2-(3-chlorobenzoyl)-N,N-dimethylethylamine | 51949-06-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(3-chlorobenzoyl)-N,N-dimethylethylamine
• 英文别名: 1-(3-chlorophenyl)-3-(dimethylamino)propan-1-one；3-dimethylamino-1-(3-chlorophenyl)-propanone；1-(3-Chloro-phenyl)-3-dimethylamino-propan-1-one
• CAS: 51949-06-5
• 化学式: C₁₁H₁₄ClNO
• 分子量: 211.691
• InChiKey: STLLBHMDTDPHTM-UHFFFAOYSA-N

物化性质

• 熔点：
  193-195 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  310.0±27.0 °C(Predicted)
• 密度：
  1.115±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(3-chlorobenzoyl)-N,N-dimethylethylamine 在 正丁基锂 、 硫酸 、 溶剂黄146 作用下， 反应 3.25h， 生成 (E)-3-(3-chlorophenyl)-N,N-dimethyl-3-(3-pyridyl)allylamine
  参考文献：
  名称：

  与齐美啶有关的吡啶基烯丙基胺的合成及其对神经元单胺摄取的抑制作用。

  摘要：

  抗抑郁药齐美碱[6，（Z）-3-（4-溴苯基）-N，N-二甲基-3-（3-吡啶基）烯丙胺]的类似物是神经元5-羟色胺再摄取的选择性抑制剂，其合成方法如下：为了获得具有顺式构型（相对于吡啶基和烯丙胺）的化合物的几种途径。两种方法利用适当取代的苯甲酰基吡啶作为起始原料。在另外两个途径中，将6中的溴直接置换（CN）或通过相应的硫代衍生物转化为H，Cl，I，Me，SiMe3和SMe。通过UV，1H NMR和镧系元素引起的1H NMR位移确定构型。通过测量小鼠脑切片（体外和体内）中的[3H]去甲肾上腺素和5-羟基[14C]色胺的积累，将这些化合物评估为摄取抑制剂。在顺式系列中，对位取代有利于5-羟基色胺活性，而邻位取代有利于NA活性。对5-羟色胺的体外作用对对位取代基的变化不敏感，而仅用Cl，Br（6）和I观察到明显的体内作用。

  DOI：

  10.1021/jm00144a025
• 作为产物：
  描述：

  n,n-二甲基亚甲基碘化胺 、 3-氯苯乙酮 以 乙腈 为溶剂， 生成 2-(3-chlorobenzoyl)-N,N-dimethylethylamine
  参考文献：
  名称：

  Scaffold oriented synthesis. Part 2: Design, synthesis and biological evaluation of pyrimido-diazepines as receptor tyrosine kinase inhibitors

  摘要：

  We report the discovery of the pyrimido-diazepine scaffolds as novel adenine mimics. Structure-based design led to the discovery of analogs with potent inhibitory activity against receptor tyrosine kinases, such as KDR, Flt3 and c-Kit. Compound 14 exhibited low nanomolar KDR enzymatic and cellular potencies (IC50 = 9 and 52 nM, respectively). (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.03.021

文献信息

• PYRIDO PYRIMIDINES
  申请人：Anderson Kevin

  公开号：US20120184542A1

  公开（公告）日：2012-07-19

  Compounds of formula and pharmaceutically acceptable salts thereof are described, as well as the pharmaceutical compositions containing said compounds and their pharmaceutically acceptable salts, and the use of said compounds and pharmaceutical compositions for the treatment, control or amelioration of proliferative diseases, including cancer, Down syndrome or early onset Alzheimer's disease.

  具有该公式的化合物以及它们的药用可接受盐被描述，以及包含所述化合物及其药用可接受盐的药物组合物，以及所述化合物和药物组合物用于治疗、控制或改善增生性疾病，包括癌症、唐氏综合症或早发性阿尔茨海默病的使用。
• [EN] UROTENSIN II RECEPTOR MODULATORS<br/>[FR] MODULATEURS DU RECEPTEUR DE L'UROTENSINE II
  申请人：ACADIA PHARM INC

  公开号：WO2003104216A1

  公开（公告）日：2003-12-18

  Disclosed are compounds of Formula I, or salts or prodrugs thereof, complexed with a human urotensin II receptor as defined herein. Also disclosed are compounds of Formula II, or salts or prodrugs thereof, as defined herein. Also disclosed are methods of modulating the activity of a urotensin II receptor using a compound of Formula I, or a compound of Formula II, or salts or prodrugs thereof. In addition, methods of treating diseases related to the activity of urotensin II receptors are disclosed.

