6-(2-propenyl)-9,10-dihydrolysergic acid methyl ester | 72821-79-5

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 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: 6-(2-propenyl)-9,10-dihydrolysergic acid methyl ester
• 英文别名: cabergolinic acid methyl ester；methyl (6aR,9R,10aR)-7-allyl-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinoline-9-carboxylate；D-6-allyl-8β-methoxycarbonylergoline；methyl 6-(2-propenyl)-ergoline-8β-carboxylate；6-Allyl-8b-carboxyergoline Methyl Ester；methyl (6aR,9R,10aR)-7-prop-2-enyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinoline-9-carboxylate
• CAS: 72821-79-5
• 化学式: C₁₉H₂₂N₂O₂
• 分子量: 310.396
• InChiKey: IACRGBGBDYCBKO-FRFSOERESA-N

物化性质

• 沸点：
  474.1±45.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（微量）、甲醇（微量）、吡啶（微量）

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  6-(2-propenyl)-9,10-dihydrolysergic acid methyl ester 以 溶剂黄146 、 甲苯 为溶剂， 生成 卡麦角林
  参考文献：
  名称：

  Synthèse et activité inhibitrice sur la nidation d'une nouvelle classe de dérivés de l'ergoline

  摘要：

  DOI：

  10.1016/0223-5234(89)90087-1
• 作为产物：
  描述：

  二氢麦角隐亭 在 4-二甲氨基吡啶 、 sodium dithionite 、 硫酸 、 potassium carbonate 、 sodium hydroxide 、 锌 作用下， 以 甲醇 、 二氯甲烷 、 水 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.58h， 生成 6-(2-propenyl)-9,10-dihydrolysergic acid methyl ester
  参考文献：
  名称：

  Synthesis of European pharmacopoeial impurities A, B, C, and D of cabergoline

  摘要：

  为了使用分析技术，合成了欧洲药典中提到的卡贝缩脲的杂质A、B、C和D。选择了麦角隐碱作为起始材料，合成通过两种不同的途径完成，长度和立体化学结果各异。较长的间接途径通过对9,10-二氢麦角酰的衍生物进行问题较多的氧化反应，得到相应的醛和羧酸。通过使用活化的DMSO和Pinnick氧化序列实现了这一过程。所有四种合成的杂质均用于卡贝缩脲生产过程中作为分析标准。

  DOI：

  10.1039/c3ra43417f

文献信息

• New and efficient process for the preperation of cabergoline and its intermediates
  申请人：Wang Zhi-Xian

  公开号：US20080275240A1

  公开（公告）日：2008-11-06

  This invention relates to a new and efficient process for the production of dopamine agonists such as Cabergoline and the intermediates thereof.

  这项发明涉及一种用于生产多巴胺激动剂（如卡贝哌酮）及其中间体的新型高效工艺。
• 6-N-Propyl-8-methoxymethyl or methylmercaptomethylergolines and related
  申请人：Eli Lilly and Company

  公开号：US04166182A1

  公开（公告）日：1979-08-28

  6-n-Propyl (ethyl or allyl)-8.beta.-methoxy-(methylsulfinyl, methylsulfonyl, or methylmercapto) methylergolines, 8-ergolenes or 9-ergolenes, useful as prolactin inhibitors and in the treatment of Parkinsonism.

  6-正丙基（乙基或烯丙基）-8-β-甲氧基-（甲磺酰基、甲砜基或甲硫基）甲基麦角碱，8-麦角酚或9-麦角酚，可用作催乳素抑制剂并用于帕金森病的治疗。
• Ergoline compounds, their preparation and pharmaceutical compositions containing them
  申请人：ELI LILLY AND COMPANY

  公开号：EP0003667A1

  公开（公告）日：1979-08-22

  Novel ergoline compounds of the following formula are described: wherein R1 is ethyl, n-propyl, or allyl; Y is O, S, SO, or SO2; X is hydrogen, chloro, or bromo; the dotted line represents the optional presence of a double bond; and the pharmaceutically-acceptable acid addition salts thereof. The compounds are useful to inhibit prolactin secretion or to treat Parkinson's syndrome.

  描述了下式的新型麦角啉化合物： 其中 R1 是乙基、正丙基或烯丙基；Y 是 O、S、SO 或 SO2；X 是氢、氯或溴；虚线表示任选存在的双键；及其药学上可接受的酸加成盐。这些化合物可用于抑制催乳素分泌或治疗帕金森综合症。
• Synthesis of Novel Analogs of Cabergoline: Improving Cardiovascular Safety by Removing 5-HT_2B Receptor Agonism
  作者：Peter I. Dosa、Tim Ward、Michael A. Walters、Suck Won Kim

  DOI：10.1021/ml3003814

  日期：2013.2.14

  The dopamine agonist cabergoline has been used to treat prolactinomas, Parkinson's disease, Cushing's disease, and sexual dysfunction. However, its clinical use was severely curtailed when it was found that patients taking cabergoline had an increased risk of developing cardiac-valve regurgitation. This potentially life-threatening condition has been associated with drugs, such as cabergoline, that are 5-HT2B receptor agonists. We prepared analogs of cabergoline and have identified several that have limited or no agonism at the 5-HT2B receptor.
• A Practical Synthesis of Cabergoline
  作者：Scott W. Ashford、Kevin E. Henegar、Andrew M. Anderson、Peter G. M. Wuts

  DOI：10.1021/jo0203847

  日期：2002.10.1

  Cabergoline is an N-acylurea derived from 9,10-dihydrolysergic acid, which is a potent prolactin inhibitor. It is marketed by Pharmacia as Dostinex for the treatment of hyperprolactinemia and is currently under active development for the treatment of a variety of CNS disorders. In the existing process, the N-acylurea is formed by the reaction of an amide with a large excess of ethyl isocyanate at elevated temperatures. An improved process was developed that eliminates this hazardous reaction. The amide is reacted with phenyl chloroformate and then with ethylamine, which provides a mild and efficient means of forming the unsymmetrical N-acylurea.