3-bromo-N-(2-chlorophenyl)propanamide | 26974-77-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-bromo-N-(2-chlorophenyl)propanamide
• CAS: 26974-77-6
• 化学式: C₉H₉BrClNO
• 分子量: 262.534
• InChiKey: RVIDDPVOLDPNMW-UHFFFAOYSA-N

物化性质

• 熔点：
  85-86 °C(Solv: benzene (71-43-2))
• 沸点：
  393.1±27.0 °C(Predicted)
• 密度：
  1.599±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-bromo-N-(2-chlorophenyl)propanamide 在 三氟甲磺酸 、 sodium t-butanolate 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 8-氯-2,3-二氢喹啉-4(1H)-酮
  参考文献：
  名称：

  Chroman and tetrahydroquinoline ureas as potent TRPV1 antagonists

  摘要：

  Novel chroman and tetrahydroquinoline ureas were synthesized and evaluated for their activity as TRPV1 antagonists. It was found that aryl substituents on the 7- or 8-position of both bicyclic scaffolds imparted the best in vitro potency at TRPV1. The most potent chroman ureas were assessed in chronic and acute pain models, and compounds with the ability to cross the blood-brain barrier were shown to be highly efficacious. The tetrahydroquinoline ureas were found to be potent CYP3A4 inhibitors, but replacement of bulky substituents at the nitrogen atom of the tetrahydroisoquinoline moiety with small groups such as methyl can minimize the inhibition. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.056
• 作为产物：
  描述：

  3-溴丙酰氯 、 邻氯苯胺 在 三乙胺 作用下， 以 苯 为溶剂， 反应 4.0h， 以60%的产率得到3-bromo-N-(2-chlorophenyl)propanamide
  参考文献：
  名称：

  [β-（芳酰基氨基）乙基]哌嗪和-哌啶和[2-[（（芳基氨基羰基）羰基]乙基]哌嗪，-吡嗪并吡啶并吲哚和-吡嗪并异喹啉的合成，生物学评估和定量构效关系分析。一类新的强效H1拮抗剂。

  摘要：

  已经合成了一些[β-（芳酰基氨基）乙基]哌嗪和-哌啶和[2-[（芳基氨基羰基]乙基]哌嗪，-哌啶，-吡嗪并吡啶并吲哚和-吡嗪并异喹啉，并在分离的豚鼠中研究了它们的H1-拮抗活性。回肠。定量的构效关系分析表明，这些化合物侧链的疏水性在其活性中起主要作用，而空间和电子因素则次要。所有这些化合物都作用于共同的受体，并似乎与该受体发生类似的相互作用。

  DOI：

  10.1021/jm00173a011

文献信息

• Chromanylurea compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor and uses thereof
  申请人：Gomtsyan Arthur

  公开号：US20060128689A1

  公开（公告）日：2006-06-15

  Compounds that are antagonists of the VR1 receptor, having formula (I) or a pharmaceutically acceptable salt, prodrug, or salt of a prodrug thereof, wherein A 1 , A 2 , A 3 , A 4 , R 7 , R 8 , R 9 , X, Y, Z, L, n, and m, are as defined herein, and are useful in disorders prevented or ameliorated by inhibiting the VR1 receptor.

  对VR1受体拮抗剂，其化学式为(I)或其药用可接受的盐、前药或前药的盐，其中A1、A2、A3、A4、R7、R8、R9、X、Y、Z、L、n和m的定义如本文所述，并且在通过抑制VR1受体预防或改善的疾病中具有用处。
• Synthesis, biological evaluation, and quantitative structure-activity relationship analysis of [.beta.-(aroylamino)ethyl]piperazines and -piperidines and [2-[(arylamino)carbonyl]ethyl]piperazines, -piperidines, -pyrazinopyridoindoles, and -pyrazinoisoquinolines. A new class of potent H1 antagonists
  作者：Mridula Saxena、Shiv K. Agarwal、G. K. Patnaik、Anil K. Saxena

  DOI：10.1021/jm00173a011

  日期：1990.11

  Some [beta-(Aroylamino)ethyl]piperazines and -piperidines and [2-[(Arylamino)carbonyl]ethyl]piperazines, -piperidines, -pyrazinopyridoindoles, and -pyrazinoisoquinolines have been synthesized and their H1-antagonistic activity studied in isolated guinea pig ileum. Quantitative structure-activity relationship analysis indicates that the hydrophobicity of the side chain of these compounds plays a major

