Ethyl (3,3,5,5-tetramethylcyclohexylidene)cyanoacetate | 219811-29-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Ethyl (3,3,5,5-tetramethylcyclohexylidene)cyanoacetate
• 英文别名: ethyl 2-cyano-2-(3,3,5,5-tetramethylcyclohexylidene)acetate
• CAS: 219811-29-7
• 化学式: C₁₅H₂₃NO₂
• 分子量: 249.353
• InChiKey: PRQQYOOUHLGISO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  50.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Ethyl (3,3,5,5-tetramethylcyclohexylidene)cyanoacetate 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 66.0h， 生成 Ethyl 2-(1-cyano-3,3,5,5-tetramethylcyclohexyl)acetate
  参考文献：
  名称：

  Identification of Novel Ligands for the Gabapentin Binding Site on the α₂δ Subunit of a Calcium Channel and Their Evaluation as Anticonvulsant Agents

  摘要：

  As part of a program to investigate the structure-activity relationships of Gabapentin (Neurontin), a number of alkylated analogues were synthesized and evaluated in vitro for binding to the Gabapentin binding site located on the alpha(2) delta subunit of a calcium channel. A number of other bridged and heterocyclic analogues are also reported along with their in vitro data. Two compounds showing higher affinity than Gabapentin were selected for evaluation in an animal model of epilepsy. One of these compounds, cis-(1S,3R)-(1-(aminomethyl)-3-methylcyclohexyl)acetic acid hydrochloride (19), was shown to be effective in this model with a profile similar to that of Gabapentin itself.

  DOI：

  10.1021/jm970649n
• 作为产物：
  描述：

  3,3,5,5-四甲基环己酮 、 氰乙酸乙酯 在 ammonium acetate 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 24.0h， 生成 Ethyl (3,3,5,5-tetramethylcyclohexylidene)cyanoacetate
  参考文献：
  名称：

  Identification of Novel Ligands for the Gabapentin Binding Site on the α₂δ Subunit of a Calcium Channel and Their Evaluation as Anticonvulsant Agents

  摘要：

  As part of a program to investigate the structure-activity relationships of Gabapentin (Neurontin), a number of alkylated analogues were synthesized and evaluated in vitro for binding to the Gabapentin binding site located on the alpha(2) delta subunit of a calcium channel. A number of other bridged and heterocyclic analogues are also reported along with their in vitro data. Two compounds showing higher affinity than Gabapentin were selected for evaluation in an animal model of epilepsy. One of these compounds, cis-(1S,3R)-(1-(aminomethyl)-3-methylcyclohexyl)acetic acid hydrochloride (19), was shown to be effective in this model with a profile similar to that of Gabapentin itself.

  DOI：

  10.1021/jm970649n

文献信息

• 1-Amino-alkylcyclohexane NMDA receptor antagonists
  申请人：Merz + Co. GmbH & Co.

  公开号：US06034134A1

  公开（公告）日：2000-03-07

  Certain 1-aminoalkylcyclohexanes are systemically-active uncompetitive NMDA receptor antagonists having rapid blocking/unblocking kinetics and strong voltage-dependency and are therefore useful in the alleviation of conditions resulting from disturbances of glutamatergic transmission giving them a wide range of utility in the treatment of CNS disorders involving the same, as well as in non-NMDA indications, due to their immunomodulatory, antimalarial, anti-Borna virus, and anti-Hepatitis C activities and utilities. Pharmaceutical compositions thereof and a method-of-treating conditions which are alleviated by the employment of an NMDA receptor antagonist, as well as the aforementioned non-NMDA indications, and a method for the preparation of the active 1-aminoalkylcyclohexane compounds involved.

  某些1-氨基烷基环己烷是系统性活性的非竞争性NMDA受体拮抗剂，具有快速的阻滞/解除动力学和强烈的电压依赖性，因此在缓解由谷氨酸能传递干扰引起的病症方面具有广泛的用途，包括在涉及相同情况的中枢神经系统疾病的治疗中，以及在非NMDA适应症中，由于它们的免疫调节，抗疟疾，抗Borna病毒和抗丙型肝炎活性和用途。其中的制药组合物和治疗使用NMDA受体拮抗剂缓解的病症的方法，以及前述的非NMDA适应症和涉及的活性1-氨基烷基环己烷化合物的制备方法。
• 1-amino-alkylcyclohexane NMDA receptor antagonists
  申请人：Merz + Co. GmbH & Co.