  本文披露了根据本文所定义的与人类尿嘧啶 II 受体形成络合物的 Formula I 化合物，或其盐或前药。还披露了根据本文所定义的 Formula II 化合物，或其盐或前药。还披露了使用 Formula I 化合物、Formula II 化合物、或其盐或前药来调节尿嘧啶 II 受体活性的方法。此外，还披露了治疗与尿嘧啶 II 受体活性相关疾病的方法。
• [EN] PYRIDINE DERIVATIVES AND ANTI-MYCOBACTERIAL USE THEREOF<br/>[FR] DÉRIVÉS DE PYRIDINE ET LEUR UTILISATION ANTI-MYCOBACTÉRIENNE<br/>[ZH] 吡啶衍生物及其作为抗分支杆菌的应用
  申请人：CISEN PHARMACEUTICAL CO LTD

  公开号：WO2016008381A1

  公开（公告）日：2016-01-21

  本发明公开了一系列新颖的吡啶衍生物的制备方法和应用。此类衍生物可用于治疗由分支杆菌引起的相关疾病，尤其是针对由致病性分支杆菌引起的疾病，如结核分枝杆菌，牛分支杆菌，鸟分支杆菌，及海分支杆菌。
• 6-Cyano Analogues of Bedaquiline as Less Lipophilic and Potentially Safer Diarylquinolines for Tuberculosis
  作者：Amy S. T. Tong、Peter J. Choi、Adrian Blaser、Hamish S. Sutherland、Sophia K. Y. Tsang、Jerome Guillemont、Magali Motte、Christopher B. Cooper、Koen Andries、Walter Van den Broeck、Scott G. Franzblau、Anna M. Upton、William A. Denny、Brian D. Palmer、Daniel Conole

  DOI：10.1021/acsmedchemlett.7b00196

  日期：2017.10.12

  Bedaquiline (1) is a new drug for tuberculosis and the first of the diarylquinoline class. It demonstrates excellent efficacy against TB but induces phospholipidosis at high doses, has a long terminal elimination half-life (due to its high lipophilicity), and exhibits potent hERG channel inhibition, resulting in clinical QTc interval prolongation. A number of structural ring A analogues of bedaquiline have been prepared and evaluated for their anti-M.tb activity (MIC90), with a view to their possible application as less lipophilic second generation compounds. It was previously observed that a range of 6 -substituted analogues of 1 demonstrated a positive correlation between potency (MIC90) toward M.tb and drug lipophilicity. Contrary to this trend, we discovered, by virtue of a clogP/M.tb score, that a 6-cyano (CN) substituent provides a substantial reduction in lipophilicity with only modest effects on MIC values, suggesting this substituent as a useful tool in the search for effective and safer analogues of 1.
• Synthesis and pharmacological evaluation of 3-aryl-3-azolylpropan-1-amines as selective triple serotonin/norepinephrine/dopamine reuptake inhibitors
  作者：Ki-Ho Lee、Chun-Eung Park、Kyung-Hyun Min、Yong-Je Shin、Coo-Min Chung、Hui-Ho Kim、Hae-Jeoung Yoon、Won-Kim、Eun-Ju Ryu、Yu-Jin Shin、Hyun-Sik Nam、Jeong-Woo Cho、Hee-Yoon Lee

  DOI：10.1016/j.bmcl.2010.07.021

  日期：2010.9

  A series of 3-aryl-3-azolylpropan-1-amines was prepared and screened for its capability of inhibiting monoamine reuptake. Analogs with nanomolar potency, good human in vitro microsomal stability, and low drug-drug interaction potential were described. In vivo models were used to evaluate the compound 19r for antidepressive, anxiolytic, and analgesic activity. (C) 2010 Elsevier Ltd. All rights reserved.