6-methyl-8β-(N-ethoxycarbonylmethyl-aminomethyl)-ergoline | 95688-31-6

• 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: 6-methyl-8β-(N-ethoxycarbonylmethyl-aminomethyl)-ergoline
• 英文别名: 6-methyl-8beta-(N-ethoxycarbonylmethyl-aminomethyl)-ergoline；ethyl 2-[[(6aR,9S,10aR)-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]methylamino]acetate
• CAS: 95688-31-6
• 化学式: C₂₀H₂₇N₃O₂
• 分子量: 341.453
• InChiKey: QOSXQPJDPYCNGQ-FDQGKXFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  57.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-methyl-8β-(N-ethoxycarbonylmethyl-aminomethyl)-ergoline 在 盐酸 、 potassium hydrogencarbonate 、 溶剂黄146 、 锌 作用下， 以 水 、 甲苯 为溶剂， 反应 7.0h， 生成 1-[[(6aR,9R,10aR)-4,6,6a,7,8,9,10,10a-octahydroindolo[4,3-fg]quinolin-9-yl]methyl]imidazolidine-2,4-dione
  参考文献：
  名称：

  2,4-二氧杂咪唑啉-1-基和过氢-2,4-二氧嘧啶丁-1-基麦角灵衍生物的合成及其降压活性。

  摘要：

  报道了一系列2,4-二氧杂咪唑啉-1-基和过氢-2,4-二氧嘧啶亚基-1-基麦角灵衍生物的合成和降压活性。通过在治疗后的不同时间通过间接尾袖法测量收缩压来研究自发性高血压大鼠（SHRs）的口服降压活性。还研究了大鼠的催乳激素降低活性（通过硝化试验间接测定）和小鼠的口服急性毒性。这项研究的结果表明，有效的降压麦角灵衍生物没有与多巴胺能刺激有关的副作用，而且δ9,10双键对于在这些化合物中赋予高效力具有重要意义。

  DOI：

  10.1016/s0014-827x(98)00023-8
• 作为产物：
  描述：

  6-甲基麦角灵-8β-甲醇 在 TEA 、 三苯基膦 、 肼 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 6-methyl-8β-(N-ethoxycarbonylmethyl-aminomethyl)-ergoline
  参考文献：
  名称：

  Serotonergic ergoline derivatives

  摘要：

  Novel classes of 13- and 14-tertbutyl-ergoline derivatives were prepared, and characterised in vitro for their affinity for adrenergic, dopaminergic and serotonergic binding sites. This study particularly examines the importance of the presence and the position of the tert-butyl group in conferring either significant 5-HT1A or 5-HT2 affinity and selectivity respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00166-8

文献信息

• Ergolines exhibiting protactin secretion inhibition activity
  申请人：Farmitalia Carlo Erba

  公开号：US04690929A1

  公开（公告）日：1987-09-01

  Compounds of formula I: ##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, cyano, C.sub.1 -C.sub.4 alkylthio or phenylthio group; R.sub.7 and R.sub.8 represent hydrogen atoms and R.sub.3 represents a hydrogen atom or a methoxy group, or R.sub.7 represents a hydrogen atom and R.sub.3 and R.sub.8 taken together represent a bond, or R.sub.3 represents a hydrogen atom or a methoxy group and R.sub.7 and R.sub.8 taken together represent a bond; R.sub.4 represents a hydrocarbon group having from 1 to 4 carbon atoms; R.sub.5 represents a hydrogen atom or a hydrocarbon group having from 1 to 4 carbon atoms or a phenyl group; X represents an oxygen or sulphur atom or an imino group, R.sub.9 represents a hydrogen atom and B represents a cyano, a C.sub.2 -C.sub.5 alkoxycarbonyl or carbamoyl group, or R.sub.9 and B taken together represent a ##STR2## group wherein W represents an oxygen atom or an imino group; A represents a group of the formula CHR.sub.6, CH.sub.2 --CHR.sub.6 or CH.dbd.CR.sub.6 group wherein R.sub.6 represents a hydrogen atom or a C.sub.1 -C.sub.4 alkyl group; and n is 0, 1 or 2; and their pharmaceutically acceptable salts are disclosed, along with the use of these compounds as antiprolactinic and antihypertensive agents. The preparation of these compounds and pharmaceutical compositions containing them are also described.

