6-bromo-7,8-dimethoxy-3-[4-(2-methyl-3-phenylallyl)piperazin-1-ylmethyl]-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-bromo-7,8-dimethoxy-3-[4-(2-methyl-3-phenylallyl)piperazin-1-ylmethyl]-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole
• 英文别名: 6-bromo-7,8-dimethoxy-3-[[4-[(E)-2-methyl-3-phenylprop-2-enyl]piperazin-1-yl]methyl]-3a,4-dihydro-3H-chromeno[4,3-c][1,2]oxazole
• 化学式: C₂₇H₃₂BrN₃O₄
• 分子量: 542.473
• InChiKey: YBUNKZFICCGATE-QGOAFFKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-bromo-7,8-dimethoxy-3-[4-(2-methyl-3-phenylallyl)piperazin-1-ylmethyl]-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole 、 碳酸二乙酯 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 3.0h， 以8%的产率得到7,8-dimethoxy-3-[4-(2-methyl-3-phenylallyl)piperazin-1-ylmethyl]-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole-6-carboxylic acid ethyl ester
  参考文献：
  名称：

  [EN] C6- AND C9-SUBSTITUTED '4, 3-C! ISOXAZOLINE DERIVATIVES AND THEIR USE AS ANTI-DEPRESSANTS
  [FR] DERIVES D'ISOXAZOLINE SUBSTITUES EN C6 ET C9 ET UTILISATION DE CEUX-CI COMME ANTIDEPRESSEURS

  摘要：

  公开号：

  WO2004018482A3
• 作为产物：
  描述：

  N-(2-methyl-3-phenyl-2(E)-propen-1-yl)piperazine 、 methanesulfonic acid 6-bromo-7,8-dimethoxy-3a,4-dihydro-3H-chromeno[4,3-c]isoxazol-3-ylmethyl ester 在 potassium carbonate 、 potassium iodide 作用下， 以 4-甲基-2-戊酮 为溶剂， 反应 24.0h， 以83%的产率得到6-bromo-7,8-dimethoxy-3-[4-(2-methyl-3-phenylallyl)piperazin-1-ylmethyl]-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole
  参考文献：
  名称：

  [EN] C6- AND C9-SUBSTITUTED '4, 3-C! ISOXAZOLINE DERIVATIVES AND THEIR USE AS ANTI-DEPRESSANTS
  [FR] DERIVES D'ISOXAZOLINE SUBSTITUES EN C6 ET C9 ET UTILISATION DE CEUX-CI COMME ANTIDEPRESSEURS

  摘要：

  公开号：

  WO2004018482A3

文献信息

• C6- AND C9-SUBSTITUTED CHROMENO[4,3-c]ISOXAZOLINE DERIVATIVES AND THEIR USE AS ANTI-DEPRESSANTS
  申请人：Janssen Pharmaceutica NV

  公开号：EP1532155B1

  公开（公告）日：2008-02-27
• C6- AND C9-SUBSTITUTED CHROMENO[4,3-C]ISOXAZOLINE DERIVATIVES AND THEIR USE AS ANTI-DEPRESSANTS
  申请人：JANSSEN PHARMACEUTICA N.V.

  公开号：EP1532155A2

  公开（公告）日：2005-05-25
• C6-and c9-substituted isoxazoline derivatives and their use as anti-depressants
  申请人：Andres-Gil Ignacio Jose

  公开号：US20060122167A1

  公开（公告）日：2006-06-08

  The invention concerns substituted tricyclic isoxazoline derivatives, more in particular tricyclic dihydrobenzopyranoisoxazoline, dihydroquinolinoisoxazoline, dihydronaphthalenoisoxazoline and dihydrobenzothiopyranoisoxazoline derivatives substituted on at least one of the C6- and C9-positions of the phenylpart of the tricyclic moiety with a selected radical, according to Formula (I) wherein X═CH 2 , N—R 7 , S or O, R 1 , R 2 , R 14 and R 15 are certain specific substituents, with the proviso that at least one of R 14 and R 15 is not hydrogen, Pir is preferably an optionally substituted piperidinyl or piperazinyl radical and R 3 represents an optionally substituted aromatic homocyclic or heterocyclic ring system including a partially or completely hydrogenated hydrocarbon chain of maximum 6 atoms long with which the ring system is attached to the Pir radical and which may contain one or more heteroatoms selected from the group of O, N and S; a process for their preparation, pharmaceutical compositions comprising them and their use as a medicine, in particular for the treatment of depression, anxiety, movement disorders, psychosis, Parkinson's disease and body weight disorders. The compounds according to the invention have surprisingly been shown to have a serotonine (5-HT) reuptake inhibitor activity in combination with additional α 2 -adrenoceptor antagonist activity and show a strong anti-depressant activity without being sedative. The invention also relates to novel combination of isoxazoline derivatives according to the invention with one or more other compounds selected from the group of antidepressants, anxiolytics, anti-psychotics and anti-Parkinson's disease drugs to improve efficacy and/or onset of action.
• US7462717B2
  申请人：——

  公开号：US7462717B2

  公开（公告）日：2008-12-09
• [EN] C6- AND C9-SUBSTITUTED '4, 3-C! ISOXAZOLINE DERIVATIVES AND THEIR USE AS ANTI-DEPRESSANTS<br/>[FR] DERIVES D'ISOXAZOLINE SUBSTITUES EN C6 ET C9 ET UTILISATION DE CEUX-CI COMME ANTIDEPRESSEURS
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2004018482A3

  公开（公告）日：2004-04-01