6-methyl-ergoline-8-carboxylic acid | 2481-70-1

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 麦角林及其衍生物
• 英文名称: 6-methyl-ergoline-8-carboxylic acid
• 英文别名: Dihydrolysergsaeure；(9R)-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxylic acid
• CAS: 2481-70-1；5878-43-3；6838-23-9；6871-64-3
• 化学式: C₁₆H₁₈N₂O₂
• 分子量: 270.331
• InChiKey: ORBSYPFBZQJNJE-PWQPVHBWSA-N

物化性质

• 熔点：
  314-316 °C
• 沸点：
  517.3±50.0 °C(Predicted)
• 密度：
  1.310±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  56.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-methyl-ergoline-8-carboxylic acid 、 环己醇 在 对甲苯磺酸 作用下， 生成 cyclohexyl (9R)-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxylate
  参考文献：
  名称：

  (8.beta.)-Ergoline-8-carboxylic acid cycloalkyl esters as serotonin antagonists: structure-activity study

  摘要：

  A series of (8 beta)-6-methyl-1-(1-methylethyl)ergoline-8-carboxylic acid cycloalkyl esters were prepared and examined for blockade of vascular 5HT2 receptors. The antagonist in this series that had the highest 5HT2 receptor affinity was (8 beta)-6-methyl-1-(1-methylethyl)ergoline-8-carboxylic acid cyclohexyl ester. This compound was therefore chosen as the basic backbone of a structure-activity study to determine what effect different N1-substituents, N6-substituents, and ester ring substituents had on 5HT2 receptor affinity. Maximal 5HT2 receptor affinity was obtained when the N1-substituent was isopropyl, the N6-substituent was methyl, and there was a hydroxy or keto substituent in the 4-position of the ester cyclohexyl ring.

  DOI：

  10.1021/jm00397a030

文献信息

• GARBRECHT, WILLIAM L.;MARZONI, GIFFORD;WHITTEN, KATHLEEN R.;COHEN, MARLEN+, J. MED. CHEM., 31,(1988) N 2, 444-448
  作者：GARBRECHT, WILLIAM L.、MARZONI, GIFFORD、WHITTEN, KATHLEEN R.、COHEN, MARLEN+

  DOI：——

  日期：——
• (8.beta.)-Ergoline-8-carboxylic acid cycloalkyl esters as serotonin antagonists: structure-activity study
  作者：William L. Garbrecht、Gifford Marzoni、Kathleen R. Whitten、Marlene L. Cohen

  DOI：10.1021/jm00397a030

  日期：1988.2

  A series of (8 beta)-6-methyl-1-(1-methylethyl)ergoline-8-carboxylic acid cycloalkyl esters were prepared and examined for blockade of vascular 5HT2 receptors. The antagonist in this series that had the highest 5HT2 receptor affinity was (8 beta)-6-methyl-1-(1-methylethyl)ergoline-8-carboxylic acid cyclohexyl ester. This compound was therefore chosen as the basic backbone of a structure-activity study to determine what effect different N1-substituents, N6-substituents, and ester ring substituents had on 5HT2 receptor affinity. Maximal 5HT2 receptor affinity was obtained when the N1-substituent was isopropyl, the N6-substituent was methyl, and there was a hydroxy or keto substituent in the 4-position of the ester cyclohexyl ring.