  化合物I的公式：##STR1## 其中，R.sub.1代表氢原子或甲基基团；R.sub.2代表氢原子或卤素原子，或甲基，氰基，C.sub.1-C.sub.4烷基硫基或苯基硫基基团；R.sub.7和R.sub.8代表氢原子，R.sub.3代表氢原子或甲氧基，或R.sub.7代表氢原子，R.sub.3和R.sub.8共同代表键，或R.sub.3代表氢原子或甲氧基，R.sub.7和R.sub.8共同代表键；R.sub.4代表具有1至4个碳原子的碳氢基团；R.sub.5代表氢原子或具有1至4个碳原子或苯基的碳氢基团；X代表氧原子或硫原子或亚胺基，R.sub.9代表氢原子，B代表氰基，C.sub.2-C.sub.5烷氧羰基或氨基甲酰基团，或R.sub.9和B共同代表一个##STR2##基团，其中W代表氧原子或亚胺基；A代表公式CHR.sub.6，CH.sub.2--CHR.sub.6或CH.dbd.CR.sub.6基团，其中R.sub.6代表氢原子或C.sub.1-C.sub.4烷基；n为0、1或2；以及它们的药学上可接受的盐，以及这些化合物作为抗催乳素和降压剂的用途。还描述了这些化合物的制备和含有它们的制药组合物。
• Ergoline derivatives, processes for their preparation and pharmaceutical compositions containing same
  申请人：FARMITALIA CARLO ERBA S.r.l.

  公开号：EP0126968A1

  公开（公告）日：1984-12-05

  R1=H, CH3 R2=H, halogen, CH3, CN, lower alkylthio, phenylthio R7 and R8=H; R3=H, OCH3 R7=H, R3 and Rs= bond R7 and R8=bond, R3=H, OCH3 R4=C1-C4 hydrocarbon Rs=H, C1-C4 hydrocarbon, phenyl A=CHR6, CH2CHR6, CH=CR6 R6=H, lower alkyl n=O, 1, 2 X=O,S,NH B=CN, COOalK. CONH2 R9=H or B and R9=-C=W W=O,NH and their pharmaceutically acceptable salts are antiprolacti- nic and antihypertensive agents. Their preparation and pharmaceutical compositions containing them are also described.

  R1=H, CH3 R2=H、卤素、CH3、CN、低级烷硫基、苯硫基 R7 和 R8=H; R3=H, OCH3 R7=H，R3 和 Rs=键 R7 和 R8= 键，R3=H，OCH3 R4=C1-C4 碳氢化合物 Rs=H、C1-C4 碳氢化合物、苯基 A=CHR6，CH2CHR6，CHR6 R6=H、低级烷基 n=O、1、2 X=O,S,NH B=CN, COOalK.CONH2 R9=H 或 B 和 R9=-C=W W=O,NH 及其药学上可接受的盐类是抗催乳和抗高血压药物。此外，还介绍了它们的制备方法和含有它们的药物组合物。
• US4690929A
  申请人：——

  公开号：US4690929A

  公开（公告）日：1987-09-01
• Serotonergic ergoline derivatives
  作者：Sergio Mantegani、Enzo Brambilla、Carla Caccia、Gabriele Damiani、Maria Gioia Fornaretto、Robert A. McArthur、Mario Varasi

  DOI：10.1016/s0960-894x(98)00166-8

  日期：1998.5

  Novel classes of 13- and 14-tertbutyl-ergoline derivatives were prepared, and characterised in vitro for their affinity for adrenergic, dopaminergic and serotonergic binding sites. This study particularly examines the importance of the presence and the position of the tert-butyl group in conferring either significant 5-HT1A or 5-HT2 affinity and selectivity respectively. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Synthesis and antihypertensive activity of 2,4-dioxoimidazolidin-1-yl and perhydro-2,4-dioxopyrimidin-1-yl ergoline derivatives
  作者：Sergio Mantegani、Enzo Brambilla、Carla Caccia、Laura Chiodini、Daniela Ruggieri、Ernesto Lamberti、Enrico Di Salle、Patricia Salvati

  DOI：10.1016/s0014-827x(98)00023-8

  日期：1998.4

  The synthesis and antihypertensive activity of a series of 2,4-dioxoimidazolidin-1-yl and perhydro-2,4-dioxopyrimidin-1-yl ergoline derivatives are reported. The oral antihypertensive activity was studied in spontaneously hypertensive rats (SHRs) by measuring systolic blood pressure by an indirect tail-cuff method at different times after treatment. The prolactin lowering activity (indirectly measured

  报道了一系列2,4-二氧杂咪唑啉-1-基和过氢-2,4-二氧嘧啶亚基-1-基麦角灵衍生物的合成和降压活性。通过在治疗后的不同时间通过间接尾袖法测量收缩压来研究自发性高血压大鼠（SHRs）的口服降压活性。还研究了大鼠的催乳激素降低活性（通过硝化试验间接测定）和小鼠的口服急性毒性。这项研究的结果表明，有效的降压麦角灵衍生物没有与多巴胺能刺激有关的副作用，而且δ9,10双键对于在这些化合物中赋予高效力具有重要意义。