(4-piperidinylidene)-3-pyridylacetonitrile | 137075-23-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: (4-piperidinylidene)-3-pyridylacetonitrile
• 英文别名: (4-piperidinylidene)-pyridin-3-ylacetonitrile；2-Piperidin-4-ylidene-2-pyridin-3-ylacetonitrile
• CAS: 137075-23-1
• 化学式: C₁₂H₁₃N₃
• 分子量: 199.255
• InChiKey: RKWYXZILWMLPPF-UHFFFAOYSA-N

物化性质

• 沸点：
  393.2±42.0 °C(Predicted)
• 密度：
  1.127±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  48.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3,3-二苯基丙酸 、 (4-piperidinylidene)-3-pyridylacetonitrile 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以75%的产率得到哌啶,4-(氰基-3-吡啶基亚甲基)-1-(1-羰基-3,3-二苯基丙基)-
  参考文献：
  名称：

  (Pyridylcyanomethyl)piperazines as orally active PAF antagonists

  摘要：

  A series of (pyridylcyanomethyl)piperazines was prepared and evaluated for PAF-antagonist activity. Compounds were tested in vitro in a PAF-induced platelet aggregation assay and in vivo in a PAF-induced hypotension test in normotensive rats. Oral activity was ascertained through a PAF-induced mortality test in mice. The main structure-activity trends of the series were established. Activity was mainly found in four skeletons: 1-acyl-4-(3-pyridylcyanomethyl)-piperazine, 1-acyl-4-(4-pyridylcyanomethyl)piperazine, 1-acyl-4-(3-pyridylcyanomethyl)piperidine, and 1-acyl-4-cyano-4-(3-pyridylamino)piperidine. The acyl substituents, diphenylacetyl and 3,3-diphenylpropionyl, provided the most active compounds, and the introduction of an amine or hydroxy group in the 3,3-diphenylpropionyl substituent led to further improvement in oral activity. As a result, three of the most active compounds (100, 114, and 115) have been selected for further pharmacological development.

  DOI：

  10.1021/jm00100a018
• 作为产物：
  描述：

  3-吡啶乙腈 在 三甲基氯硅烷 、 sodium ethanolate 、 sodium iodide 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 49.0h， 生成 (4-piperidinylidene)-3-pyridylacetonitrile
  参考文献：
  名称：

  (Pyridylcyanomethyl)piperazines as orally active PAF antagonists

  摘要：

  A series of (pyridylcyanomethyl)piperazines was prepared and evaluated for PAF-antagonist activity. Compounds were tested in vitro in a PAF-induced platelet aggregation assay and in vivo in a PAF-induced hypotension test in normotensive rats. Oral activity was ascertained through a PAF-induced mortality test in mice. The main structure-activity trends of the series were established. Activity was mainly found in four skeletons: 1-acyl-4-(3-pyridylcyanomethyl)-piperazine, 1-acyl-4-(4-pyridylcyanomethyl)piperazine, 1-acyl-4-(3-pyridylcyanomethyl)piperidine, and 1-acyl-4-cyano-4-(3-pyridylamino)piperidine. The acyl substituents, diphenylacetyl and 3,3-diphenylpropionyl, provided the most active compounds, and the introduction of an amine or hydroxy group in the 3,3-diphenylpropionyl substituent led to further improvement in oral activity. As a result, three of the most active compounds (100, 114, and 115) have been selected for further pharmacological development.

  DOI：

  10.1021/jm00100a018

文献信息

• (cyanomethyl)pyridines useful as PAF antagonists
  申请人：J. URIACH & CIA. S.A.

  公开号：EP0441226A1

  公开（公告）日：1991-08-14

  57 The present invention relates to new (cyanomethyl)pyridines of general formula I: wherein A is nitrogen and B is -CH-, or B is nitrogen and A is -CH-; the group Y-W- represents a group of formula N-CR1(CN)-, N-CH2-CH(CN)-, CH-CH(CN)- or C=C(CN)- wherein R1 is hydrogen or a C1-C6 alkyl group; R represents a group of formula R2CO-, R3R4N-(CH2)nCO- or R5-(CH2)m wherein R2 represents C1-C15 alkyl, aryl, aryl-(C1-C6)-alkyl, aryl-(C1-C6)-alkenyl, diaryl-(C1-C6)-alkyl, diaryl-(C1-C6)-alkenyl, arylhydroxy-(C1-C6)-alkyl, diarylhydroxy-(Ci-C6)-alkyl, aryl-(C1-C6)-alkoxy, diaryl-(C1-C6)-alkoxy, or heteroaryl-(C1-C6)-alkyl group; n is 0, 1, 2 or 3; R3 is hydrogen, C1-C6 alkyl, aryl or aryl-(Cl-C6)-alkyl group; R4 is C3-C6 cycloalkyl, aryl, aryl-(C1-C6)-alkyl, diaryl-(C1-C6)-alkyl, aryl-(C1-C6)-alkylcarbonyl or diaryl-(C1-C6)-alkylcarbonyl group; m is 0, 1 or 2; and R5 is aryl-(C1-C6)-alkyl, diaryl-(C1-C6)-alkyl, diaryl-(C1-C6)-alkylcarbonylamino or diaryl-(C1-C6)-alkylaminocarbonyl group. These compounds are potent, orally active PAF antagonists and consequently, useful in the treatment of the diseases in which this substance is involved.

