(3β,5β,8β)-9,10-didehydro-2,3-dihydro-6-methyl-8-(methylthiomethyl)ergoline | 114249-78-4

• 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-6-methyl-8-(methylthiomethyl)ergoline
• 英文别名: (3β,5β,8β)-9,10-didehydro-2,3-dihydro-6-methyl-8-[(methylthio)methyl]ergoline；(3beta,5beta,8beta)-9,10-didehydro-2,3-dihydro-6-methyl-8-(methylthiomethyl)ergoline；(3beta,5beta,8beta)-9,10-Didehydro-2,3-dihydro-6-methyl-8-(methylthiomethyl) ergoline；(5aS,6aR,9R)-7-methyl-9-(methylsulfanylmethyl)-5,5a,6,6a,8,9-hexahydro-4H-indolo[4,3-fg]quinoline
• CAS: 114249-78-4
• 化学式: C₁₇H₂₂N₂S
• 分子量: 286.441
• InChiKey: OZIWRHKRMMZRKP-XHBSWPGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  40.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (6aR,9R)-7-Methyl-9-methylsulfanylmethyl-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 5.0h， 以42%的产率得到(3β,5β,8β)-9,10-didehydro-2,3-dihydro-6-methyl-8-(methylthiomethyl)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

• 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：——