{[2-(2-Cyano-phenylsulfanyl)-benzoyl]-methyl-amino}-acetic acid | 163725-03-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: {[2-(2-Cyano-phenylsulfanyl)-benzoyl]-methyl-amino}-acetic acid
• 英文别名: 2-[[2-(2-Cyanophenyl)sulfanylbenzoyl]-methylamino]acetic acid
• CAS: 163725-03-9
• 化学式: C₁₇H₁₄N₂O₃S
• 分子量: 326.376
• InChiKey: VSKDGCXVFVBBHK-UHFFFAOYSA-N

物化性质

• 沸点：
  543.7±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  {[2-(2-Cyano-phenylsulfanyl)-benzoyl]-methyl-amino}-acetic acid 在 N-甲基吗啉 、 盐酸 、 草酰氯 、 1-羟基苯并三唑 、 二甲基亚砜 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 1,4-二氧六环 、 N,N-二甲基乙酰胺 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and activity studies of conformationally restricted α-ketoamide factor Xa inhibitors

  摘要：

  Conformationally restricted borolysine compounds containing a 2-(2-cyanophenylthio) benzoyl in the P3 position unexpectedly led to enhanced factor Xa inhibition. In an effort to improve both the potency and selectivity of this series by extending into the S' domain, we have replaced the boronic acid with alpha-ketoamides, utilizing a novel process that was developed in our labs. (C) 2000 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00215-8
• 作为产物：
  描述：

  {[2-(2-Cyano-phenylsulfanyl)-benzoyl]-methyl-amino}-acetic acid methyl ester 在 lithium hydroxide 作用下， 以 甲醇 为溶剂， 生成 {[2-(2-Cyano-phenylsulfanyl)-benzoyl]-methyl-amino}-acetic acid
  参考文献：
  名称：

  Synthesis and activity studies of conformationally restricted α-ketoamide factor Xa inhibitors

  摘要：

  Conformationally restricted borolysine compounds containing a 2-(2-cyanophenylthio) benzoyl in the P3 position unexpectedly led to enhanced factor Xa inhibition. In an effort to improve both the potency and selectivity of this series by extending into the S' domain, we have replaced the boronic acid with alpha-ketoamides, utilizing a novel process that was developed in our labs. (C) 2000 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00215-8

文献信息

• The synthesis of lysine α-ketoamide thrombin inhibitord via an epoxy amide ring opening
  作者：Joseph Cacciola、Richard S Alexander、John M Fevig、Pieter F.W Stouten

  DOI：10.1016/s0040-4039(97)01205-7

  日期：1997.8

  We describe a novel route for the preparation of substituted α-ketoamides of lysine. These compounds, due to the presence of an electrophilic carbonyl, display submicromolar activity toward the enzyme thrombin.

  我们描述了一种制备赖氨酸的取代α-酮酰胺的新颖途径。由于存在亲电羰基，这些化合物显示出对酶凝血酶的亚微摩尔活性。
• Synthesis and activity studies of conformationally restricted α-ketoamide factor Xa inhibitors
  作者：Joseph Cacciola、John M. Fevig、Pieter F.W. Stouten、Richard S. Alexander、Robert M. Knabb、Ruth R. Wexler

  DOI：10.1016/s0960-894x(00)00215-8

  日期：2000.6

  Conformationally restricted borolysine compounds containing a 2-(2-cyanophenylthio) benzoyl in the P3 position unexpectedly led to enhanced factor Xa inhibition. In an effort to improve both the potency and selectivity of this series by extending into the S' domain, we have replaced the boronic acid with alpha-ketoamides, utilizing a novel process that was developed in our labs. (C) 2000 DuPont Pharmaceuticals Company. Published by Elsevier Science Ltd. All rights reserved.