Methyl 6-[(4-methoxyphenyl)methylamino]-5-nitro-2-thiophen-2-ylpyrimidine-4-carboxylate | 849703-65-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: Methyl 6-[(4-methoxyphenyl)methylamino]-5-nitro-2-thiophen-2-ylpyrimidine-4-carboxylate
• CAS: 849703-65-7
• 化学式: C₁₈H₁₆N₄O₅S
• 分子量: 400.415
• InChiKey: ORZTXONFKZWDBZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  147
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  Methyl 6-[(4-methoxyphenyl)methylamino]-5-nitro-2-thiophen-2-ylpyrimidine-4-carboxylate 在 盐酸 、 甲酸 、 三氟乙酸 、 锌 作用下， 反应 2.0h， 生成 2-Thiophen-2-yl-9H-purine-6-carboxylic acid methyl ester
  参考文献：
  名称：

  Active site inhibitors of HCV NS5B polymerase. The development and pharmacophore of 2-thienyl-5,6-dihydroxypyrimidine-4-carboxylic acid

  摘要：

  5,6-Dihydroxypyrimidine-4-carboxylic acids are a promising series of hepatitis C virus (HCV) NS5B polymerase inhibitors that bind at the active site of the enzyme. Here we report a simple 2-thienyl substituted analogue that shows 10-fold improved activity over the original lead, and which allowed us to further delineate the key elements of the pharmacophore of this class of inhibitor. This work led to the identification of a trifluoromethyl acylsulfonamide group as a viable replacement for the C4 carboxylic acid in this series. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.075
• 作为产物：
  描述：

  2,6-二氯-5-硝基嘧啶-4-羧酸甲酯 在 bis-triphenylphosphine-palladium(II) chloride 、 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 Methyl 6-[(4-methoxyphenyl)methylamino]-5-nitro-2-thiophen-2-ylpyrimidine-4-carboxylate
  参考文献：
  名称：

  Active site inhibitors of HCV NS5B polymerase. The development and pharmacophore of 2-thienyl-5,6-dihydroxypyrimidine-4-carboxylic acid

  摘要：

  5,6-Dihydroxypyrimidine-4-carboxylic acids are a promising series of hepatitis C virus (HCV) NS5B polymerase inhibitors that bind at the active site of the enzyme. Here we report a simple 2-thienyl substituted analogue that shows 10-fold improved activity over the original lead, and which allowed us to further delineate the key elements of the pharmacophore of this class of inhibitor. This work led to the identification of a trifluoromethyl acylsulfonamide group as a viable replacement for the C4 carboxylic acid in this series. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.07.075

文献信息

• CHEMICAL COMPOUNDS
  申请人：Aspinall Mary Bernadette

  公开号：US20110086759A1

  公开（公告）日：2011-04-14

  The present invention relates to substituted pyrimidine derivatives of as well as N-oxides and agriculturally acceptable salts thereof, and their use to control undesired plant growth, in particular in crops of useful plants. The invention extends to herbicidal compositions comprising such compounds, N-oxides and/or salts as well as mixtures of the same with one or more further active ingredient (such as, for example, an herbicide, fungicide, insecticide and/or plant growth regulator) and/or a safener.

  本发明涉及取代嘧啶衍生物以及其氮氧化物和农业可接受的盐，并用于控制不良植物生长，特别是在有用植物的作物中。该发明还涉及包含这些化合物、氮氧化物和/或盐以及与一种或多种其他活性成分（例如除草剂、杀菌剂、杀虫剂和/或植物生长调节剂）和/或安全剂混合的除草剂组合物。
• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSÉS CHIMIQUES
  申请人：SYNGENTA LTD

  公开号：WO2009081112A2

  公开（公告）日：2009-07-02

  The present invention relates to substituted pyrimidine derivatives of as well as N-oxides and agriculturally acceptable salts thereof, and their use to control undesired plant growth, in particular in crops of useful plants. The invention extends to herbicidal compositions comprising such compounds, N-oxides and/or salts as well as mixtures of the same with one or more further active ingredient (such as, for example, an herbicide, fungicide, insecticide and/or plant growth regulator) and/or a safener.
• Active site inhibitors of HCV NS5B polymerase. The development and pharmacophore of 2-thienyl-5,6-dihydroxypyrimidine-4-carboxylic acid
  作者：Ian Stansfield、Salvatore Avolio、Stefania Colarusso、Nadia Gennari、Frank Narjes、Barbara Pacini、Simona Ponzi、Steven Harper

  DOI：10.1016/j.bmcl.2004.07.075

  日期：2004.10

  5,6-Dihydroxypyrimidine-4-carboxylic acids are a promising series of hepatitis C virus (HCV) NS5B polymerase inhibitors that bind at the active site of the enzyme. Here we report a simple 2-thienyl substituted analogue that shows 10-fold improved activity over the original lead, and which allowed us to further delineate the key elements of the pharmacophore of this class of inhibitor. This work led to the identification of a trifluoromethyl acylsulfonamide group as a viable replacement for the C4 carboxylic acid in this series. (C) 2004 Elsevier Ltd. All rights reserved.