystal X-ray diffraction. The results of preliminary bioassay indicated that some compounds possess good herbicidal activity against the roots of Rape and Barnyard grass.

Key words： thiazolin-2-thione; thiazolo[4,5-d]pyrimidine; aza-Wittig reaction; herbicidal activity

参考文献

[1] Nakatani, N.; Hasegawa, J.; Nakatsuji, H. J. Am. Chem. Soc. 2007, 129, 8756.
[2] Hofmann, B.; Barzen, S.; Rodl, C. B.; Kiehl, A.; Borig, J.; Zivkovic, A.; Stark, H.; Schneider, G.; Steinhilber, D. J. Med. Chem. 2011, 54, 1943.
[3] Jain, A. K.; Vaidya, A.; Ravichandran, V.; Kashaw, S. K. Bioorg. Med. Chem. 2012, 20, 3378.
[4] Takasu, K.; Pudhom, K.; Kaiser, M.; Brun, R.; Ihara, M. J. Med. Chem. 2006, 49, 4795.
[5] Wang, X.; Huang, G.; Quan, Z.; Lv, C.; Yang, W. Chin. J. Org. Chem. 2008, 28, 870 (in Chinese).
(王喜存, 黄国利, 权正军, 吕成伟, 杨文龙, 有机化学, 2008, 28, 870.)
[6] Sun, X.; Zhou, J.; Zhu, H. Chin. J. Org. Chem. 2011, 31, 242 (in Chinese).
(孙小军, 周建峰, 朱惠琴, 有机化学, 2011, 31, 242.)
[7] Bekhit, A. A.; Fahmy, H. T. Y.; Rostom, S. A. F.; Baraka, A. M. Eur. J. Med. Chem. 2003, 38, 27. [8] Brvar, M.; Perdih, A.; Hodnik, V.; Renko, M.; Anderluh, G.; Jerala, R.; Solmajer, T. Bioorg. Med. Chem. 2012, 20, 2572.
[9] Beck, J. P.; Curry, M. A.; Chorvat, R. J.; Fitzgerald, L. W.; Gilligan, P. J.; Zaczek, R.; Trainor, G. L. Bioorg. Med. Chem. Lett. 1999, 9, 1185.
[10] Luthra, P. M.; Mishra, C. B.; Jha, P. K.; Barodia, S. K. Bioorg. Med. Chem. Lett. 2010, 20, 1214.
[11] Li, Y.; Li, C.; Jin, K.; Sun, S.; Zhou, X. Acta Chim. Sin. 2012, 70, 151 (in Chinese).
(李英俊, 李春燕, 靳焜, 孙淑琴, 周晓霞, 化学学报, 2012, 70, 151.)
[12] Liang, Y.; Fan, S.; Mo, W. Y.; He, H. W. J. Fluorine Chem. 2007, 128, 879.
[13] Liang, Y.; He, H. W. Chin. J. Org. Chem. 2009, 29, 924 (in Chinese).
(梁英, 贺红武, 有机化学, 2009, 29, 924.)
[14] Chen, T.; Shen, P.; Li, Y. J.; He, H. W. J. Fluorine Chem. 2006, 127, 291.
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