1-ethyldihydrolysergic acid | 41710-25-2

• 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: 1-ethyldihydrolysergic acid
• 英文别名: (6aR,9R,10aR)-4-ethyl-7-methyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-carboxylic acid
• CAS: 41710-25-2
• 化学式: C₁₈H₂₂N₂O₂
• 分子量: 298.385
• InChiKey: QPSBGDFCKNDDLA-XNRPHZJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  45.47
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-ethyldihydrolysergic acid 、 环戊胺 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 5.0h， 以14.5%的产率得到(8β)-N-cyclopentyl-1-ethyl-6-methylergoline-8-carboxamide
  参考文献：
  名称：

  (8.beta.)-6-Methylergoline amide derivatives as serotonin antagonists: N1-substituent effects on vascular 5HT2 receptor activity

  摘要：

  A series of (8 beta)-6-methylergoline amide derivatives was synthesized with various alkyl substituents in the N1-position in order to evaluate their effectiveness in blocking vascular 5HT2 receptors. The influence of both the N1 substituent and amide derivative proved to be of great importance on binding affinities to vascular 5HT2 receptors. Within each series of amides, however, maximum affinity was achieved with an N1-isopropyl substituent (14, 18, 26, 38, and 41; all with 2.7-50 times greater affinity than their N1-H analogues), with the exception of two cases (22 and 37) in the cyclohexylamide derivatives wherein N1-methyl equalled the isopropyl in potency. Other than these exceptions, affinities followed the pattern of H less than Me less than Et less than iPr, with potencies falling off with larger alkyl substituents.

  DOI：

  10.1021/jm00164a029
• 作为产物：
  描述：

  碘乙烷 、 9,10-二氢麦角酸 在 氢氧化钾 作用下， 以 二甲基亚砜 为溶剂， 以47%的产率得到1-ethyldihydrolysergic acid
  参考文献：
  名称：

  Alkylation of ergoline derivatives at position N(1)

  摘要：

  N₍₁₎-烷基-8β-麦角酸衍生物 I-XII 通过在二甲基亚砜中存在氢氧化钾的情况下，用烷基卤化物烷基化8β-麦角酸衍生物 XIII 至 XVIII 制备而成。化合物 I-XII 对催乳素分泌表现出弱的抑制作用

  DOI：

  10.1135/cccc19820622

文献信息

• 6-Methylergoline-8-carboxylic acid esters as serotonin antagonists: N1-substituent effects on 5HT2 receptor affinity
  作者：Gifford Marzoni、William L. Garbrecht、Pawel Fludzinski、Marlene L. Cohen

  DOI：10.1021/jm00393a024

  日期：1987.10

  Three series of 6-methylergoline-8-carboxylic acid esters with various alkyl substituents in the N1-position were prepared and their 5HT2 receptor affinities measured. Some overlap occurred in the 5HT2 receptor affinities of the different ester series, indicating that both the ester side chain and the indole substituent influenced 5HT2 receptor affinity. While 5HT2 receptor affinity was affected by the structure of the ester side chain, the N1-substituent played a more crucial role in determining 5HT2 receptor affinity. When the ester side chain was held constant, maximal 5HT2 receptor affinity for that series of esters was obtained when the N1-substituent was isopropyl. Smaller substituents in the N1-position resulted in reduced 5HT2 receptor affinity. Groups C4 or larger in the N1-position resulted in a further decline in 5HT2 receptor affinity. The importance of the N1-substituent in determining 5HT2 receptor affinity was further substantiated when several 2-methyl-3-ethyl-5-(dimethylamino)indoles with various N1-substituents were tested. Again, maximal 5HT2 receptor affinity was obtained when the N1-substituent was isopropyl.