Synthesis and Bioactivity of N-(5 -Bromo-4 -substituted pyrimidin-2 -yl)phenyl Sulfonylurea

Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (04): 564-568. Previous Articles Next Articles

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N-(5 -溴-4 -取代嘧啶-2 -基)苯磺酰脲化合物的合成和生物活性

班树荣*^{,1，牛聪伟²，陈文彬²，李青山¹，席真*^,2}

(¹山西医科大学药学院太原 030001)
(²南开大学化学生物学系元素有机化学国家重点实验室天津 300071)

收稿日期:2009-08-03 修回日期:2009-09-23 发布日期:2010-04-28
通讯作者: 班树荣 E-mail:shurongban@163.com, banshurong@syn.nankai.edu.cn
基金资助:
国家自然科学基金(No. 20432010);国家重点基础研究发展计划(973计划;No. 2003CB114403); 科技部国际合作项目(2008DFA30770); 教育部科学技术研究重点(重大)项目（No.104189）;山西省青年科学研究基金(2009021041-1)

Synthesis and Bioactivity of N-(5 -Bromo-4 -substituted pyrimidin-2 -yl)phenyl Sulfonylurea

Ban Shurong*^{,1 Niu Congwei² Chen Wenbin² Li Qingshan¹ Xi Zhen*^,2}

(¹ School of Pharmaceutical Science, Shanxi Medical University, Taiyuan 030001)
(²State Key Laboratory of Elemento-Organic Chemistry, Department of Chemical Biology, Nankai University, Tianjin 300071)

Received:2009-08-03 Revised:2009-09-23 Published:2010-04-28

Abstract

Acetohydroxy acid synthase (AHAS) catalyzes the key reactionsin the biosynthesis pathways of branched-chain amino acids (valine,isoleucine and leucine) in plants and microorganisms, and sulfonylurea herbicides are inhibitors of AHAS, characterized by high herbicidal activity, high degree of selectivity, and excellent environmental safety. A series of 5-bromopyrimidinyl-containing new sulfonylureas have been synthesized through bromination of 2-amino-4-methyl pyrimidine, followed by further modification and then coupled with sulfonyl isocyanate. Their structures were confirmed by ¹H NMR, MS techniques and elemental analysis. Preliminary bioassay of sulfonylureas showed that the title compounds exhibited good in vitro activities against E. coli acetohydroxy acid synthase isoenzyme AHASII but showed lower herbicidal activities in vivo, compared with commercial herbicide tribenuron-methly.

Key words: sulfonylurea, 2-amino-4-methyl pyrimidine, bromination, inhibitors of AHAS, herbicidal activity

Cite this article

BAN Shu-Rong, NIU Cong-Wei, CHEN Wen-Ban, LI Jing-Shan, XI Zhen. Synthesis and Bioactivity of N-(5 -Bromo-4 -substituted pyrimidin-2 -yl)phenyl Sulfonylurea[J]. Chin. J. Org. Chem., 2010, 30(04): 564-568.

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N-(5 -溴-4 -取代嘧啶-2 -基)苯磺酰脲化合物的合成和生物活性

Synthesis and Bioactivity of N-(5 -Bromo-4 -substituted pyrimidin-2 -yl)phenyl Sulfonylurea

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