(5R,8R,10R)-1,6-dimethyl-8-ergolinecarboxylic acid | 35470-52-1

• 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: (5R,8R,10R)-1,6-dimethyl-8-ergolinecarboxylic acid
• 英文别名: 1-methyldihydrolysergic acid；1,6-dimethyl-ergoline-8-carboxylic acid；1,6-dimethyl-ergoline-8β-carboxylic acid；1,6-dimethylergoline-8β-carboxylic acid；1,6-dimethyl-8β-carboxy-ergoline；1-Methyl-D-dihydrolyserg(I)-saeure；(6aR,9R,10aR)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-carboxylic acid
• CAS: 35470-52-1
• 化学式: C₁₇H₂₀N₂O₂
• 分子量: 284.358
• InChiKey: GKNGHJGPLVPARI-UXIGCNINSA-N

物化性质

• 沸点：
  514.0±50.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (5R,8R,10R)-1,6-dimethyl-8-ergolinecarboxylic acid 在 potassium carbonate 、 氯甲酸异丁酯 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (6aR,9R,10aR)-4,7-Dimethyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinoline-9-carboxylic acid cyclohexylamide
  参考文献：
  名称：

  (8.beta.)-6-Methylergoline amide derivatives as serotonin antagonists: N1-substituent effects on vascular 5HT2 receptor activity

  摘要：

  A series of (8 beta)-6-methylergoline amide derivatives was synthesized with various alkyl substituents in the N1-position in order to evaluate their effectiveness in blocking vascular 5HT2 receptors. The influence of both the N1 substituent and amide derivative proved to be of great importance on binding affinities to vascular 5HT2 receptors. Within each series of amides, however, maximum affinity was achieved with an N1-isopropyl substituent (14, 18, 26, 38, and 41; all with 2.7-50 times greater affinity than their N1-H analogues), with the exception of two cases (22 and 37) in the cyclohexylamide derivatives wherein N1-methyl equalled the isopropyl in potency. Other than these exceptions, affinities followed the pattern of H less than Me less than Et less than iPr, with potencies falling off with larger alkyl substituents.

  DOI：

  10.1021/jm00164a029
• 作为产物：
  描述：

  (6aR,9R,10aR)-N-(1-hydroxypropan-2-yl)-4,7-dimethyl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-carboxamide 生成 (5R,8R,10R)-1,6-dimethyl-8-ergolinecarboxylic acid
  参考文献：
  名称：

  MAGONE, KARACSONY, E.;BALOGH, T.;LANG, T.;USKERT, A.;DANCSI, L.;LORINCZ, +

  摘要：

  DOI：

文献信息

• Alkylation of ergoline derivatives at position N(1)
  作者：Jan Šmidrkal、Miroslav Semonský

  DOI：10.1135/cccc19820622

  日期：——

  N₍₁₎-Alkyl-8β-ergolines I-XII were prepared by alkylation of 8β-ergoline derivatives XIII to XVIII with alkyl halides in dimethyl sulphoxide in the presence of potassium hydroxide. The compounds I-XII exhibited weak inhibition effects on the secretion of prolactin

  N₍₁₎-烷基-8β-麦角酸衍生物 I-XII 通过在二甲基亚砜中存在氢氧化钾的情况下，用烷基卤化物烷基化8β-麦角酸衍生物 XIII 至 XVIII 制备而成。化合物 I-XII 对催乳素分泌表现出弱的抑制作用
• N-substituted ergoline- and
  申请人：Sandoz Ltd.

  公开号：US04783464A1

  公开（公告）日：1988-11-08

  Novel N-substituted ergoline- and 9,10-didehydro-8-carboxamide- and -8-aminomethyl-derivatives for the treatment of vascular headaches, especially migraine, and of orthostatic hypotension.

  用于治疗血管性头痛，特别是偏头痛和直立性低血压的新型N-取代的埃尔哥林和9,10-二去氢-8-羧酰胺和8-氨基甲基衍生物。
• Ergoline carboxamides
  申请人：Farmitalia Carlo Erba S.p.A.

  公开号：US04632990A1

  公开（公告）日：1986-12-30

  There are provided ergoline derivatives of the formula: ##STR1## wherein R.sub.1 represents a hydrogen atom or a methyl group, R.sub.2 represents a hydrogen or halogen atom or a methyl group, R.sub.3 represents a hydrogen atom or a methoxy group, R.sub.4 represents a hydrocarbon group having from 1 to 4 carbon atoms; each of X and W independently represents a hydrogen atom, a methyl group, a chlorine atom or a methoxy group, and n is 0, 1 or 2. A method for their preparation is also provided. The compounds have strong antiprolactin activity.

  提供了公式为：##STR1##的麦角碱衍生物，其中R.sub.1代表氢原子或甲基基团，R.sub.2代表氢原子、卤素原子或甲基基团，R.sub.3代表氢原子或甲氧基，R.sub.4代表碳原子数为1至4个的碳氢基团；X和W各自独立地表示氢原子、甲基基团、氯原子或甲氧基，n为0、1或2。还提供了它们的制备方法。这些化合物具有强的抗泌乳素活性。
• Dimethylaminoalkyl-3-(ergoline-8'.beta.carbonyl)-ureas
  申请人：Farmitalia Carlo Erba, S.p.A.

  公开号：US04526892A1

  公开（公告）日：1985-07-02

  Novel ergoline derivatives formed by reaction of an 8-carboxy ergoline with a carbodiimide and having hypotensive and antiprolatinic activity.

  通过8-羧基艾角霉素与卡博二腙反应形成的新型艾角霉素衍生物，具有降压和抗催乳作用。
• Ergoline derivatives, process for producing the ergoline derivatives and pharmaceutical compositions containing them
  申请人：FARMITALIA CARLO ERBA S.p.A.

  公开号：EP0091652A1

  公开（公告）日：1983-10-19

  There are provided ergoline derivatives of the formula (I) wherein R, represents a hydrogen atom or a methyl group, R2 represents a hydrogen or halogen atom or a methyl group, R3 represents a hydrogen atom or a methoxy group, R4 represents a hydrocarbon group having from 1 to 4 carbon atoms; each of X and W independently represents a hydrogen atom, a methyl group, a chlorine atom or a methoxy group, and n is 0, 1 or 2. A method for their preparation is also provided. The compounds have strong anti-prolactin activity.

  提供了式(I)的麦角啉衍生物 其中 R 代表氢原子或甲基，R2 代表氢原子、卤素原子或甲基，R3 代表氢原子或甲氧基，R4 代表具有 1 至 4 个碳原子的烃基；X 和 W 各自独立地代表氢原子、甲基、氯原子或甲氧基，n 为 0、1 或 2。 此外，还提供了一种制备方法。这些化合物具有很强的抗泌乳素活性。