9-ethyl-9-methyl-3,7-diaza-bicyclo[3.3.1]nonane-2,4,6,8-tetraone | 90961-79-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 9-ethyl-9-methyl-3,7-diaza-bicyclo[3.3.1]nonane-2,4,6,8-tetraone
• 英文别名: 9-Aethyl-9-methyl-3,7-diaza-bicyclo[3.3.1]nonan-2,4,6,8-tetraon；9-Ethyl-9-methyl-3,7-diazabicyclo[3.3.1]nonane-2,4,6,8-tetrone
• CAS: 90961-79-8
• 化学式: C₁₀H₁₂N₂O₄
• 分子量: 224.216
• InChiKey: WRAXMCOZUDZMRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 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：

  9-ethyl-9-methyl-3,7-diaza-bicyclo[3.3.1]nonane-2,4,6,8-tetraone 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 4.0h， 生成 3,7-Bis(cyclohexylmethyl)-9-ethyl-9-methyl-3,7-diazabicyclo[3.3.1]nonane
  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：

  2,4-二氰基-3-乙基-3-甲基戊二酰亚胺 在 磷酸 、 硫酸 作用下， 以84%的产率得到9-ethyl-9-methyl-3,7-diaza-bicyclo[3.3.1]nonane-2,4,6,8-tetraone
  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

文献信息

• Thole; Thorpe, Journal of the Chemical Society, 1911, vol. 99, p. 440
  作者：Thole、Thorpe

  DOI：——

  日期：——
• Thorpe; Wood, Journal of the Chemical Society, 1913, vol. 103, p. 1575
  作者：Thorpe、Wood

  DOI：——

  日期：——
• Handley,G.J. et al., Australian Journal of Chemistry, 1960, vol. 13, p. 129 - 144
  作者：Handley,G.J. et al.

  DOI：——

  日期：——
• 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.