Methyl 3-chloro-2-[(5-methoxy-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate | 1242652-21-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 英文名称: Methyl 3-chloro-2-[(5-methoxy-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate
• 英文别名: methyl 3-chloro-2-[(5-methoxy-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate
• CAS: 1242652-21-6
• 化学式: C₁₄H₁₂ClN₅O₅S
• 分子量: 397.799
• InChiKey: NQEJFIHDFYIORP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  133
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  5-methoxy-1,2,4-triazolo[1,5-a]pyrimidine-2-sulfonyl chloride 、 2-氨基-3-氯苯甲酸甲酯 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 Methyl 3-chloro-2-[(5-methoxy-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)sulfonylamino]benzoate
  参考文献：
  名称：

  Syntheses and herbicidal activity of new triazolopyrimidine-2-sulfonamides as acetohydroxyacid synthase inhibitor

  摘要：

  The triazolopyrimidine-2-sulfonanilide, discovered from preparing bioisosteres of the sulfonylurea herbicides, is an important class of acetohydroxyacid synthase (AHAS, EC 4.1.3.18) inhibitors. At least over ten triazolopyrimidine sulfonanilides have been commercialized as herbicides for the control of broadleaf weeds and grass with cereal crop selectivity. Herein, a series of triazolopyrimidine-2-sulfonanilides were designed and synthesized with the aim of discovery of new herbicides with higher activity. The assay results of the inhibition activity of the synthesized compounds against Arabidopsis thatiana AHAS indicated that some compounds showed a little higher activity against flumetsulam (FS), the first commercial triazolopyrimidine-2-sulfonanilide-type herbicide. The k(i) values of two promising compounds 3d and 8h are respectively, 1.61 and 1.29 mu M, while that of FS is 1.85 mu M. Computational simulation results indicated the ester group of compound 3d formed hydrogen bonds with the surrounding residues Arg'198 and Ser653, which accounts for its 11.5-folds higher AHAS inhibition activity than Y6610. Further green house assay showed that compound 3d has comparable herbicidal activity as FS. Even at the concentration of 37.5 g.ai/ha, 3d showed excellent herbicidal activity against Galium aparine, Cerastium arvense, Chenopodium album, Amaranthus retroflexus, and R mu mex acetasa, moderate herbicidal activity against Polygonum humifusum, Cyperus iria, and Eclipta prostrate. The combination of in vitro and in vivo assay indicated that 3d could be regarded as a new potential acetohydroxyacid synthase-inhibiting herbicide candidate for further study. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.015

文献信息

• Syntheses and herbicidal activity of new triazolopyrimidine-2-sulfonamides as acetohydroxyacid synthase inhibitor
  作者：Chao-Nan Chen、Qiong Chen、Yu-Chao Liu、Xiao-Lei Zhu、Cong-Wei Niu、Zhen Xi、Guang-Fu Yang

  DOI：10.1016/j.bmc.2010.06.015

  日期：2010.7

  The triazolopyrimidine-2-sulfonanilide, discovered from preparing bioisosteres of the sulfonylurea herbicides, is an important class of acetohydroxyacid synthase (AHAS, EC 4.1.3.18) inhibitors. At least over ten triazolopyrimidine sulfonanilides have been commercialized as herbicides for the control of broadleaf weeds and grass with cereal crop selectivity. Herein, a series of triazolopyrimidine-2-sulfonanilides were designed and synthesized with the aim of discovery of new herbicides with higher activity. The assay results of the inhibition activity of the synthesized compounds against Arabidopsis thatiana AHAS indicated that some compounds showed a little higher activity against flumetsulam (FS), the first commercial triazolopyrimidine-2-sulfonanilide-type herbicide. The k(i) values of two promising compounds 3d and 8h are respectively, 1.61 and 1.29 mu M, while that of FS is 1.85 mu M. Computational simulation results indicated the ester group of compound 3d formed hydrogen bonds with the surrounding residues Arg'198 and Ser653, which accounts for its 11.5-folds higher AHAS inhibition activity than Y6610. Further green house assay showed that compound 3d has comparable herbicidal activity as FS. Even at the concentration of 37.5 g.ai/ha, 3d showed excellent herbicidal activity against Galium aparine, Cerastium arvense, Chenopodium album, Amaranthus retroflexus, and R mu mex acetasa, moderate herbicidal activity against Polygonum humifusum, Cyperus iria, and Eclipta prostrate. The combination of in vitro and in vivo assay indicated that 3d could be regarded as a new potential acetohydroxyacid synthase-inhibiting herbicide candidate for further study. (C) 2010 Elsevier Ltd. All rights reserved.