2-(4-氯苯基)乙酰基氰化物 | 924633-52-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(4-氯苯基)乙酰基氰化物
• 英文名称: α-oxo-(4-chlorobenzene)propanenitrile
• 英文别名: 2-(4-Chlorophenyl)acetyl cyanide
• CAS: 924633-52-3
• 化学式: C₉H₆ClNO
• 分子量: 179.606
• InChiKey: NBGUJKMGQRRXFN-UHFFFAOYSA-N

物化性质

• 沸点：
  298.5±23.0 °C(Predicted)
• 密度：
  1.271±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  40.9
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2926909090

反应信息

• 作为反应物：
  描述：

  2-(4-氯苯基)乙酰基氰化物 在 盐酸 、 氢氧化钾 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 19.17h， 生成 3-Benzamido-2-[(4-chlorophenyl)methyl]-7,8,9,10-tetrahydrobenzo[h]quinoline-4-carboxylic acid
  参考文献：
  名称：

  2-(4-Chlorobenzyl)-3-hydroxy-7,8,9,10-tetrahydrobenzo[H]quinoline-4-carboxylic Acid (PSI-697):  Identification of a Clinical Candidate from the Quinoline Salicylic Acid Series of P-Selectin Antagonists

  摘要：

  P-selectin-PSGL-1 interaction causes rolling of leukocytes on the endothelial cell surface, which subsequently leads to firm adherence and leukocyte transmigration through the vessel wall into the surrounding tissues. P-selectin is upregulated on the surface of both platelets and endothelium in a variety of atherosclerosis-associated conditions. Consequently, inhibition of this interaction by means of a small molecule P-selectin antagonist is an attractive strategy for the treatment of atherosclerosis. High-throughput screening and subsequent analoging had led to the identification of compound 1 as the lead candidate. Herein, we report the continuation of this work and the discovery of a second-generation series, the tetrahydrobenzoquinoline salicylic acids. These compounds have improved pharmacokinetic properties, and a number of them have shown oral efficacy in mouse and rat models of atherogenesis and vascular injury. The lead 31 (PSI-697), is currently in clinical development for the treatment of atherothrombotic vascular events.

  DOI：

  10.1021/jm060631p
• 作为产物：
  描述：

  对氯苯乙酸 在 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 生成 2-(4-氯苯基)乙酰基氰化物
  参考文献：
  名称：

  2-(4-Chlorobenzyl)-3-hydroxy-7,8,9,10-tetrahydrobenzo[H]quinoline-4-carboxylic Acid (PSI-697):  Identification of a Clinical Candidate from the Quinoline Salicylic Acid Series of P-Selectin Antagonists

  摘要：

  P-selectin-PSGL-1 interaction causes rolling of leukocytes on the endothelial cell surface, which subsequently leads to firm adherence and leukocyte transmigration through the vessel wall into the surrounding tissues. P-selectin is upregulated on the surface of both platelets and endothelium in a variety of atherosclerosis-associated conditions. Consequently, inhibition of this interaction by means of a small molecule P-selectin antagonist is an attractive strategy for the treatment of atherosclerosis. High-throughput screening and subsequent analoging had led to the identification of compound 1 as the lead candidate. Herein, we report the continuation of this work and the discovery of a second-generation series, the tetrahydrobenzoquinoline salicylic acids. These compounds have improved pharmacokinetic properties, and a number of them have shown oral efficacy in mouse and rat models of atherogenesis and vascular injury. The lead 31 (PSI-697), is currently in clinical development for the treatment of atherothrombotic vascular events.

  DOI：

  10.1021/jm060631p

文献信息

• Novel alpha-cyano-beta-oxopropionamides
  申请人：CIBA-GEIGY AG

  公开号：EP0372470A2

  公开（公告）日：1990-06-13

  -(Substituted carbamoyl)-β-aryl- and heteroaryl-β-oxopropionitriles of formula enol ethers thereof and salts thereof, as well as pharmaceutical preparations containing same and methods of preparing and using these compounds are disclosed. Said compounds represent novel antiinflammatory and antirheumatic agents. Their property to interfere with both the cyclooxygenase and lipoxygenase pathway of the arachidonic fatty acid bioconversion to inflammatory mediators make them valuable therapeutics. These properties render the mentioned substituted carbamoyl-β-oxopropionitriles useful for the treatment of arthritic and rheumatic diseases and other inflammatory conditions in mammals.

  式中的-(取代氨基甲酰基)-β-芳基-和杂芳基-β-氧代丙腈 公开了这些化合物的烯醇醚及其盐类，以及含有这些化合物的药物制剂和制备及使用这些化合物的方法。上述化合物是新型抗炎药和抗风湿药。它们具有干扰环氧化酶和脂氧合酶将花生四烯酸脂肪酸生物转化为炎症介质的途径的特性，使其成为有价值的治疗药物。这些特性使上述取代的氨基甲酰-β-氧代丙腈类化合物可用于治疗哺乳动物的关节炎、风湿病和其他炎症。
• PLANTS HAVING INCREASED TOLERANCE TO HERBICIDES
  申请人：BASF SE

  公开号：EP2992090A2

  公开（公告）日：2016-03-09
• US4224226A
  申请人：——

  公开号：US4224226A

  公开（公告）日：1980-09-23
• US4228082A
  申请人：——

  公开号：US4228082A

  公开（公告）日：1980-10-14
• 2-(4-Chlorobenzyl)-3-hydroxy-7,8,9,10-tetrahydrobenzo[<i>H</i>]quinoline-4-carboxylic Acid (PSI-697):  Identification of a Clinical Candidate from the Quinoline Salicylic Acid Series of P-Selectin Antagonists
  作者：Neelu Kaila、Kristin Janz、Adrian Huang、Alessandro Moretto、Silvano DeBernardo、Patricia W. Bedard、Steve Tam、Valerie Clerin、James C. Keith、Desirée H. H. Tsao、Natalia Sushkova、Gray D. Shaw、Raymond T. Camphausen、Robert G. Schaub、Qin Wang

  DOI：10.1021/jm060631p

  日期：2007.1.1

  P-selectin-PSGL-1 interaction causes rolling of leukocytes on the endothelial cell surface, which subsequently leads to firm adherence and leukocyte transmigration through the vessel wall into the surrounding tissues. P-selectin is upregulated on the surface of both platelets and endothelium in a variety of atherosclerosis-associated conditions. Consequently, inhibition of this interaction by means of a small molecule P-selectin antagonist is an attractive strategy for the treatment of atherosclerosis. High-throughput screening and subsequent analoging had led to the identification of compound 1 as the lead candidate. Herein, we report the continuation of this work and the discovery of a second-generation series, the tetrahydrobenzoquinoline salicylic acids. These compounds have improved pharmacokinetic properties, and a number of them have shown oral efficacy in mouse and rat models of atherogenesis and vascular injury. The lead 31 (PSI-697), is currently in clinical development for the treatment of atherothrombotic vascular events.