(3β,5β,8β)-9,10-didehydro-2,3-dihydro-8-methyl-6-propylergoline | 114249-83-1

• 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: (3β,5β,8β)-9,10-didehydro-2,3-dihydro-8-methyl-6-propylergoline
• 英文别名: (3beta,5beta,8beta)-9,10-Didehydro-2,3-dihydro-8-methyl-6-propylergoline；(5aS,6aR,9R)-9-methyl-7-propyl-5,5a,6,6a,8,9-hexahydro-4H-indolo[4,3-fg]quinoline
• CAS: 114249-83-1
• 化学式: C₁₈H₂₄N₂
• 分子量: 268.402
• InChiKey: PCXDSVMGNSSSQR-PBFPGSCMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  15.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (6aR,9R)-9-Methyl-7-propyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline 在 三乙基硅烷 、 三氟乙酸 作用下， 反应 6.0h， 以7%的产率得到(3β,5β,8β)-9,10-didehydro-2,3-dihydro-8-methyl-6-propylergoline
  参考文献：
  名称：

  Ergolines as selective 5-HT1 agonists

  摘要：

  The synthesis and serotonin receptor subtype affinity of a series of ergolines are described. High selectivity for the 5-HT1 subtype was found with a number of 8-substituted (3 beta, 5 beta)-9,10-didehydro-6-methylergolines. The more potent and selective of these compounds increased the concentration of serotonin and decreased the concentration of 5-HIAA in rat brain and increased corticosterone concentration in rat serum. Oral administration of 13, (3 beta)-2,3-dihydrolysergine, produced long-lasting decreases in serotonin turnover. Compound 13 lacked substantial dopaminergic activity as measured by its effects on dopamine turnover in whole brain or striatum and its affinity for alpha-adrenergic binding sites was significantly less than for 5-HT1 binding sites. The increases in serum corticosterone concentrations produced by 13 were not blocked by the serotonin uptake inhibitor fluoxetine or by the serotonin synthesis inhibitor p-chlorophenylalanine, suggesting that 13 exerts its effects through direct stimulation of serotonin receptors.

  DOI：

  10.1021/jm00403a007

文献信息

• Optionally substituted (3.beta.-9,10-didehydro-2,3-dihydro ergoline as
  申请人：Eli Lilly and Company

  公开号：US04798834A1

  公开（公告）日：1989-01-17

  A therapeutic method employing 2,3-dihydroergolines is disclosed. Said method enhances serotonergic function in the nervous system of a mammal in need thereof, thereby finding application in serotonin-mediated physiological manifestations including memory, depression, anxiety, pain and appetite. Also disclosed are pharmaceutical compositions containing said 2,3-dihydroergolines in admixture with pharmaceutically acceptable diluents and carriers.

  本发明揭示了一种利用2,3-二氢埃高啡烷的治疗方法。该方法增强了哺乳动物神经系统中的5-羟色胺功能，从而在包括记忆、抑郁症、焦虑症、疼痛和食欲等5-羟色胺介导的生理表现中找到应用。还揭示了含有所述2,3-二氢埃高啡烷的药物组合物，其与药学上可接受的稀释剂和载体混合。
• WARD, JOHN S.;FULLER, RAY W.;MERRITT, LEANDER;SNODDY, HAROLD D.;PASCHAL, +, J. MED. CHEM., 31,(1988) N 8, C. 1512-1519
  作者：WARD, JOHN S.、FULLER, RAY W.、MERRITT, LEANDER、SNODDY, HAROLD D.、PASCHAL, +

  DOI：——

  日期：——
• 2,3-Dihydroergolines for serotonergic function enhancement
  申请人：ELI LILLY AND COMPANY

  公开号：EP0306191B1

  公开（公告）日：1994-09-14
• US4798834A
  申请人：——

  公开号：US4798834A

  公开（公告）日：1989-01-17