6-methyl-8β-benzoylaminomethyl-13-tert-butyl-ergoline | 157767-06-1

• 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-benzoylaminomethyl-13-tert-butyl-ergoline
• 英文别名: N-((6aR,9S,10aR)-2-tert-Butyl-7-methyl-4,6,6a,7,8,9,10,10a-octahydro-indolo[4,3-fg]quinolin-9-ylmethyl)-benzamide；N-[[(6aR,9S,10aR)-2-tert-butyl-7-methyl-6,6a,8,9,10,10a-hexahydro-4H-indolo[4,3-fg]quinolin-9-yl]methyl]benzamide
• CAS: 157767-06-1
• 化学式: C₂₇H₃₃N₃O
• 分子量: 415.579
• InChiKey: OJMHZETUZYJZAI-XVWGUNQUSA-N

物化性质

• 沸点：
  629.8±50.0 °C(Predicted)
• 密度：
  1.133±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  48.1
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-methyl-8β-benzoylaminomethyl-13-tert-butyl-ergoline 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以53%的产率得到2-bromo-6-methyl-8β-benzoylaminomethyl-13-tert-butyl-ergoline
  参考文献：
  名称：

  Synthesis and in vitro structure-activity relationship of 13-tert-butyl-ergoline derivatives as 5-HT1A receptor ligands

  摘要：

  A series of novel 13-tert-butyl-ergoline derivatives was prepared and evaluated for affinity to adrenergic, dopaminergic and serotonergic receptor sites. Selectivity for 5-HT1A receptors versus alpha(1), alpha(2), D-1, D-2, and 5-HT2 appears to be influenced by the presence of the tert-butyl moiety at position 13 of the ergoline skeleton. Some compounds within this series display nanomolar 5-HT1A affinity and hundred-fold selectivity versus the other receptors considered.

  DOI：

  10.1016/s0223-5234(99)80065-8
• 作为产物：
  描述：

  9,10-dihydrolysergic acid methyl ester 在 sodium tetrahydroborate 、 TEA 、 镍 、 三苯基膦 、 三氟乙酸 、 肼 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 6-methyl-8β-benzoylaminomethyl-13-tert-butyl-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

• SEROTONINERGIC ERGOLINE DERIVATIVES
  申请人：PHARMACIA & UPJOHN S.p.A.

  公开号：EP0628042B1

  公开（公告）日：2001-08-16
• US5430031A
  申请人：——

  公开号：US5430031A

  公开（公告）日：1995-07-04
• 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 in vitro structure-activity relationship of 13-tert-butyl-ergoline derivatives as 5-HT1A receptor ligands
  作者：S Mantegani、E Brambilla、C Caccia、MG Fornaretto、RA Mc Arthur、M Varasi

  DOI：10.1016/s0223-5234(99)80065-8

  日期：1997.10

  A series of novel 13-tert-butyl-ergoline derivatives was prepared and evaluated for affinity to adrenergic, dopaminergic and serotonergic receptor sites. Selectivity for 5-HT1A receptors versus alpha(1), alpha(2), D-1, D-2, and 5-HT2 appears to be influenced by the presence of the tert-butyl moiety at position 13 of the ergoline skeleton. Some compounds within this series display nanomolar 5-HT1A affinity and hundred-fold selectivity versus the other receptors considered.