2-bromo-3',5'-difluoropropiophenone | 135306-46-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromo-3',5'-difluoropropiophenone
• 英文别名: 2-bromo-1-(3,5-difluorophenyl)propan-1-one
• CAS: 135306-46-6
• 化学式: C₉H₇BrF₂O
• 分子量: 249.055
• InChiKey: OBQPRZTXLWAVSU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromo-3',5'-difluoropropiophenone 在 2,6-二甲基吡啶 、 sodium hydroxide 作用下， 以 乙醚 、 乙腈 为溶剂， 生成 hydrobromide salt of (2S,3S,5R)-2-(3,5-difluorophenyl)-3,5-dimethyl-2-morpholinol
  参考文献：
  名称：

  （2S，3S，5R）-2-（3,5-二氟苯基）-3,5-二甲基-2-吗啉醇：一种新型的抗抑郁药和去甲肾上腺素摄取的选择性抑制剂。

  摘要：

  DOI：

  10.1021/jm950630p
• 作为产物：
  描述：

  3,5-二氟苯丙酮 在 溴 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到2-bromo-3',5'-difluoropropiophenone
  参考文献：
  名称：

  [EN] MONOAMINE REUPTAKE INHIBITORS
  [FR] INHIBITEURS DE LA RECAPTURE DES MONOAMINES

  摘要：

  该发明提供了一种能够抑制一种或多种单胺再摄取的丁丙吡胺类似化合物。这些化合物可以选择性地结合到一种或多种单胺转运体上，包括多巴胺、去甲肾上腺素和5-羟色胺的转运体。这些化合物可用于治疗对单胺再摄取抑制有响应的疾病，包括成瘾、抑郁和肥胖症。

  公开号：

  WO2010121022A1

文献信息

• Heterocyclic pharmaceutical compounds and use
  申请人：Burroughs Wellcome Co.

  公开号：US05104870A1

  公开（公告）日：1992-04-14

  Novel (2S, 3S, 5R) morpholinols of formula (I) ##STR1## together with the (+-)-(2R*,3R*,5S*) racemates thereof, and their salts, wherein X is hydrogen, alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 6 carbon atoms or a group --CH.sub.2 --X.sup.1 where X.sup.1 is cycloalkyl of 3 to 6 carbon atoms. The compounds have a variety of uses in human medicine, in particular in the treatment of mental disorders such as depression.

  小说（2S，3S，5R）形式（I）##STR1## 的吗啡啶醇，以及其（+-）-（2R*，3R*，5S*）外消旋体及其盐，其中X为氢，碳原子数为1至6的烷基，碳原子数为3至6的环烷基或基团--CH.sub.2--X.sup.1，其中X.sup.1为碳原子数为3至6的环烷基。这些化合物在人类医学中有各种用途，特别是在治疗抑郁等精神障碍方面。
• MONOAMINE REUPTAKE INHIBITORS
  申请人：Carroll Frank Ivy

  公开号：US20120071560A1

  公开（公告）日：2012-03-22

  The invention provides bupropion analogue compounds capable of inhibiting the reuptake of one or more monoamines. The compounds may selectively bind to one or more monoamine transporters, including those for dopamine, norepinephrine, and serotonin. Such compounds may be used to treat conditions that are responsive to inhibition of the reuptake of monoamines, including addiction, depression, and obesity.

  本发明提供了能够抑制一种或多种单胺再摄取的伯泊隆类似化合物。该化合物可以选择性地结合到一种或多种单胺转运体上，包括多巴胺、去甲肾上腺素和血清素。这种化合物可用于治疗对单胺再摄取抑制有反应的疾病，包括成瘾、抑郁和肥胖症。
• Monoamine reuptake inhibitors
  申请人：Research Triangle Institute

  公开号：US10919841B2

  公开（公告）日：2021-02-16

  The invention provides bupropion analogue compounds capable of inhibiting the reuptake of one or more monoamines. The compounds may selectively bind to one or more monoamine transporters, including those for dopamine, norepinephrine, and serotonin. Such compounds may be used to treat conditions that are responsive to inhibition of the reuptake of monoamines, including addiction, depression, and obesity.

  本发明提供了能够抑制一种或多种单胺再摄取的安非他酮类似物化合物。这些化合物可选择性地与一种或多种单胺转运体结合，包括多巴胺、去甲肾上腺素和血清素的转运体。此类化合物可用于治疗对抑制单胺再摄取有反应的病症，包括成瘾、抑郁症和肥胖症。
• Synthesis and Biological Evaluation of Bupropion Analogues as Potential Pharmacotherapies for Cocaine Addiction
  作者：F. Ivy Carroll、Bruce E. Blough、Philip Abraham、Andrew C. Mills、J. Ashley Holleman、Scott A. Wolckenhauer、Ann M. Decker、Antonio Landavazo、K. Timothy McElroy、Hernán A. Navarro、Michael B. Gatch、Michael J. Forster

  DOI：10.1021/jm901189z

  日期：2009.11.12

  A series of bupropion (1a) analogues (1b-1ff) were synthesized, and their in vitro and in vivo pharmacological properties evaluated with the goal of developing a la analogue that had better properties for treating addictions. Their in vitro pharmacological properties were examined by [H-3]dopamine ([H-3]DA), [H-3]serotonin ([H-3](HT)-H-5), and [H-3]norepinephrine ([H-3]NE) uptake inhibition studies, and by binding studies at the dopamine, serotonin, and norepinephrine transporters using [I-125]RTI-55 in cloned transporters. Several analogues showed increased [H-3]DA uptake inhibition with reduced or little change in [H-3](HT)-H-5 and [H-3]NE uptake inhibition relative to bupropion. Thirty-five analogues were evaluated in a 1 h locomotor activity observation test and 32 in an 8 h locomotor activity observation test and compared to the locomotor activity of cocaine. Twenty-four analogues were evaluated for generalization to cocaine drug discrimination after i.p. administration, and twelve analogues were tested in a tithe course cocaine discrimination study using oral administration. 2-(N-Cyclopropylamino)-3-chloropropiophenone (1x) had the most favorable in vitro efficacy and in vivo pharmacological profile for an indirect dopamine agonist pharmacotherapy for treating cocaine, methamphetamine, nicotine, and other drugs of abuse addiction.
• Novel morpholinol compounds, their preparation and use
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0426416B1

  公开（公告）日：1994-02-16