1-异丙基二氢麦角酸 | 41710-27-4

• 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
• 中文名称: 1-异丙基二氢麦角酸
• 中文别名: (6AR,9R,10AR)-4-异丙基-7-甲基-4,6,6A,7,8,9,10,10A-八氢吲哚并[4,3-FG]喹啉-9-羧酸
• 英文名称: 1-isopropyldihydrolysergic acid
• 英文别名: (8β)-6-methyl-1-(1-methylethyl)ergoline-8-carboxylic acid；(8β)-1-isopropyl-6-methylergoline-8-carboxylic acid；(6aR,9R,10aR)-7-methyl-4-propan-2-yl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-carboxylic acid
• CAS: 41710-27-4
• 化学式: C₁₉H₂₄N₂O₂
• 分子量: 312.412
• InChiKey: NAGMITMLYCSORO-FRFSOERESA-N

物化性质

• 沸点：
  515.9±50.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  23
• 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：
  45.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-异丙基二氢麦角酸 生成 [(2R,3R)-3-hydroxybutan-2-yl] (6aR,9R,10aR)-7-methyl-4-propan-2-yl-6,6a,8,9,10,10a-hexahydroindolo[4,3-fg]quinoline-9-carboxylate
  参考文献：
  名称：

  MARZONI, GIFFORD P.;GARBRECHT, WILLIAM L.

  摘要：

  DOI：
• 作为产物：
  描述：

  2-碘代丙烷 、 9,10-二氢麦角酸 在 氨 、 sodium amide 作用下， 生成 1-异丙基二氢麦角酸
  参考文献：
  名称：

  6-Methylergoline-8-carboxylic acid esters as serotonin antagonists: N1-substituent effects on 5HT2 receptor affinity

  摘要：

  Three series of 6-methylergoline-8-carboxylic acid esters with various alkyl substituents in the N1-position were prepared and their 5HT2 receptor affinities measured. Some overlap occurred in the 5HT2 receptor affinities of the different ester series, indicating that both the ester side chain and the indole substituent influenced 5HT2 receptor affinity. While 5HT2 receptor affinity was affected by the structure of the ester side chain, the N1-substituent played a more crucial role in determining 5HT2 receptor affinity. When the ester side chain was held constant, maximal 5HT2 receptor affinity for that series of esters was obtained when the N1-substituent was isopropyl. Smaller substituents in the N1-position resulted in reduced 5HT2 receptor affinity. Groups C4 or larger in the N1-position resulted in a further decline in 5HT2 receptor affinity. The importance of the N1-substituent in determining 5HT2 receptor affinity was further substantiated when several 2-methyl-3-ethyl-5-(dimethylamino)indoles with various N1-substituents were tested. Again, maximal 5HT2 receptor affinity was obtained when the N1-substituent was isopropyl.

  DOI：

  10.1021/jm00393a024

文献信息

• Heteroalkylamides of (8-.beta.)-1-alkyl-6-(substituted)ergolines useful
  申请人：Eli Lilly and Company

  公开号：US04902691A1

  公开（公告）日：1990-02-20

  This invention provides (8.beta.)-N-heteroalkyl-1-alkyl-6-(substituted)ergoline-8-carboxamides useful for blocking 5HT.sub.2 receptors in mammals having an excess of serotonin centrally or peripherally. The invention also provides methods for treating sexual dysfunction, hypertension, migraine, vasospasm, thrombosis, ischemia, depression, anxiety, sleep disorders and appetite disorders with a compound of the invention.

