1-(2-氯苯基)环丙烷甲腈 | 122143-18-4

• 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: 1-(2-氯苯基)环丙烷甲腈
• 英文名称: 1-(2-chlorophenyl)cyclopropane-1-carbonitrile
• 英文别名: 1-(2-Chlorophenyl)-cyclopropane-carbonitrile；1-(2'-chlorophenyl)-cyclopropylnitrile；1-(2-Chlorophenyl)cyclopropanecarbonitrile
• CAS: 122143-18-4
• 化学式: C₁₀H₈ClN
• 分子量: 177.633
• InChiKey: QZTBYZDCUXBPLS-UHFFFAOYSA-N

物化性质

• 沸点：
  312.2±35.0 °C(Predicted)
• 密度：
  1.24g/ml

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

安全信息

• 海关编码：
  2926909090
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302
• 储存条件：
  2-8℃

反应信息

• 作为反应物：
  描述：

  1-(2-氯苯基)环丙烷甲腈 在 水 、 lithium hydroxide 作用下， 反应 15.0h， 以90%的产率得到1-(2-氯苯基)环丙烷羧酸
  参考文献：
  名称：

  Discovery of 2-[1-(4-Chlorophenyl)cyclopropyl]-3-hydroxy-8-(trifluoromethyl)quinoline-4-carboxylic Acid (PSI-421), a P-Selectin Inhibitor with Improved Pharmacokinetic Properties and Oral Efficacy in Models of Vascular Injury

  摘要：

  Previously, we reported the discovery of PSI-697 (1a), a C-2 benzyl substituted quinoline salicylic acid-based P-selectin inhibitor. It is active in a variety of animal models of cardiovascular disease. Compound 1a has also been shown to be well tolerated and safe in healthy volunteers at doses of up to 1200 mg in a phase 1 single ascending dose study. However, its oral bioavailability was low. Our goal was to identify a back up compound with equal potency, increased solubility, and increased exposure. We expanded our structure activity-studies in this series by branching at the alpha position of the C-2 benzyl side chain and through modification of substituents on the carboxylic A-ring of the quinoline. This resulted in discovery of PSI-421 with marked improvement in aqueous solubility and pharmacokinetic properties. This compound has shown oral efficacy in animal models of arterial and venous injury and was selected as a preclinical development compound for potential treatment of such diseases as atherosclerosis and deep vein thrombosis.

  DOI：

  10.1021/jm9013696
• 作为产物：
  描述：

  邻氯苯乙腈 、 1-溴-2-氯乙烷 在 苄基三乙基氯化铵 、 sodium hydroxide 作用下， 以 水 为溶剂， 以100%的产率得到1-(2-氯苯基)环丙烷甲腈
  参考文献：
  名称：

  Discovery of 2-[1-(4-Chlorophenyl)cyclopropyl]-3-hydroxy-8-(trifluoromethyl)quinoline-4-carboxylic Acid (PSI-421), a P-Selectin Inhibitor with Improved Pharmacokinetic Properties and Oral Efficacy in Models of Vascular Injury

  摘要：

  Previously, we reported the discovery of PSI-697 (1a), a C-2 benzyl substituted quinoline salicylic acid-based P-selectin inhibitor. It is active in a variety of animal models of cardiovascular disease. Compound 1a has also been shown to be well tolerated and safe in healthy volunteers at doses of up to 1200 mg in a phase 1 single ascending dose study. However, its oral bioavailability was low. Our goal was to identify a back up compound with equal potency, increased solubility, and increased exposure. We expanded our structure activity-studies in this series by branching at the alpha position of the C-2 benzyl side chain and through modification of substituents on the carboxylic A-ring of the quinoline. This resulted in discovery of PSI-421 with marked improvement in aqueous solubility and pharmacokinetic properties. This compound has shown oral efficacy in animal models of arterial and venous injury and was selected as a preclinical development compound for potential treatment of such diseases as atherosclerosis and deep vein thrombosis.

