(4aR,10bR)-8-(2-hydroxyethyl)-N,N-diethyl-4-propyl-3,4,4a,5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazine-9-carboxamide | 1015214-50-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (4aR,10bR)-8-(2-hydroxyethyl)-N,N-diethyl-4-propyl-3,4,4a,5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazine-9-carboxamide
• 英文别名: (4aR,10bR)-N,N-diethyl-8-(2-hydroxyethyl)-4-propyl-2,3,4a,5,6,10b-hexahydrobenzo[h][1,4]benzoxazine-9-carboxamide
• CAS: 1015214-50-2
• 化学式: C₂₂H₃₄N₂O₃
• 分子量: 374.524
• InChiKey: SMKCNDUDSGSWRD-NHCUHLMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  27
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  53
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4aR,10bR)-8-(2-hydroxyethyl)-N,N-diethyl-4-propyl-3,4,4a,5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazine-9-carboxamide 在 盐酸 作用下， 以 水 为溶剂， 以57%的产率得到(4aR,12bR)-4-propyl-2,3,4a,5,6,8,9,12b-octahydroisochromeno[6,7-h][1,4]benzoxazin-11-one
  参考文献：
  名称：

  Modulations of the amide function of the preferential dopamine D3 agonist (R,R)-S32504: Improvements of affinity and selectivity for D3 versus D2 receptors

  摘要：

  Starting with the preferential dopamine (DA) D(3) agonist S32504, we prepared two series of derivatives of the general formula I-A and I-B, in an effort to improve both potency and selectivity. For the first set of derivatives, where the primary amide function of S32504 was replaced by either secondary and tertiary amide or ester, acid, nitrile and ketone, no improvement was obtained. Conversely, when the primary amide function was integrated in a lactam ring, an enhancement of affinity and selectivity was attained for the five-membered ring lactam but also for its five-membered ring lactone analogue. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.015
• 作为产物：
  描述：

  2-溴乙醇 在 四甲基乙二胺 、 仲丁基锂 、 正丁基锂 、 水 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.08h， 生成 (4aR,10bR)-8-(2-hydroxyethyl)-N,N-diethyl-4-propyl-3,4,4a,5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazine-9-carboxamide
  参考文献：
  名称：

  Tetracyclic compounds

  摘要：

  式I的化合物，具有反式相对构型： 其中： X代表氧原子或NR2基团， Y代表从—CH2—，—（CH2）2—和—CH═CH—中选择的基团， R1和R2，可以相同也可以不同，每个代表氢原子或从烷基，环烷基和环烷基烷基中选择的基团， 以外消旋形式或光学异构体形式存在的药物，以及其与药学上可接受的酸的加合物和水合物。 含有这种化合物的药物，对涉及多巴胺能系统的中枢神经系统疾病的治疗非常有用。

  公开号：

  US20080076765A1

文献信息

• US7470683B2
  申请人：——

  公开号：US7470683B2

  公开（公告）日：2008-12-30
• Modulations of the amide function of the preferential dopamine D3 agonist (R,R)-S32504: Improvements of affinity and selectivity for D3 versus D2 receptors
  作者：Jean-Louis Peglion、Christophe Poitevin、Clotilde Mannoury La Cour、Delphine Dupuis、Mark J. Millan

  DOI：10.1016/j.bmcl.2009.03.015

  日期：2009.4

  Starting with the preferential dopamine (DA) D(3) agonist S32504, we prepared two series of derivatives of the general formula I-A and I-B, in an effort to improve both potency and selectivity. For the first set of derivatives, where the primary amide function of S32504 was replaced by either secondary and tertiary amide or ester, acid, nitrile and ketone, no improvement was obtained. Conversely, when the primary amide function was integrated in a lactam ring, an enhancement of affinity and selectivity was attained for the five-membered ring lactam but also for its five-membered ring lactone analogue. (C) 2009 Elsevier Ltd. All rights reserved.
• Tetracyclic compounds
  申请人：Peglion Jean-Louis

  公开号：US20080076765A1

  公开（公告）日：2008-03-27

  Compounds of formula I, of trans relative configuration: wherein: X represents an oxygen atom or an NR 2 group, Y represents a group selected from —CH 2 —, —(CH 2 ) 2 — and —CH═CH—, R 1 and R 2 , which may be the same or different, each represents a hydrogen atom or a group selected from alkyl, cycloalkyl and cycloalkylalkyl, in racemic form or in the form of optical isomers, and also addition salts thereof with a pharmaceutically acceptable acid, and hydrates thereof. Medicinal products containing the same which are useful in the treatment of disorders of the central nervous system that involve the dopaminergic system.

  式I的化合物，具有反式相对构型： 其中： X代表氧原子或NR2基团， Y代表从—CH2—，—（CH2）2—和—CH═CH—中选择的基团， R1和R2，可以相同也可以不同，每个代表氢原子或从烷基，环烷基和环烷基烷基中选择的基团， 以外消旋形式或光学异构体形式存在的药物，以及其与药学上可接受的酸的加合物和水合物。 含有这种化合物的药物，对涉及多巴胺能系统的中枢神经系统疾病的治疗非常有用。