(2R,11bR)-9,10-dimethoxyspiro[1,3,4,6,7,11b-hexahydrobenzo[a]quinolizine-2,2'-oxirane] | 83917-83-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: (2R,11bR)-9,10-dimethoxyspiro[1,3,4,6,7,11b-hexahydrobenzo[a]quinolizine-2,2'-oxirane]
• CAS: 83917-83-3
• 化学式: C₁₆H₂₁NO₃
• 分子量: 275.348
• InChiKey: GYKMHOQTBMONGT-CZUORRHYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.17
• 重原子数：
  20.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  34.23
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (2R,11bR)-9,10-dimethoxyspiro[1,3,4,6,7,11b-hexahydrobenzo[a]quinolizine-2,2'-oxirane] 、 甲胺 生成 (2S,11bS)-9,10-Dimethoxy-2-methylaminomethyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-ol
  参考文献：
  名称：

  Antihypertensive 9-substituted 1-0xa-4,9-diazaspiro[5.5]undecan-3-ones

  摘要：

  Forty-one 9-substituted 1-oxa-4,9-diazaspiro[5.5]undecan-3-ones were prepared for antihypertensive screening in the spontaneously hypertensive rat (SHR). For the 9-(2-indol-3-ylethyl) series, the parent compound, 9-(2-indol-3-ylethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-3-one (21), was the most potent antihypertensive agent. Substitution of lower alkyl groups on the spirolactam ring gave compounds close in activity to 21, while substitution with large alkyl or aryl groups led to a significant decrease in activity. Ring-opened analogues of 21 that contained the same functionality were markedly less active. Several 1-oxa-4,9-diazaspiro[5.5]undecan-3-ones substituted at the 9 position with 1,4-benzodioxan-2-ylmethyl, 1,4-benzodioxan-2-ylhydroxyethyl, and 2-phenylethyl groups also demonstrated significant activity. Compound 21 was chosen for a detailed pharmacological evaluation. Its antihypertensive activity appears to be predominantly due to peripheral alpha 1-adrenoceptor blockade.

  DOI：

  10.1021/jm00360a013
• 作为产物：
  描述：

  6,7-二甲氧基-3,4-二氢异喹啉盐酸盐 反应 1.5h， 生成 (2R,11bR)-9,10-dimethoxyspiro[1,3,4,6,7,11b-hexahydrobenzo[a]quinolizine-2,2'-oxirane]
  参考文献：
  名称：

  Synthesis and antihypertensive activity of a series of spiro[1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizine-2,5'-oxazolidin-2'-one]s

  摘要：

  The 2R*,11bS* and 2S*,11bS* diastereoisomers of the spiro[1,3,4,6,7,11b-hexahydro-2H-benzo[a]quinolizine-2, 5'-oxazolidin-2'-one] system were prepared by stereoselective methods. Evaluation of these compounds for antihypertensive activity by oral administration to the spontaneously hypertensive rat showed the 2S*,11bS* series was the more potent. Within that series it was found that small alkyl substituents at positions 3 and 4' enhanced antihypertensive activity and that methoxyl substitution at positions 9 and 10 was optimal. (2S,3S,11bS)-Spiro-[2-ethyl-9,10-dimethoxy-1,3,4,6,7, 11b-hexahydro-2H-benzo[a]quinolizine-2,5'-oxazolidin-2'-one] [(-)-9e] was one of the most efficacious compounds of this series, while its antipode, (+)-9e, was inactive. Selected compounds in this series were shown to be alpha-adrenoceptor antagonists.

  DOI：

  10.1021/jm00364a013

文献信息

• DAVIS, R.;KLUGE, A. F.;MADDOX, M. L.;SPARACINO, M. L., J. ORG. CHEM., 1983, 48, N 2, 255-259
  作者：DAVIS, R.、KLUGE, A. F.、MADDOX, M. L.、SPARACINO, M. L.

  DOI：——

  日期：——