(6aR,9R)-7-Methyl-9-phenylsulfanylmethyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline | 114298-11-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (6aR,9R)-7-Methyl-9-phenylsulfanylmethyl-4,6,6a,7,8,9-hexahydro-indolo[4,3-fg]quinoline
• 英文别名: (5beta,8beta)-9,10-Didehydro-6-methyl-8-(phenylthiomethyl)ergoline；(6aR,9R)-7-methyl-9-(phenylsulfanylmethyl)-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline
• CAS: 114298-11-2
• 化学式: C₂₂H₂₂N₂S
• 分子量: 346.496
• InChiKey: VUCJDZKAAFYUSE-QVKFZJNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  44.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (6aR,9R)-7-Methyl-9-phenylsulfanylmethyl-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， 以35%的产率得到(3β,5β,8β)-9,10-didehydro-2,3-dihydro-6-methyl-8-(phenylthiomethyl)ergoline
  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

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

  公开号：EP0306191A2

  公开（公告）日：1989-03-08

  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 serotonin­mediated 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.

  本研究公开了一种使用 2,3-二氢麦角酚碱的治疗方法。该方法可增强有需要的哺乳动物神经系统中的血清素能功能，从而应用于血清素介导的生理表现，包括记忆、抑郁、焦虑、疼痛和食欲。此外，还公开了含有所述 2,3-二氢麦角林的药物组合物，该组合物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：——
• US4798834A
  申请人：——

  公开号：US4798834A

  公开（公告）日：1989-01-17