  已经合成了一些[β-（芳酰基氨基）乙基]哌嗪和-哌啶和[2-[（芳基氨基羰基]乙基]哌嗪，-哌啶，-吡嗪并吡啶并吲哚和-吡嗪并异喹啉，并在分离的豚鼠中研究了它们的H1-拮抗活性。回肠。定量的构效关系分析表明，这些化合物侧链的疏水性在其活性中起主要作用，而空间和电子因素则次要。所有这些化合物都作用于共同的受体，并似乎与该受体发生类似的相互作用。
• Design, Synthesis and Biological Evaluation of Hydroxamic Acid Derivatives as Potential High Density Lipoprotein (HDL) Receptor CLA-1 Up-Regulating Agents
  作者：Xiaofang Chen、Li Wang、Yu Du、Yanbin Wu、Xiaojian Jia、Yuan Yang、Bin Hong

  DOI：10.3390/molecules16119178

  日期：——

  Trichostatin A (TSA) and suberoylanilide hydroxamic acid (SAHA) were reported in our recent publication as novel human high density lipoprotein (HDL) receptor CD36 and Lysosomal integral membrane protein-II Analogous-1 (CLA-1) up-regulators. As part of a broader effort to more fully explore the structure-activity relationships (SAR) of CLA-1 up-regulators, we synthesized a series of hydroxamic acid derivatives and evaluated their CLA-1 up-regulating activities in HepG2 cells. Some compounds exhibited over 10-fold up-regulation of CLA-1 expression in HepG2 cells at 10 μg/mL concentration. The compound 1g showed the best potency, with a lower EC50 than TSA (EC50 = 0.32 μM versus 1.2 μM). These compounds provide early new CLA-1 up-regulators with potential for treating atherosclerosis.

  在我们最近的出版物中报道，三氟氯乙酰胺（TSA）和水杨酰胺羟肟酸（SAHA）被发现是新型的人类高密度脂蛋白（HDL）受体CD36和溶酶体整合膜蛋白-II类似物1（CLA-1）的上调剂。作为更全面探索CLA-1上调剂结构-活性关系（SAR）的一部分，我们合成了一系列羟肟酸衍生物，并在HepG2细胞中评估了它们的CLA-1上调活性。某些化合物在10 μg/mL浓度下表现出超过10倍的CLA-1表达上调。化合物1g展现出最佳效力，其EC50低于TSA（EC50 = 0.32 μM对比1.2 μM）。这些化合物提供了早期的新CLA-1上调剂，具有治疗动脉粥样硬化的潜力。
• SAXENA, MRIDULA;AGARWAL, SHIV K.;PATNAIK, G. K.;SAXENA, ANIL K., J. MED. CHEM., 33,(1990) N1, C. 2970-2976
  作者：SAXENA, MRIDULA、AGARWAL, SHIV K.、PATNAIK, G. K.、SAXENA, ANIL K.

  DOI：——

  日期：——
• Chroman and tetrahydroquinoline ureas as potent TRPV1 antagonists
  作者：Robert G. Schmidt、Erol K. Bayburt、Steven P. Latshaw、John R. Koenig、Jerome F. Daanen、Heath A. McDonald、Bruce R. Bianchi、Chengmin Zhong、Shailen Joshi、Prisca Honore、Kennan C. Marsh、Chih-Hung Lee、Connie R. Faltynek、Arthur Gomtsyan

  DOI：10.1016/j.bmcl.2011.01.056

  日期：2011.3

  Novel chroman and tetrahydroquinoline ureas were synthesized and evaluated for their activity as TRPV1 antagonists. It was found that aryl substituents on the 7- or 8-position of both bicyclic scaffolds imparted the best in vitro potency at TRPV1. The most potent chroman ureas were assessed in chronic and acute pain models, and compounds with the ability to cross the blood-brain barrier were shown to be highly efficacious. The tetrahydroquinoline ureas were found to be potent CYP3A4 inhibitors, but replacement of bulky substituents at the nitrogen atom of the tetrahydroisoquinoline moiety with small groups such as methyl can minimize the inhibition. (C) 2011 Elsevier Ltd. All rights reserved.