N-[(4-chloro-phenoxy)-acetyl]-N-phenyl-glycine | 130831-41-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-[(4-chloro-phenoxy)-acetyl]-N-phenyl-glycine
• 英文别名: N-[(4-Chlor-phenoxy)-acetyl]-N-phenyl-glycin；2-(N-[2-(4-chlorophenoxy)acetyl]anilino)acetic acid
• CAS: 130831-41-3
• 化学式: C₁₆H₁₄ClNO₄
• 分子量: 319.744
• InChiKey: WUMUHJIDEHPVIA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  66.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-[(4-chloro-phenoxy)-acetyl]-N-phenyl-glycine 、 甲胺 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 作用下， 反应 0.5h， 以91 mg的产率得到2-(4-chlorophenoxy)-N-(2-(methylamino)-2-oxoethyl)-N-phenylacetamide
  参考文献：
  名称：

  Discovery of Indoline-2-carboxamide Derivatives as a New Class of Brain-Penetrant Inhibitors of Trypanosoma brucei

  摘要：

  There is an urgent need for new, brain penetrant small molecules that target the central nervous system second stage of human African trypanosomiasis (HAT). We report that a series of novel indoline-2carboxamides have been identified as inhibitors of Trypanosoma brucei from screening of a focused protease library against Trypanosoma brucei brucei in culture. We describe the optimization and characterization of this series. Potent antiproliferative activity was observed. The series demonstrated excellent pharmacokinetic properties, full cures in a stage 1 mouse model of HAT, and a partial cure in a stage 2 mouse model of HAT. Lack of tolerability prevented delivery of a fully curative regimen in the stage 2 mouse model and thus further progress of this series.

  DOI：

  10.1021/acs.jmedchem.5b00596
• 作为产物：
  描述：

  对氯苯氧乙酸 、 N-苯基甘氨酸 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 作用下， 以 二氯甲烷 为溶剂， 反应 2.5h， 生成 N-[(4-chloro-phenoxy)-acetyl]-N-phenyl-glycine
  参考文献：
  名称：

  Discovery of Indoline-2-carboxamide Derivatives as a New Class of Brain-Penetrant Inhibitors of Trypanosoma brucei

  摘要：

  There is an urgent need for new, brain penetrant small molecules that target the central nervous system second stage of human African trypanosomiasis (HAT). We report that a series of novel indoline-2carboxamides have been identified as inhibitors of Trypanosoma brucei from screening of a focused protease library against Trypanosoma brucei brucei in culture. We describe the optimization and characterization of this series. Potent antiproliferative activity was observed. The series demonstrated excellent pharmacokinetic properties, full cures in a stage 1 mouse model of HAT, and a partial cure in a stage 2 mouse model of HAT. Lack of tolerability prevented delivery of a fully curative regimen in the stage 2 mouse model and thus further progress of this series.

  DOI：

  10.1021/acs.jmedchem.5b00596

文献信息

• Phenoxyacetylamide derivative and process for production and use thereof
  申请人：SUNTORY LIMITED

  公开号：EP0205327A1

  公开（公告）日：1986-12-17

  Phenoxyacetylamide derivative and salt thereof, a process for production thereof comprising acylation of amino acid or derivative thereof, a herbicidal composition comprising the compound, and a method for killing or controlling plants using the compound. The compounds have a selective herbicidal effect. These compounds have the following formula: wherein, R' represents a hydrogen atom or an alkyl group R2 represents a halogen atom; and A represents 1, 5-dicarboxypentyl group, 1,4-dicarboxybutyl group, carboxymethyl group, 1-carboxy-1-phenylmethyl group, 1-carboxypropyl group, 3-carboxypropyl group, 1-carboxy-2-ethanol group, 1-carboxy-3-propanol group, 1-carboxyethyl group, 1-carboxypentyl group, 1-carboxybutyl group or 1-carboxyheptyl group, or a group wherein, R3 represents a hydrogen atom; a branched chain alkyl group optionally substituted by a hydroxyl group; or a straight-chain alkyl group substituted by ethylene group, epoxy group, nitroguanidino group or by cycloalkyl group; and B represents a formyl group, hydroxymethyl group, carboxyl group or an alkylcarboxylic acid ester group; or R1 and R3, together with the nitrogen atom to which R' bonds and the carbon atom to which R3 bonds, form a ring structure; with a proviso that at least one of R' and R3 represents a group other than a hydrogen atom.

  苯氧乙酰胺衍生物及其盐、包括氨基酸或其衍生物酰化的生产工艺、包含该化合物的除草组合物，以及使用该化合物杀死或控制植物的方法。这些化合物具有选择性除草作用。这些化合物具有下式： 其中 R' 代表氢原子或烷基 R2 代表卤素原子；以及 A 代表 1，5-二羧基戊基、 1,4-二羧基丁基 1-羧基-1-苯基甲基，1-羧基丙基 3-羧丙基、1-羧基-2-乙醇基、 1-羧基-2-乙醇基、1-羧基-3-丙醇基、1-羧基乙基 1-羧基戊基、1-羧基丁基或 1-羧基庚基或一个基团 其中 R3 代表氢原子；任选被羟基取代的支链烷基；或被乙烯基、环氧基、硝基胍基或环烷基取代的直链烷基；和 B 代表甲酰基、羟甲基、羧基或烷基羧酸酯基；或 R1 和 R3 与 R' 键合的氮原子和 R3 键合的碳原子一起形成环状结构； 但 R' 和 R3 中至少有一个代表氢原子以外的基团。
• Notes - N-Aroxyacetyl -N-arylglycines
  作者：Akira Takeda

  DOI：10.1021/jo01095a600

  日期：1958.1