-6-methyl-1-(1-methylethyl)ergoline-8-carboxylic acid 4-methoxycyclohexyl ester

• 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-1-(1-methylethyl)ergoline-8-carboxylic acid 4-methoxycyclohexyl ester
• 英文别名: 4-Methoxycyclohexyl 6-methyl-1-(propan-2-yl)ergoline-8-carboxylate；(4-methoxycyclohexyl) 7-methyl-4-propan-2-yl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-carboxylate
• 化学式: C₂₆H₃₆N₂O₃
• 分子量: 424.583
• InChiKey: RJBJIKXTJIZONR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  43.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(4-methoxycyclohexyl)-4-methylbenzenesulfonate 、 (8β)-6-methyl-1-(1-methylethyl)ergoline-8-carboxylic acid 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 以12.4 g的产率得到-6-methyl-1-(1-methylethyl)ergoline-8-carboxylic acid 4-methoxycyclohexyl ester
  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

• (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.