6-Methyl-5βH-9-ergolen-8β-acetonitril | 19649-11-7

• 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: 6-Methyl-5βH-9-ergolen-8β-acetonitril
• 英文别名: (6-methyl-9,10-didehydro-ergolin-8-yl)-acetonitrile；(5β,8β)-9,10-didehydro-6-methylergoline-8-acetonitrile；(5beta,8beta)-9,10-Didehydro-6-methylergoline-8-acetonitrile；2-[(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinolin-9-yl]acetonitrile
• CAS: 19649-11-7
• 化学式: C₁₇H₁₇N₃
• 分子量: 263.342
• InChiKey: GPXUFFCMCLXKSW-BDJLRTHQSA-N

物化性质

• 熔点：
  232-235 °C
• 沸点：
  519.4±45.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  42.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-Methyl-5βH-9-ergolen-8β-acetonitril 在 三乙基硅烷 、 三氟乙酸 作用下， 以37%的产率得到(3β,5β,8β)-9,10-didehydro-2,3-dihydro-6-methylergoline-8-acetonitrile
  参考文献：
  名称：

  Optionally substituted (3.beta.-9,10-didehydro-2,3-dihydro ergoline as

  摘要：

  本发明揭示了一种采用2,3-二氢麦角酸衍生物的治疗方法。该方法增强了哺乳动物神经系统中的5-羟色胺功能，因此可以应用于包括记忆、抑郁症、焦虑症、疼痛和食欲等5-羟色胺介导的生理表现。还揭示了含有所述2,3-二氢麦角酸衍生物的药物组合物，与药用惯用稀释剂和载体混合。

  公开号：

  US04798834A1

文献信息

• Ergolines as selective 5-HT1 agonists
  作者：John S. Ward、Ray W. Fuller、Leander Merritt、Harold D. Snoddy、Jonathan W. Paschal、Norman R. Mason、J. S. Horng

  DOI：10.1021/jm00403a007

  日期：1988.8

  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.
• 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