2-(3-哌啶-1-基丙基)-8,8-二丙基-2-氮杂螺[4.5]癸烷 | 123018-48-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氮杂螺癸烷衍生物
• 中文名称: 2-(3-哌啶-1-基丙基)-8,8-二丙基-2-氮杂螺[4.5]癸烷
• 英文名称: SKandF 106610
• 英文别名: 2-(3-piperidinopropyl)-8,8-dipropyl-2-azaspiro [4.5]decane；2-(3-piperidinopropyl)-8,8-dipropyl-2-azaspiro[4.5]decane；2-(3-(1-Piperidinyl)propyl)-8,8-dipropyl-2-azaspiro(4.5)decane；2-(3-piperidin-1-ylpropyl)-8,8-dipropyl-2-azaspiro[4.5]decane
• CAS: 123018-48-4
• 化学式: C₂₃H₄₄N₂
• 分子量: 348.616
• InChiKey: FPYDSYNEQOHKET-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  25
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(3-piperidin-1-ylpropyl)-8,8-dipropyl-2-azaspiro[4.5]decane-1,3-dione 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 3.0h， 生成 2-(3-哌啶-1-基丙基)-8,8-二丙基-2-氮杂螺[4.5]癸烷
  参考文献：
  名称：

  Antiarthritic and supressor cell inducing activity of azaspiranes: structure-function relationships of a novel class of immunomodulatory agents

  摘要：

  Spirogermanium (1; 8,8-diethyl-N,N-dimethyl-2-aza-8- germaspiro[4.5]decane-2-propanamine dihydrochloride) is a potent cytotoxic agent in vitro which has demonstrated limited activity in experimental animal tumor models. Subsequently, it has been reported that spirogermanium has antiarthritic and suppressor cell-inducing activity. We have synthesized a series of substituted 8-hetero-2-azaspiro[4.5]decane and 9-hetero-3-azaspiro[5.5]undecane analogues of spirogermanium to identify the heteroatom requirements for in vivo antiarthritic and suppressor cell-inducing activity. This structure-activity relationship study has identified that appropriately substituted silicon and carbon analogues of spirogermanium retain both antiarthritic and immunosuppressive activity, with the 8,8-dipropyl (carbon) analogue being among the most active. Following the identification of N,N-dimethyl-8,8-dipropyl-2-azaspiro[4.5]decane-2-propanamine++ + dihydrochloride (9) as a more active analogue than spirogermanium, a series of 8,8-dipropyl analogues with various amine substituents were synthesized. A number of these analogues had activity similar to that of 9. A correlation between activity in the adjuvant arthritic rat and the ability to induce suppressor cells (r = 0.894, p less than 0.001) suggests an association between the two pharmacologic effects. While the precise biochemical mechanism(s) for the pharmacological activity is unclear, these data suggest that compounds within this series, e.g., N,N-dimethyl-8,8-dipropyl-2-azaspiro[4.5]decane-2-propanamine++ + dihydrochloride, may provide effective therapy in diseases of autoimmune origin and/or the prevention of rejection in tissue transplantation.

  DOI：

  10.1021/jm00173a010

文献信息

• Small molecule immunopotentiators and assays for their detection
  申请人：Novartis Vaccines and Diagnostics, Inc.

  公开号：EP2583678A2

  公开（公告）日：2013-04-24

  The invention provides immunostimulatory compositions comprising a small molecule immuno-potentiator (SMIP) compound and methods of administration thereof. Also provided are methods of administering a SMIP compound in an effective amount to enhance the immune response of a subject to an antigen. Further provided are novel compositions and methods of administering SMIP compounds alone or in combination with another agent for the treatment of cancer, infectious diseases and/or allergies/asthma. In a further aspect, the invention relates generally to methods of screening for small molecule immuno-modulatory compositions.

  本发明提供了包含小分子免疫促进剂（SMIP）化合物的免疫刺激组合物及其施用方法。还提供了施用有效量的 SMIP 化合物以增强受试者对抗原的免疫应答的方法。本发明还提供了单独施用 SMIP 化合物或与另一种制剂联合施用 SMIP 化合物以治疗癌症、传染性疾病和/或过敏/哮喘的新型组合物和方法。在另一方面，本发明一般涉及筛选小分子免疫调节组合物的方法。
• METHODS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0550595A1

  公开（公告）日：1993-07-14
• EP0550595A4
  申请人：——

  公开号：EP0550595A4

  公开（公告）日：1993-09-08
• PROCESS FOR PREPARING SPIROCYCLIC LACTAMS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0733042A1

  公开（公告）日：1996-09-25
• EP0733042A4
  申请人：——

  公开号：EP0733042A4

  公开（公告）日：1996-07-30