  这项发明提供了对于中枢或外周存在多余5-羟色胺的哺乳动物中有用的(8.β.)-N-杂代烷基-1-烷基-6-(取代)麦角酸酰胺，用于阻断5HT.sub.2受体。该发明还提供了使用该化合物治疗性功能障碍、高血压、偏头痛、血管痉挛、血栓形成、缺血、抑郁症、焦虑症、睡眠障碍和食欲障碍的方法。
• Cycloalkylamides of (8.beta.)-1-alkyl-6-(substituted) ergolines
  申请人：Eli Lilly and Company

  公开号：US04931447A1

  公开（公告）日：1990-06-05

  This invention provides (8.beta.)-N-cycloalkyl-1-alkyl-6-(substituted) ergoline-8-carboxamides useful for blocking 5HT.sub.2 receptors in mammals having an excess of serotonin centrally or peripherally. The invention also provides methods for treating hypertension, migraine, vasospasm, thrombosis, ischemia, depression, anxiety, sleep disorders and appetite disorders with a compound of the invention.

  本发明提供了一种(8.beta.)-N-环烷基-1-烷基-6-(取代基) 艾角酸酰胺，用于阻断中枢或外周存在过量血清素的哺乳动物的5HT.sub.2 受体。本发明还提供了使用本发明化合物治疗高血压、偏头痛、血管痉挛、血栓形成、缺血、抑郁症、焦虑症、睡眠障碍和食欲障碍的方法。
• Substituted cyclo or bicycloalkylamides of (8.beta.)-6-(substituted)
  申请人：Eli Lilly and Company

  公开号：US05441961A1

  公开（公告）日：1995-08-15

  The present invention provides (8.beta.)-N-substituted cyclo or bicycloalkyl-6-(substituted)-ergoline-8-carboxamides useful for occupying 5HT.sub.2 or 5HT.sub.1c receptors in mammals. The invention also provides methods for treating a variety of disorders and conditions related to or affecting these receptors as well as pharmaceutical formulations of the compounds of the invention.

  本发明提供了(8.beta.)-N-取代环或双环烷基-6-(取代)-麦角酸酰胺，用于占据哺乳动物中的5HT.sub.2或5HT.sub.1c受体。本发明还提供了用于治疗与这些受体有关或影响这些受体的多种疾病和病症的方法，以及本发明化合物的制药配方。
• Improvements in or relating to ergoline derivatives
  申请人：ELI LILLY AND COMPANY

  公开号：EP0375297A2

  公开（公告）日：1990-06-27

  (8β)-N-heteroalkyl-1- alkyl-6-(substituted) ergoline-8-carboxamides of the formula wherein: R¹ is C₁-C₄ alkyl; R² is allyl or C₁-C₄ straight chain alkyl; R³ is hydrogen or C₁-C₄ straight chain alkyl; R⁴ is pyridinyl or imidazolyl; alk is a divalent organic radical derived from a straight or branched C₁-C₅ alkane; or a pharmaceutically acceptable acid addition salt thereof. The compounds are useful for blocking 5HT₂ receptors in mammals having an excess of serotonin centrally or peripherally

  (8β)-N-杂烷基-1-烷基-6-（取代的）麦角啉-8-甲酰胺，其式为 其中 R¹ 是 C₁-C₄ 烷基； R² 是烯丙基或 C₁-C₄ 直链烷基； R³ 是氢或 C₁-C₄ 直链烷基； R⁴ 是吡啶基或咪唑基； 烷基是二价有机基，来源于直链或支链 C₁-C₅ 烷烃；或 其药学上可接受的酸加成盐。 这些化合物可用于阻断中枢或外周羟色胺过量的哺乳动物的 5HT₂ 受体。
• 5ht2c Receptor antagonists in the treatment of schizophrenia
  申请人：Bruinvels T. Anne

  公开号：US20060229299A1

  公开（公告）日：2006-10-12

  The present invention relates to the use of certain 5-HT2C receptor antagonists in the manufacture of medicaments for the treatment of mental disorders, in particular aspects of schizophrenia, cognitive impairment and suicidality, as well as to methods for determining the suitability of compounds for such a use.

  本发明涉及某些 5-HT2C 受体拮抗剂在制造治疗精神疾病，特别是精神分裂症、认知障碍和自杀等方面的药物中的用途，以及确定化合物是否适用于这种用途的方法。