(5R,8R)-8-Amino-6-methyl-9,10-didehydroergolin | 85624-10-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (5R,8R)-8-Amino-6-methyl-9,10-didehydroergolin
• 英文别名: 6-methyl-9,10-didehydroergolin-8β-amine；6-methyl-9,10-didehydro-ergolin-8β-ylamine；9,10-Didehydro-6-methylergoline-8beta-amine；(6aR,9R)-7-methyl-6,6a,8,9-tetrahydro-4H-indolo[4,3-fg]quinolin-9-amine
• CAS: 85624-10-8
• 化学式: C₁₅H₁₇N₃
• 分子量: 239.32
• InChiKey: YFPQZLKFHUVMEA-QMTHXVAHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  45
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (5R,8R)-8-Amino-6-methyl-9,10-didehydroergolin 在 lithium amide 、 氨 、 lithium 、 苯胺 作用下， 以 四氢呋喃 为溶剂， 以71%的产率得到6-甲基麦角灵-8beta-胺
  参考文献：
  名称：

  Reduction of 8α-Substituted 9,10-Didehydroergolines

  摘要：

  DOI：

  10.1055/s-1986-31850
• 作为产物：
  描述：

  lysergic acid-azide; hydrochloride 在 盐酸 、 水 作用下， 生成 (5R,8R)-8-Amino-6-methyl-9,10-didehydroergolin
  参考文献：
  名称：

  关于库尔修斯（Curtius）对麦角酸和二氢麦角酸异构体的降解。（关于麦角生物碱的第十二次交流

  摘要：

  DOI：

  10.1002/hlca.19470300108

文献信息

• Novel ergolinyl compounds nitrogen-substituted in the 8-position, useful
  申请人：Schering Aktiengesellschaft

  公开号：US04826852A1

  公开（公告）日：1989-05-02

  Ergolinyl compounds which are nitrogen-substituted in the 8-position and have Formula (I) ##STR1## and physiologically compatible salts thereof, wherein (a) R.sup.1 is hydrogen, the 8-substituent can be in the .alpha.- or .beta.-position and ##STR2## represents a single or a double bond, R.sup.2 is hydrogen, C.sub.1-4 -alkyl or C.sub.1-7 -acyl, R.sup.3 is hydrogen, chlorine or bromine, and R.sup.4 is C.sub.1-6 -alkyl, C.sub.3-6 -cycloalkyl-C.sub.1-3 -alkyl, C.sub.3-6 -alkenyl, or C.sub.3-6 -alkynyl; or (b) R.sup.1 is ##STR3## and the 8-substituent can be in the .alpha.- or .beta.-position, ##STR4## represents a single or double bond, R.sup.2, R.sup.3 are as defined above, R.sup.4, is C.sub.1.varies.6 -alkyl, C.sub.3-6 -cycloalkyl-C.sub.1-3 -alkyl, C.sub.3-6 -alkenyl, or C.sub.3-6 -alkynyl; and R.sup.5 is hydrogen, C.sub.-10 -alkyl, C.sub.3-10 -alkenyl, or C.sub.3-10 -alkynyl, and R.sup.6 is C.sub.1-10 -alkyl, C.sub.3-10 -alkenyl, C.sub.3-10 -alkynyl, or aryl, or R.sup.5 and R.sup.6 together with the connecting N-atom form a 5- to 10-membered heterocyclic ring, preferably 5- or 6-membered, which optionally can contain further heteroatoms.

  8-位氮取代的Ergolinyl化合物及其生理相容盐，其化学式为(I) ##STR1## 其中(a) R.sup.1为氢，8-取代基可以在α-或β-位置，##STR2##表示单键或双键，R.sup.2为氢，C.sub.1-4 -烷基或C.sub.1-7 -酰基，R.sup.3为氢，氯或溴，R.sup.4为C.sub.1-6 -烷基，C.sub.3-6 -环烷-C.sub.1-3 -烷基，C.sub.3-6 -烯基或C.sub.3-6 -炔基;或(b) R.sup.1为##STR3##，8-取代基可以在α-或β-位置，##STR4##表示单键或双键，R.sup.2，R.sup.3如上所述，R.sup.4为C.sub.1-6 -烷基，C.sub.3-6 -环烷-C.sub.1-3 -烷基，C.sub.3-6 -烯基或C.sub.3-6 -炔基；R.sup.5为氢，C.sub.-10 -烷基，C.sub.3-10 -烯基或C.sub.3-10 -炔基，R.sup.6为C.sub.1-10 -烷基，C.sub.3-10 -烯基，C.sub.3-10 -炔基或芳基，或R.sup.5和R.sup.6与连接的N原子一起形成5-至10-成员的杂环环，优选为5-或6-成员，该环可选地含有进一步的杂原子。
• Novel ergolinyl compounds nitrogen-substituted in the 8-position, their preparation, and use as medicinal agents
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0082808A1

