2-(Acetyloxy)-N-(3-amino-2-chloro-5-cyanophenyl)acetamide | 133568-80-6

• 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-(Acetyloxy)-N-(3-amino-2-chloro-5-cyanophenyl)acetamide
• 英文别名: [2-(3-amino-2-chloro-5-cyanoanilino)-2-oxoethyl] acetate
• CAS: 133568-80-6
• 化学式: C₁₁H₁₀ClN₃O₃
• 分子量: 267.672
• InChiKey: DBBUDBBAIHNZJC-UHFFFAOYSA-N

物化性质

• 沸点：
  489.8±45.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(Acetyloxy)-N-(3-amino-2-chloro-5-cyanophenyl)acetamide 在 ammonium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以83%的产率得到N-(3-氨基-2-氯-5-氰基苯基)-2-羟基乙酰胺
  参考文献：
  名称：

  Novel antiallergic and antiinflammatory agents. Part I: Synthesis and pharmacology of glycolic amide derivatives

  摘要：

  A series of mono-glycoloylamino derivatives was synthesized by treatment of the corresponding aromatic monoamine derivatives with glycoloyl chloride derivatives in pyridine or dichloromethane, in the presence of a base such as triethylamine or pyridine. Hydrolysis of acetoxy compounds in aqueous ammonia and methanol solution produced hydroxy derivatives with ease. These compounds were tested in the rat PCA (passive cutaneous anaphylaxis) assay by oral administration. Thiazole and thiadiazole derivatives showed moderate inhibition in this assay. In contrast, benzothiazole and benzonitrile derivatives exhibited marked inhibition. In particular, compound 5t also showed marked inhibition of eosinophil adhesion to TNF (tumor necrosis factor) -alpha-treated HUVEC (human umbilical vein endothelial cells) in the range of 10(-8)-10(-5) M. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00065-0
• 作为产物：
  描述：

  3,5-二氨基-4-氯苯甲腈 、 乙酰氧基乙酰氯 在 sodium hydroxide 作用下， 以 乙醚 为溶剂， 反应 0.25h， 以45%的产率得到2-(Acetyloxy)-N-(3-amino-2-chloro-5-cyanophenyl)acetamide
  参考文献：
  名称：

  Novel antiallergic and antiinflammatory agents. Part I: Synthesis and pharmacology of glycolic amide derivatives

  摘要：

  A series of mono-glycoloylamino derivatives was synthesized by treatment of the corresponding aromatic monoamine derivatives with glycoloyl chloride derivatives in pyridine or dichloromethane, in the presence of a base such as triethylamine or pyridine. Hydrolysis of acetoxy compounds in aqueous ammonia and methanol solution produced hydroxy derivatives with ease. These compounds were tested in the rat PCA (passive cutaneous anaphylaxis) assay by oral administration. Thiazole and thiadiazole derivatives showed moderate inhibition in this assay. In contrast, benzothiazole and benzonitrile derivatives exhibited marked inhibition. In particular, compound 5t also showed marked inhibition of eosinophil adhesion to TNF (tumor necrosis factor) -alpha-treated HUVEC (human umbilical vein endothelial cells) in the range of 10(-8)-10(-5) M. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00065-0

文献信息

• Novel antiallergic and antiinflammatory agents. Part II: Synthesis and pharmacology of TYB-2285 and its related compounds
  作者：Masakazu Ban、Hiroaki Taguchi、Takeo Katsushima、Mitsuru Takahashi、Kiyotaka Shinoda、Akihiko Watanabe、Takanari Tominaga

  DOI：10.1016/s0968-0896(98)00066-2

  日期：1998.7

  chloride derivatives in pyridine. Hydrolysis of acetyl compounds gave hydroxy derivatives, from which other acyl derivatives could be synthesized. These compounds were tested in the rat PCA (passive cutaneous anaphylaxis) assay by oral administration. Benzonitrile derivatives (4c, 5c, 6c, 4h, 5h) exhibited notable inhibition in this assay. Compounds 5c and 6c also showed remarkable inhibition of eosinophil

  通过在吡啶中用乙醇酰氯衍生物处理相应的间二氨基苯衍生物，合成了一系列间二（糖基氨基）苯衍生物。乙酰基化合物的水解产生羟基衍生物，从中可以合成其他酰基衍生物。这些化合物在口服PCA（被动性皮肤过敏反应）试验中进行了测试。苯甲腈衍生物（4c，5c，6c，4h，5h）在该试验中表现出显着的抑制作用。化合物5c和6c在10（-8）-10（-5）M的范围内也显示出嗜酸性粒细胞对TNF-（肿瘤坏死因子）α处理的HUVEC（人脐静脉内皮细胞）粘附的显着抑制。化合物5c是目前正在日本进行TYB-2285（图1）研究，用于II期临床研究中的哮喘和特应性皮炎。
• Pharmaceutical composition for suppressing infiltration of eosinophils
  申请人：Toyo Boseki Kabushiki Kaisha

  公开号：EP0687468A2

  公开（公告）日：1995-12-20

  . A pharmaceutical composition for suppressing infiltration of eosinophils, comprising, as an active ingredient, a benzonitrile derivative of the formula (I) wherein R1 is a hydrogen atom, a lower alkyl having 1 to 6 carbon atoms or an acyl having 2 to 10 carbon atoms, and R2 is a hydrogen atom or a halogen atom, and a method for suppressing infiltration of eosinophils, comprising administering said benzonitrile derivative. The compound of the formula (I) inhibits adhesion of eosinophils to vascular endothelial cells and strongly suppresses infiltration of eosinophils into inflammatory lesions. Accordingly, the compound of the formula (I) can be used as an antiinflammatory agent for the prophylaxis and treatment of various diseases associated with infiltration of eosinophils.

  .一种抑制嗜酸性粒细胞浸润的药物组合物，其活性成分包括式 (I) 的苯甲腈衍生物 其中 R1 是氢原子、具有 1 至 6 个碳原子的低级烷基或具有 2 至 10 个碳原子的酰基，R2 是氢原子或卤素原子，以及一种抑制嗜酸性粒细胞浸润的方法，包括施用所述苯腈衍生物。式（I）化合物可抑制嗜酸性粒细胞对血管内皮细胞的粘附，并强烈抑制嗜酸性粒细胞对炎症病灶的浸润。因此，式（I）化合物可用作预防和治疗与嗜酸性粒细胞浸润有关的各种疾病的抗炎剂。
• JPH02311450A
  申请人：——

  公开号：JPH02311450A

  公开（公告）日：1990-12-27
• JPH083036A
  申请人：——

  公开号：JPH083036A

  公开（公告）日：1996-01-09