isolysergine | 478-90-0

• 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: isolysergine
• 英文别名: Isolysergin；(6aR,9S)-7,9-dimethyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinoline
• CAS: 478-90-0
• 化学式: C₁₆H₁₈N₂
• 分子量: 238.332
• InChiKey: YOZGACBWDKFAAD-ZUZCIYMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  19
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  isolysergine 在 三乙基硅烷 、 三氟乙酸 作用下， 反应 16.0h， 以24%的产率得到(3β)-2,3-dihydroisolysergine
  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
• 作为产物：
  描述：

  (3β)-2,3-Dihydroisolysergine 在 吲哚 、 苯亚硒酸酐 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以90%的产率得到isolysergine
  参考文献：
  名称：

  麦角生物碱全合成中的苯硒酸酐脱氢

  摘要：

  将二氢吲哚与苯基硒二酸酐脱氢成吲哚的标准化程序已成功地应用于麦角生物碱总合成的最终步骤。

  DOI：

  10.1016/s0040-4039(00)98987-1

文献信息

• Dehydrogenation with phenylseleninic anhydride in the total synthesis of ergot alkaloids
  作者：Ichiya Ninomiya、Chiyomi Hashimoto、Toshiko Kiguchi、Derek H.R. Barton、Xavier Lusinchi、Pierre Milliet

  DOI：10.1016/s0040-4039(00)98987-1

  日期：1985.1

  The standardised procedure for dehydrogenation of indolines into indoles with phenylseleninic anhydride was successfully applied to the final steps in the total synthesis of ergot alkaloids.

  将二氢吲哚与苯基硒二酸酐脱氢成吲哚的标准化程序已成功地应用于麦角生物碱总合成的最终步骤。
• Zur Stereochemie der Mutterkornalkaloide vom Agroclavin- und Elymoclavin-Typus. 46. Mitteilung über Mutterkornalkaloide
  作者：E. Schreier

  DOI：10.1002/hlca.19580410708

  日期：——

  Durch die auf verschiedenen, sterisch eindeutigen Wegen durchgeführte chemische Verknüpfung des Mutterkornalkaloids Agroclavin mit Elymoclavin und D-Dihydro-lysergsäure(I) wurde bewiesen, dass die Ringe C und D im Agroclavin gleiche trans-Verknüpfung wie in der D-Dihydro-lysergsäure(I) aufweisen.

  麦角生物碱农作物藤黄与依维藤黄和D-二氢麦角酸的化学键合（I）以不同的，空间明确的方式进行，证明了农藤碱中的环C和D与D中具有相同的反式连接-二氢麦角酸（I）显示出来。
• Kiguchi, Toshiko; Hashimoto, Chiyomi; Ninomiya, Ichiya, Heterocycles, 1985, vol. 23, # 8, p. 1925 - 1928
  作者：Kiguchi, Toshiko、Hashimoto, Chiyomi、Ninomiya, Ichiya

  DOI：——

  日期：——
• Concise total syntheses of lysergene, lysergine, isolysergine and festuclavine
  作者：Nikhil R. Tasker、Peter Wipf

  DOI：10.24820/ark.5550190.p012.120

  日期：——
• 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.