  公开（公告）日：1983-06-29

  Ergolinyl compounds which are nitrogen-substituted in the 8-position and have Formula (I) and physiologically compatible salts thereof, wherein (a) R1 is hydrogen, the 8-substituent can be in the a- or β-position and represents a single or a double bond, R2 is hydrogen, C1 4-alkyl or C1 7-acyl, R3 is hydrogen, chlorine or bromine, and R4 is C1-6-alkyl, C3-6-cycloalkyl-C1-3-alkyl, C3 6-alkenyl, or C3-6-alkynyl; or (b) R1 is and the 8-substituent can be in the a- or β-position, represents a single or double bond, R2, R3 are as defined above, R4, is C1-6-alkyl, C3-6-cycloalkyl-C1-3-alkyl, C3 alkenyl, or C3-6-alkynyl; and R5 is hydrogen, C1 10-alkyl, C3 10-alkenyl, or C3 10- alkynyl, and R6 is C1 10-alkyl, C3-10-alkenyl, C3-10-alkynyl, or aryl, or R5 and R6 together with the connecting N-atom form a 5- to 10-membered heterocyclic ring, preferably 5- or 6- membered, which optionally can contain further heteroatoms

  在 8 位上氮取代且具有式 (I) 的麦角酰基化合物 及其生理相容盐，其中 (a) R1 为氢，8-取代基可以位于 a 位或β位，并且 代表单键或双键、 R2 是氢、C1 4-烷基或 C1 7-酰基、 R3 是氢、氯或溴，以及 R4 是 C1-6-烷基、C3-6-环烷基-C1-3-烷基、C3-6-烯基或 C3-6- 烷炔基；或 (b) R1 是 且 8-取代基可以位于 a 位或β位、 代表单键或双键、 R2、R3 如上定义、 R4 是 C1-6 烷基、C3-6-环烷基-C1-3-烷基、C3 烯基或 C3-6 烷炔基；以及 R5 是氢、C1 10-烷基、C3 10-烯基或 C3 10-炔基，和 R6 是 C1 10-烷基、C3 10-烯基、C3 10-炔基或芳基，或 R5 和 R6 与连接的 N 原子一起形成一个 5 至 10 个成员的杂环，最好是 5 或 6 个成员的杂环，其中可选择包含更多的杂原子
• Process for the preparation of ergoline derivatives
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0074921A1

  公开（公告）日：1983-03-23

  A process for preparing an ergoline of the formula wherein Cs = C10 is a CC single or double bond, R' is a hydrogen or CONR2, R being hydrogen, methyl, or ethyl, and wherein NR' is in the a- or β-position, R2 is lower alkyl of up to 3 carbon atoms, and the salts thereof, comprises treating the corresponding ergolinyl carboxylic acid amide with lead (IV) acetate in an aprotic polar solvent; reacting the intermediarily formed corresponding isocyanate with water or with a reactive amine of up to 4 carbon atoms, (e.g. a mono- or dialkylamine of up to 4-C atoms); and, optionally, treating the resultant product with an acid to form the corresponding salt.

  一种制备式中Cs＝C10为CC单键或双键，R'为氢或CONR2，R为氢、甲基或乙基，其中NR'位于a位或β位，R2为不超过3个碳原子的低级烷基的麦角啉及其盐的工艺，包括在非沸腾极性溶剂中用乙酸铅（IV）处理相应的麦角啉基羧酸酰胺；将中间形成的相应异氰酸酯与水或不超过4个碳原子的活性胺（例如不超过4-C原子的单烷基胺或二烷基胺）反应；以及任选地，用酸处理所得产物以形成相应的盐。
• D1 Agonist and/or D2 antagonist dopamine receptor properties of a series of ergoline derivatives: a structure–activity study
  作者：Sergio Mantegani、Emanuele Arlandini、Tiziano Bandiera、Daniela Borghi、Enzo Brambilla、Carla Caccia、Maria Antonietta Cervini、Paolo Cremonesi、Robert Albert McArthur、Gabriella Traquandi、Mario Varasi

  DOI：10.1016/s0223-5234(99)80045-2

  日期：1999.2

  A series of (3,5-dioxopiperazin-1-yl)ergoline derivatives has been synthesised and evaluated in vitro and in vivo for their dopaminergic D-1 and D-2 components. The structural contributions to the pharmacological profile of the ergoline skeleton, its substituents on positions 1, 2, 6, 9, and the 3,5-dioxopiperazin-1-yl portion of the molecule were examined. Structure-activity relationships within this series suggested that substitution on the ergoline skeleton in position 1 or 2 and on the 3,5-dioxopiperazin-4-nitrogen generated compounds with a spectrum of dopamine agonistic/antagonistic activity sensitive to both the nature and position of substituents. (C) Elsevier, Paris.
• US4748248A
  申请人：——

  公开号：US4748248A

  公开（公告）日：1988-05-31