2-(N-isopropylamino)-3'-chloropropiophenone | 130839-36-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(N-isopropylamino)-3'-chloropropiophenone
• 英文别名: 2-(N-Isopropylamino)-3''-chloropropiophenone；1-(3-chlorophenyl)-2-(propan-2-ylamino)propan-1-one
• CAS: 130839-36-0
• 化学式: C₁₂H₁₆ClNO
• 分子量: 225.718
• InChiKey: WHPARCHZPIKXEX-UHFFFAOYSA-N

物化性质

• 沸点：
  325.3±27.0 °C(Predicted)
• 密度：
  1.082±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(N-isopropylamino)-3'-chloropropiophenone 在 盐酸 作用下， 以 乙醚 为溶剂， 以32%的产率得到1-(3-chlorophenyl)-2-(isopropylamino)propan-1-one hydrochloride
  参考文献：
  名称：

  安非他酮的解构类似物揭示了转运蛋白抑制与底物诱导的神经递质释放的结构要求。

  摘要：

  安非他酮（1）是多巴胺（DAT）和去甲肾上腺素（NET）在质膜转运蛋白上的α-氨基苯酮摄取抑制剂，是广泛使用的抗抑郁药和戒烟辅助剂。Cathinone（2）是结构简单的α-氨基苯酮，是在相同转运蛋白上的底物型脱模剂，并且是公认的滥用药物。我们的目标是确定控制从吸收抑制到底物诱导释放的机械转变的α-氨基苯甲酮的结构特征。合成了1的解构类似物，并使用体外分析方法比较了它们与DAT，NET和5-羟色胺转运蛋白（SERT）相互作用的能力。大量的胺取代基产生的化合物起DAT吸收抑制剂的作用，但不具有脱模剂的作用，而较小的胺取代基会在DAT和NET处产生相对非选择性的脱模剂。我们的发现增加了经验证据，这些证据支持与转运蛋白抑制剂相对的α-氨基苯甲酮（即，卡西酮-）相关药物具有不同的分子决定因素。

  DOI：

  10.1021/acschemneuro.7b00055
• 作为产物：
  描述：

  3-氯苯腈 在 溴 作用下， 以 乙醇 为溶剂， 生成 2-(N-isopropylamino)-3'-chloropropiophenone
  参考文献：
  名称：

  Synthesis and evaluation of the anticonvulsant activity of a series of 2-amino-1-phenyl-1-propanols derived from the metabolites of the antidepressant bupropion

  摘要：

  A series of 2-amino-1-phenyl-1-propanols that are structurally related to known metabolites of bupropion,1 (Wellbutrin(R)) were synthesized and evaluated as potential anticonvulsants. The (R*,R*)-2-tert-butylamino-1-(3-trifluoromethylphenyl) propanol 20 had an ED(50) of 16.5 +/- 2.8 mg/kg ip in mice in the maximal electroshock screen and was chosen for further evaluation. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00577-x

文献信息

• [EN] MONOAMINE REUPTAKE INHIBITORS<br/>[FR] INHIBITEURS DE LA RECAPTURE DES MONOAMINES
  申请人：RES TRIANGLE INST

  公开号：WO2010121022A1

  公开（公告）日：2010-10-21

  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.

  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。
• 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.
• US9562001B2
  申请人：——

  公开号：US9562001B2

  公开（公告）日：2017-02-07