  公开号：US06071966A1

  公开（公告）日：2000-06-06

  Certain 1-aminoalkylcyclohexanes are systemically-active uncompetitive NMDA receptor antagonists having rapid blocking/unblocking kinetics and strong voltage-dependency and are therefore useful in the alleviation of conditions resulting from disturbances of glutamatergic transmission giving them a wide range of utility in the treatment of CNS disorders involving the same, as well as in non-NMDA indications, due to their immunomodulatory, antimalarial, anti-Borna virus, and anti-Hepatitis C activities and utilities. Pharmaceutical compositions thereof and a method-of-treating conditions which are alleviated by the employment of an NMDA receptor antagonist, as well as the aforementioned non-NMDA indications, and a method for the preparation of the active 1-aminoalkylcyclohexane compounds involved.

  某些1-氨基烷基环己烷是系统活性的非竞争性NMDA受体拮抗剂，具有快速的阻断/解除阻断动力学和强烈的电压依赖性，因此在缓解由谷氨酸能传递干扰引起的病症方面具有广泛的应用价值，同时也具有免疫调节、抗疟疾、抗波纳病毒和抗丙型肝炎活性和用途，因此在治疗涉及相同疾病的中枢神经系统疾病以及非NMDA适应症方面具有广泛的用途。其中的制药组合物和治疗使用NMDA受体拮抗剂缓解的病症的方法，以及前述的非NMDA适应症和涉及的活性1-氨基烷基环己烷化合物的制备方法。
• Combination therapy using 1-aminocyclohexane derivatives and acetylcholinesterase and inhibitors
  申请人：Moebius Hans-Joerg

  公开号：US20090124659A1

  公开（公告）日：2009-05-14

  The invention relates to a novel drug combination therapy useful in the treatment of dementia comprising administering an 1-aminocyclohexane derivative such as memantine or neramexane and an acetylcholinesterase inhibitor (AChEI) such as galantamine, tacrine, donepezil, or rivastigmine.

  本发明涉及一种新型药物组合疗法，用于治疗痴呆症，包括给予1-氨基环己烷衍生物，如美金刚烷或内拉美昔，并且给予乙酰胆碱酯酶抑制剂（AChEI），如加兰他敏、他克林、多奈哌齐或利他林。
• Combination therapy using 1-aminocyclohexane derivatives and acetylcholinesterase inhibitors
  申请人：Moebius Hans-Joerg

  公开号：US20100227852A1

  公开（公告）日：2010-09-09

  The invention relates to a novel drug combination therapy useful in the treatment of dementia comprising administering an 1-aminocyclohexane derivative such as memantine or neramexane and an acetylcholinesterase inhibitor (AChEI) such as galantamine, tacrine, donepezil, or rivastigmine.

  本发明涉及一种新型药物组合疗法，用于治疗痴呆症，包括给予1-氨基环己烷衍生物，如美金刚或奈拉美昔，以及乙酰胆碱酯酶抑制剂（AChEI），如加兰他敏，他克林，多奈哌齐或利伐替珀。
• COMBINATION THERAPY USING 1-AMINOCYCLOHEXANE DERIVATIVES AND ACETYLCHOLINESTERASE INHIBITORS
  申请人：MERZ PHARMA GmbH & CO. KGaA

  公开号：US20140371260A1

  公开（公告）日：2014-12-18

  The invention relates to a novel drug combination therapy useful in the treatment of dementia comprising administering an 1-aminocyclohexane derivative such as memantine or neramexane and an acetylcholinesterase inhibitor (AChEI) such as galantamine, tacrine, donepezil, or rivastigmine.

  本发明涉及一种新型药物组合疗法，用于治疗痴呆症，包括给予1-氨基环己烷衍生物，如美金刚烷或尼拉美昔，以及乙酰胆碱酯酶抑制剂（AChEI），如加兰他敏、他克林、多奈哌齐或利伐他汀。