  DOI：

  10.1021/jm9013696

文献信息

• Methods and Compositions for Selectin Inhibition
  申请人：Kaila Neelu

  公开号：US20080255192A1

  公开（公告）日：2008-10-16

  The present teachings relate to novel compounds of formula I: wherein the constituent variables are as defined herein. Compounds of the present teachings can act as antagonists of the mammalian adhesion proteins known as selecting. Methods for treating or preventing selectin-mediated disorders are provided, which include administration of these compounds in a therapeutically effective amount.

  本教学涉及到式I的新化合物： 其中组成变量如本文所定义。本教学的化合物可以作为被称为选择素的哺乳动物粘附蛋白的拮抗剂。提供了治疗或预防选择素介导的疾病的方法，包括以治疗有效剂量给予这些化合物。
• Nonsteroidal antiinflammatory agents
  申请人：——

  公开号：US20020077356A1

  公开（公告）日：2002-06-20

  The compound of formula 1 1 useful in the treatment of inflammation.

  化合物的化学式11在治疗炎症方面很有用。
• The diastereoselective synthesis of 2,3-diaryl-3-cyano-substituted pyrrolidines via the MgI2 mediated ring expansion of aryl cyclopropyl nitriles
  作者：Darren Stead

  DOI：10.1016/j.tetlet.2020.152325

  日期：2020.9

  reaction of aryl substituted cyclopropyl nitriles with tosyl aldimines to give 2,3-diaryl-3-cyano-substituted pyrrolidines has been demonstrated. In all cases, the trans-diastereoisomer was determined to be the major product. The overall yield and diastereoselectivity of the reaction showed some sensitivity to the electronic and steric demands of the aryl cyclopropyl nitriles and the tosyl aldimines

  已经证明了MgI 2介导的芳基取代的环丙基腈与甲苯磺酰基亚胺的反应，得到2，3-二芳基-3-氰基取代的吡咯烷。在所有情况下，反式非对映异构体被确定为主要产物。反应的总收率和非对映选择性显示出对芳基环丙基腈和甲苯磺酰基亚胺的电子和空间要求的敏感性。就产率和非对映选择性而言，在两个反应伙伴上均用吸电子取代基取代被证明是有益的。
• Ortho-substituted benzyl carboxylates and fungicides which contain these
  申请人：BASF Aktiengsellschaft

  公开号：US04952720A1

  公开（公告）日：1990-08-28

  Ortho-substituted benzyl carboxylates of the formula ##STR1## where R.sup.1 is alkoxy, alkylthio, halogen or amino, R.sup.2 is alkoxycarbonyl, cyano or CONH.sub.2, R.sup.3 l is hydrogen, halogen, cyano, aryl, aryloxy, a saturated or unsaturated heterocyclic radical, cycloalkyl, or substituted cyclopropyl, X is alkylene, and n is 0 or 1, and fungicides containing these compounds.

  公式为##STR1##的正位取代苯甲酸苄酯，其中R.sup.1为烷氧基，烷基硫基，卤素或氨基，R.sup.2为烷氧羰基，氰基或CONH.sub.2，R.sup.3为氢，卤素，氰基，芳基，芳基氧基，饱和或不饱和杂环基，环烷基或取代的环丙基，X为烷基，n为0或1，并且含有这些化合物的杀菌剂。
• Ortho-substituierte Carbonsäurebenzylester und Fungizide, die diese Verbindungen enthalten
  申请人：BASF Aktiengesellschaft

  公开号：EP0310954A1

  公开（公告）日：1989-04-12

  Ortho-substituierte Carbonsäure-benzylester der Formel in der R1 Alkoxy, Alkylthio, Halogen oder Amino, R2 Alkoxycarbonyl, Cyano oder CONH2, R3 Wasserstoff, Halogen, Cyano, Aryl, Aryloxy, einen gesättigten oder ungesättigten heterocyclischen Rest, Cycloalkyl oder substituiertes Cyclopropyl, X Alkylen und n 0 oder 1 bedeutet und diese Verbindungen enthaltende Fungizide.

  式中的正代羧酸苄酯 其中 R1 为烷氧基、烷硫基、卤素或氨基、 R2 烷氧基羰基、氰基或 CONH2、 R3 是氢、卤素、氰基、芳基、芳氧基、饱和或不饱和杂环基、环烷基或取代环丙基，X 是亚烷基，n 是 0 或 1，以及含有这些化合物的杀菌剂。