8-methoxy-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one | 165530-13-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯氮卓类
• 英文名称: 8-methoxy-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one
• 英文别名: 8-methoxy-2,3,4,5-tetrahydro-3-oxo-1H-2-benzazepine；8-Methoxy-1,2,4,5-tetrahydrobenzo[c]azepin-3-one；8-methoxy-1,2,4,5-tetrahydro-2-benzazepin-3-one
• CAS: 165530-13-2
• 化学式: C₁₁H₁₃NO₂
• mdl: MFCD00512059
• 分子量: 191.23
• InChiKey: SMPWDVMRQOWAKV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  8-methoxy-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one 在 硼烷 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到8-methoxy-2,3,4,5-tetrahydro-1H-2-benzazepine hydrochloride
  参考文献：
  名称：

  SAR studies of capsazepinoid bronchodilators. Part 1: The importance of the catechol moiety and aspects of the B-ring structure

  摘要：

  Capsazepine as well as its derivatives and analogues are general inhibitors of constriction of human small airways. From a systematic variation of the capsazepine structure, divided into four regions, SARs were established. This part concerns the catechol moiety of the A-ring as well as the 2,3,4,5-tetrahydro-1H-2-azepine moiety (the B-ring) of capsazepine. It is revealed that a conformational constrain (as a fused ring) is important and that compounds with a six-membered B-ring (as a 1,2,3,4-tetrahydroisoquinoline) in general are more potent than the corresponding isoindoline, 2,3,4,5 -tetrahydro-1H-2-benzazepi ne and 2,3,4,5-tetrahydro-1H-3-benzazepine derivatives. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.11.055
• 作为产物：
  描述：

  3,3-Dimethoxy-N-(3-methoxybenzyl)propanamide 在 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 以59%的产率得到8-methoxy-1,2,4,5-tetrahydro-3H-2-benzazepin-3-one
  参考文献：
  名称：

  Aryl-and heteroaryl-substituted tetrahydrobenzazepines and use thereof to block reuptake of norepinephrine, dopamine, and serotonin

  摘要：

  本发明的化合物由以下具有式I(A-E)和式(II)的芳基和杂芳基取代的四氢苯并哌啶和二氢苯并哌啶衍生物表示：其中指定为*的碳原子处于R或S构型，取代基X和R1-R9如本文所定义。

  公开号：

  US20070021408A1

文献信息

• Synthesis and biological evaluation of N-alkylated 8-oxybenz[c]azepine derivatives as selective PPARδ agonists
  作者：Christopher A. Luckhurst、Marianne Ratcliffe、Linda Stein、Mark Furber、Sara Botterell、David Laughton、Wendy Tomlinson、Richard Weaver、Kamaldeep Chohan、Andrew Walding

  DOI：10.1016/j.bmcl.2010.10.083

  日期：2011.1

  We describe the discovery of small molecule benzazepine derivatives as agonists of human peroxisome proliferator-activated receptor delta (PPAR delta) that displayed excellent selectivity over the PPAR delta and PPAR gamma subtypes. Compound 8 displayed good PK in the rat and efficacy in upregulation of pyruvate dehydrogenase kinase, isozyme 4 (PDK4) mRNA in human primary myotubes, a biomarker for increased fatty acid oxidation. (C) 2010 Elsevier Ltd. All rights reserved.
• BICYCLIC FIBRINOGEN ANTAGONISTS
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP0674623A1

  公开（公告）日：1995-10-04
• US6403578B1
  申请人：——

  公开号：US6403578B1

  公开（公告）日：2002-06-11
• [EN] BICYCLIC FIBRINOGEN ANTAGONISTS<br/>[FR] ANTAGONISTES BICYCLIQUES DU FIBRINOGENE
  申请人：——

  公开号：WO1994014776A2

  公开（公告）日：1994-07-07

  [EN] This invention relates to compounds of formulae (I), (II), (II), wherein A<1> is O, S, N-R<1> or CHR<1>; A<4> is N-R<4> or CHR<4>; R<2> is a sidechain containing an acid or ester group; R<1>, R<4> and R<5> are substituents such as H, alkyl and aryl alkyl, and R<6> is a sidechain containing a nitrogen group; and pharmaceutically acceptable salts thereof, which are effective for inhibiting platelet aggregation, pharmaceutical compositions for effecting such activity, and a method for inhibiting platelet aggregation.
  [FR] L'invention concerne des composés des formules (I), (II), (III), dans lesquelles A1 représente, O, S, N-R1 ou CHR1; A4 représente N-R4 ou CHR4, R2 représente une chaîne latérale contenant un groupe acide ou ester, R1, R4 et R5 représentent des substituants tels que H, alkyle et aryle alkyle, et R6 représente une chaîne latérale contenant un groupe azote et leurs sels pharmaceutiquement acceptables, lesquels composés sont efficaces pour inhiber l'aggrégation plaquettaire. L'invention concerne également des compositions pharmaceutiques mettant en oeuvre ladite activité, ainsi qu'un procédé d'inhibition de l'aggrégation plaquettaire.