  本发明涉及一般式I的新(氰甲基)吡啶：其中A为氮，B为-CH-，或者B为氮，A为-CH-；基团Y-W-表示一种具有以下式N-CR1(CN)-、N-CH2-CH(CN)-、CH-CH(CN)-或C=C(CN)-的基团，其中R1为氢或C1-C6烷基；R表示一种具有以下式R2CO-、R3R4N-(CH2)nCO-或R5-(CH2)m的基团，其中R2表示C1-C15烷基、芳基、芳基-(C1-C6)-烷基、芳基-(C1-C6)-烯基、二芳基-(C1-C6)-烷基、二芳基-(C1-C6)-烯基、芳基羟基-(C1-C6)-烷基、二芳基羟基-(Ci-C6)-烷基、芳基-(C1-C6)-氧基、二芳基-(C1-C6)-氧基或杂芳基-(C1-C6)-烷基；n为0、1、2或3；R3为氢、C1-C6烷基、芳基或芳基-(Cl-C6)-烷基；R4为C3-C6环烷基、芳基、芳基-(C1-C6)-烷基、二芳基-(C1-C6)-烷基、芳基-(C1-C6)-烷基羰基或二芳基-(C1-C6)-烷基羰基；m为0、1或2；R5为芳基-(C1-C6)-烷基、二芳基-(C1-C6)-烷基、二芳基-(C1-C6)-烷基羰胺基或二芳基-(C1-C6)-烷基氨基羰基基团。这些化合物是有效的口服PAF拮抗剂，因此，在这种物质参与的疾病治疗中非常有用。
• [EN] SUBSTITUTED INDOLE AND AZAINDOLE OXOACETYL PIPERAZINAMIDE DERIVATIVES<br/>[FR] DÉRIVÉS D'OXOACÉTYL PIPÉRAZINAMIDE À SUBSTITUTION INDOLE ET AZAINDOLE
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2012019003A1

  公开（公告）日：2012-02-09

  Compounds having drug and bio-affecting properties are described herein, including their properties, pharmaceutical compositions and methods of use. In particular, tricyclic aryl or heteroaryl piperazine diamide derivatives that possess unique antiviral activity are set forth. These compounds are useful for the treatment of HIV and AIDS. The compounds herein have the general Formula I:(Formula I should be inserted here) wherein: Y is selected from the group of indole or azaindole systems:(Formula Y should be inserted here) and Z is selected from the group of:(Formula Z should be inserted here)

  本文描述了具有药物和生物影响特性的化合物，包括它们的特性、制药组合物和使用方法。特别地，本文提出了具有独特抗病毒活性的三环芳基或杂芳基哌嗪二酰胺衍生物。这些化合物对于治疗艾滋病毒和艾滋病非常有用。本文中的化合物具有一般公式I：(应在此处插入公式I) 其中：Y选自吲哚或氮杂吲哚系统的群体中：(应在此处插入公式Y) 而Z选自以下群体中：(应在此处插入公式Z)
• SUBSTITUTED INDOLE AND AZAINDOLE OXOACETYL PIPERAZINAMIDE DERIVATIVES
  申请人：Wang Tao

  公开号：US20120202775A1

  公开（公告）日：2012-08-09

  Compounds having drug and bio-affecting properties are described herein, including their properties, pharmaceutical compositions and methods of use. In particular, tricyclic aryl or heteroaryl piperazine diamide derivatives that possess unique antiviral activity are set forth. These compounds are useful for the treatment of HIV and AIDS. The compounds herein have the general Formula I: wherein: Y is selected from the group of indole or azaindole systems: and Z is selected from the group of:

  本文描述了具有药物和生物影响特性的化合物，包括它们的特性、制药组合物和使用方法。特别地，本文阐述了具有独特抗病毒活性的三环芳基或杂芳基哌嗪二酰胺衍生物。这些化合物可用于治疗艾滋病毒和艾滋病。本文中的化合物具有通用的I式：其中：Y选自吲哚或氮杂吲哚系统的群体；Z选自：
• Indole, azaindole and related heterocyclic 4-alkenyl piperidine amides
  申请人：Bristol-Myers Squibb Company

  公开号：EP1513832B1

  公开（公告）日：2014-03-05
• US8450361B2
  申请人：——

  公开号：US8450361B2

  公开（公告）日：2013-05-28