1-(benzo[b]thiophen-3-yl)-2-bromopropan-1-one | 79156-10-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 1-(benzo[b]thiophen-3-yl)-2-bromopropan-1-one
• 英文别名: 1-(1-Benzothiophen-3-yl)-2-bromopropan-1-one
• CAS: 79156-10-8
• 化学式: C₁₁H₉BrOS
• 分子量: 269.162
• InChiKey: UMVKRWPSCNUOOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  45.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(benzo[b]thiophen-3-yl)-2-bromopropan-1-one 在 盐酸 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 乙酸乙酯 、 乙腈 为溶剂， 反应 1.0h， 生成 1-(benzo[b]thiophen-3-yl)-2-(4-benzyl-5,6-dihydropyridin-1(2H)-yl)propan-1-one hydrochloride
  参考文献：
  名称：

  Synthesis and antidepressant activity of arylalkanol-piperidine derivatives as triple reuptake inhibitors

  摘要：

  A series of arylalkanol-piperidine derivatives was synthesized, and their triple reuptake inhibition and in vivo activities have been evaluated. Among them, compounds 2a, 2j, 2k, 2m and 2n exhibited high potency for 5-HT, NA and DA transporters. Optimized compounds 2j and 2m showed significant reduction of immobility time compared to that of vehicle in the mouse tail suspension test (TST) test at doses ranging from 10 to 50 mg/kg po, and were not generally motor stimulants at 50 mg/kg dose. In addition, compounds 2j and 2m displayed desirable pharmacokinetic properties in SD rats. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.04.030
• 作为产物：
  描述：

  3-丙酰基苯并(b)噻吩 在 copper(ll) bromide 作用下， 以 氯仿 、 乙酸乙酯 为溶剂， 反应 4.0h， 以83.2%的产率得到1-(benzo[b]thiophen-3-yl)-2-bromopropan-1-one
  参考文献：
  名称：

  Synthesis and antidepressant activity of arylalkanol-piperidine derivatives as triple reuptake inhibitors

  摘要：

  A series of arylalkanol-piperidine derivatives was synthesized, and their triple reuptake inhibition and in vivo activities have been evaluated. Among them, compounds 2a, 2j, 2k, 2m and 2n exhibited high potency for 5-HT, NA and DA transporters. Optimized compounds 2j and 2m showed significant reduction of immobility time compared to that of vehicle in the mouse tail suspension test (TST) test at doses ranging from 10 to 50 mg/kg po, and were not generally motor stimulants at 50 mg/kg dose. In addition, compounds 2j and 2m displayed desirable pharmacokinetic properties in SD rats. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.04.030

文献信息

• BENZOTHIOPHENE ALKANOL PIPERAZINE DERIVATIVES AND THEIR USE AS ANTIDEPRESSANT
  申请人：Li Jianqi

  公开号：US20110118263A1

  公开（公告）日：2011-05-19

  The invention discloses benzothiophene alkanol piperazine derivatives and their use as antidepressants. The invention discloses the said benzothiophene alkanol piperazine derivative having triple inhibition effect on the reuptake of 5-HT, NA and DA. Compared with clinical used antidepressants so far having single target, e.g. desipramine and fluoxetine, and clinical used antidepressants so far having double targets, e.g venlafaxine and duloxetine, the said benzothiophene alkanol piperazine derivatives of the present invention may have a broader indication range and less toxic and side effects to nervous system. The benzothiophene alkanol piperazine derivatives are the compounds with the following formula or their pharmaceutically acceptable salts, wherein Ar 1 , R 1 -R 4 , X, Y, m and n have the same definition as defined in claim 1.

  该发明披露了苯并噻吩烷醇哌嗪衍生物及其作为抗抑郁药物的用途。该发明揭示了所述苯并噻吩烷醇哌嗪衍生物对5-HT、NA和DA的再摄取具有三重抑制效应。与迄今为止具有单一靶点的临床使用抗抑郁药物（如去甲丙胺和氟西汀）以及迄今为止具有双重靶点的临床使用抗抑郁药物（如文拉法辛和度洛西汀）相比，本发明的苯并噻吩烷醇哌嗪衍生物可能具有更广泛的适应症范围，对神经系统的毒性和副作用更少。苯并噻吩烷醇哌嗪衍生物是具有以下结构式或其药用盐的化合物，其中Ar1、R1-R4、X、Y、m和n的定义与权利要求1中定义的相同。
• SUBSTITUTED IMIDAZOTHIAZOLES AS ANTIDEPRESSANT AGENTS
  申请人：Knoll GmbH

  公开号：EP1187836A1

  公开（公告）日：2002-03-20
• US8680097B2
  申请人：——

  公开号：US8680097B2

  公开（公告）日：2014-03-25
• [EN] SUBSTITUTED IMIDAZOTHIAZOLES AS ANTIDEPRESSANT AGENTS<br/>[FR] IMIDAZOTHIAZOLES SUBSTITUES UTILISES EN TANT QU'AGENTS ANTIDEPRESSIFS
  申请人：KNOLL AG

  公开号：WO2000071548A1

  公开（公告）日：2000-11-30

  Compounds of Formula (I) including pharmaceutically acceptable salts thereof, in which A is S or O; R1 is H, halo, a C1-3 alkyl group or a C1-3 alkylthio group; R2 is H or fluoro; and R3 is methyl, ethyl or isopropyl are useful in the treatment of depression, anxiety, psychoses (for example schizophrenia), tardive dyskinesia, obesity, drug addiction, drug abuse, cognitive disorders, Alzheimer's disease, cerebral ischaemia, obsessive-compulsive behaviour, panic attacks, social phobias, eating disorders such as bulimia, anorexia, snacking and binge eating, non-insulin dependent diabetes mellitus, hyperglycaemia, hyperlipidaemia, stress and in the treatment and/or prophylaxis of seizures, neurological disorders such as epilepsy and/or conditions in which there is neurological damage such as stroke, brain trauma, cerebral ischaemia, head injuries and haemorrhage.
• Synthesis and antidepressant activity of arylalkanol-piperidine derivatives as triple reuptake inhibitors
  作者：Yong-Yong Zheng、Lin Guo、Xue-Chu Zhen、Jian-Qi Li

  DOI：10.1016/j.ejmech.2012.04.030

  日期：2012.8

  A series of arylalkanol-piperidine derivatives was synthesized, and their triple reuptake inhibition and in vivo activities have been evaluated. Among them, compounds 2a, 2j, 2k, 2m and 2n exhibited high potency for 5-HT, NA and DA transporters. Optimized compounds 2j and 2m showed significant reduction of immobility time compared to that of vehicle in the mouse tail suspension test (TST) test at doses ranging from 10 to 50 mg/kg po, and were not generally motor stimulants at 50 mg/kg dose. In addition, compounds 2j and 2m displayed desirable pharmacokinetic properties in SD rats. (C) 2012 Elsevier Masson SAS. All rights reserved.