spiro[cyclopentane-1,9'-(3,7-diaza-bicyclo[3.3.1]nonane)]-2',4',6',8'-tetraone | 90961-77-6

• 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
• 英文名称: spiro[cyclopentane-1,9'-(3,7-diaza-bicyclo[3.3.1]nonane)]-2',4',6',8'-tetraone
• 英文别名: Spiro[cyclopentan-1,9'-(3,7-diaza-bicyclo[3.3.1]nonan)]-2',4',6',8'-tetraon；3,7-Diazaspiro[bicyclo[3.3.1]nonane-9,1'-cyclopentane]-2,4,6,8-tetraone；spiro[3,7-diazabicyclo[3.3.1]nonane-9,1'-cyclopentane]-2,4,6,8-tetrone
• CAS: 90961-77-6
• 化学式: C₁₁H₁₂N₂O₄
• 分子量: 236.227
• InChiKey: DEBNHVDEFPYJRS-UHFFFAOYSA-N

物化性质

• 沸点：
  579.8±50.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  92.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  spiro[cyclopentane-1,9'-(3,7-diaza-bicyclo[3.3.1]nonane)]-2',4',6',8'-tetraone 在 lithium aluminium tetrahydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 生成 替地沙米
  参考文献：
  名称：

  Synthesis, Pharmacological Characterization, and Quantitative Structure−Activity Relationship Analyses of 3,7,9,9-Tetraalkylbispidines:  Derivatives with Specific Bradycardic Activity

  摘要：

  A series of 3,7,9,9-tetraalkyl-3,7-diazabicyclo[3.3.1]nonane derivatives (bispidines) was synthesized and identified as potential antiischemic agents. Pharmacological experiments in vitro as well as in vivo are described, and the results are listed. For selection of those compounds fitting best to the desired profile of a specific bradycardic antianginal agent-decrease in heart rate without affecting contractility and blood pressure-these results were scored and ranked. Quantitative structure-activity relationship (QSAR) analyses were performed and discussed a posteriori by means of Hansch, nonelementary discriminant and factor analysis to get insight into the molecular features determining the biological profile. Highly significant equations were obtained, indicating hydrophobic and steric effects. Both pharmacological ranking and QSAR considerations showed compound 6 as the optimum within the structural class under investigation. Compound 6 (tedisamil, KC8857) has been selected as the most promising compound and was chosen for further pharmacological and clinical investigations as an antiischemic drug.

  DOI：

  10.1021/jm970120q
• 作为产物：
  描述：

  4',8'-diamino-spiro[cyclopentane-1,9'-(3,7-diaza-bicyclo[3.3.1]nona-3,7-diene)]-2',6'-dione 在 盐酸 作用下， 生成 spiro[cyclopentane-1,9'-(3,7-diaza-bicyclo[3.3.1]nonane)]-2',4',6',8'-tetraone
  参考文献：
  名称：

  Kon; Thorpe, Journal of the Chemical Society, 1919, vol. 115, p. 702

  摘要：

  DOI：

文献信息

• Synthesis of New Tricyclic Spirobispidines via Ring Closing Metathesis Reaction
  作者：Christian Hametner、Daniel Dangl、Kurt Mereiter、Martina Marchetti、Johannes Fröhlich

  DOI：10.3987/com-07-11063

  日期：——

  New tricyclic spiro compounds based on 3,7-diazabicyclo[3.3.1]-nonane (bispidine) were synthesized by ruthenium-catalyzed ring closing metathesis reactions. The constitution of the newly formed double bond depending on the chain length and various conditions of the RCM reaction was analyzed.
• SCHOEN, U.;HACHMEISTER, B.;KEHRBACH, W.;KUEHL, U.;BUSCHMANN, G.
  作者：SCHOEN, U.、HACHMEISTER, B.、KEHRBACH, W.、KUEHL, U.、BUSCHMANN, G.

  DOI：——

  日期：——
• Synthesis, Pharmacological Characterization, and Quantitative Structure−Activity Relationship Analyses of 3,7,9,9-Tetraalkylbispidines:  Derivatives with Specific Bradycardic Activity
  作者：Uwe Schön、Jochen Antel、Reinhard Brückner、Josef Messinger、Rainer Franke、Andreas Gruska

  DOI：10.1021/jm970120q

  日期：1998.1.1

  A series of 3,7,9,9-tetraalkyl-3,7-diazabicyclo[3.3.1]nonane derivatives (bispidines) was synthesized and identified as potential antiischemic agents. Pharmacological experiments in vitro as well as in vivo are described, and the results are listed. For selection of those compounds fitting best to the desired profile of a specific bradycardic antianginal agent-decrease in heart rate without affecting contractility and blood pressure-these results were scored and ranked. Quantitative structure-activity relationship (QSAR) analyses were performed and discussed a posteriori by means of Hansch, nonelementary discriminant and factor analysis to get insight into the molecular features determining the biological profile. Highly significant equations were obtained, indicating hydrophobic and steric effects. Both pharmacological ranking and QSAR considerations showed compound 6 as the optimum within the structural class under investigation. Compound 6 (tedisamil, KC8857) has been selected as the most promising compound and was chosen for further pharmacological and clinical investigations as an antiischemic drug.
• Kon; Thorpe, Journal of the Chemical Society, 1919, vol. 115, p. 702
  作者：Kon、Thorpe

  DOI：——

  日期：——