N-(3-chlorophenyl)-3-bromopropionamide | 77318-09-3

• 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: N-(3-chlorophenyl)-3-bromopropionamide
• 英文别名: 3-bromo-N-(3-chlorophenyl)propanamide
• CAS: 77318-09-3
• 化学式: C₉H₉BrClNO
• 分子量: 262.534
• InChiKey: ZMEPHROJAWAYOG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 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：

  N-(3-chlorophenyl)-3-bromopropionamide 在 一水合肼 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-(3-aminopropionyl)-3-chloroaniline
  参考文献：
  名称：

  Structure−Activity Relationships for the Binding of Arylpiperazines and Arylbiguanides at 5-HT₃ Serotonin Receptors

  摘要：

  Arylpiperazines are nonselective agents that bind at 5-HT3 serotonin receptors with moderate to high affinity, whereas 1-phenylbiguanide is a low-affinity but more selective 5-HT3 agonist. In an attempt to enhance the affinity of the latter agent, and working with the assumption that similarities might exist between the binding of the two types of agents, we formulated structure-activity relationships for the binding of the arylpiperazines and then incorporated those substituents, leading to high affinity for the arylpiperazines, into 1-phenylbiguanide. A subsequent investigation examined the structure-activity relationships of the arylbiguanides and identified arylguanidines as a novel class of 5-HT3 ligands. Although curious similarities exist between the structure-activity relationships of the arylpiperazines, arylbiguanides, and arylguanidines, it cannot be concluded that all three series of compounds are binding in the same manner. Furthermore, upon investigating pairs of compounds in the three series, the arylpiperazines behaved as 5-HT3 antagonists (von Bezold-Jarisch assay) whereas the arylbiguanides and arylguanidines acted as 5-HT3 agonists.

  DOI：

  10.1021/jm9603936
• 作为产物：
  描述：

  3-溴丙酰氯 、 3-氯苯胺 以 乙醚 为溶剂， 反应 2.0h， 以95%的产率得到N-(3-chlorophenyl)-3-bromopropionamide
  参考文献：
  名称：

  新型烷基哌嗪作为潜在多巴胺拮抗剂的合成与评价。

  摘要：

  在分离的兔耳动脉制剂中，几种烷基哌嗪（已知的三环抗精神病药的单环亚片段）被评估为多巴胺拮抗剂。制备和评估的化合物具有一般结构Ar-X-（CH2）nY，其中X = C，O和N，n = 1-3，Y大部分是4-甲基哌嗪。X-NH，n = 3，X =（Z）-CH-CH，n = 2，侧链上有一个吸电子基团的那些化合物，其多巴胺拮抗剂活性与氯氮平相当。结论是，在本研究中使用的受体制剂中，作为多巴胺拮抗剂的最佳活性，吩噻嗪样药物的整个三环结构（或至少大于一个单环系统）是必需的。

  DOI：

  10.1021/jm00138a007

文献信息

• Synthesis and evaluation of novel alkylpiperazines as potential dopamine antagonists
  作者：Richard A. Glennon、John J. Salley、Odd S. Steinsland、Sharon Nelson

  DOI：10.1021/jm00138a007

  日期：1981.6

  Several alkylpiperazines, monocyclic subfragments of known tricyclic neuroleptic agents, were evaluated as dopamine antagonists in the isolated rabbit ear artery preparation. Compound prepared and evaluated are of the general structure Ar-X-(CH2)n-Y, where X = C, O, and N, n = 1-3, and Y, for the most part, was 4-methylpiperazine. Those compounds where X - NH, n = 3, and X = (Z)-CH - CH, n = 2, with

  在分离的兔耳动脉制剂中，几种烷基哌嗪（已知的三环抗精神病药的单环亚片段）被评估为多巴胺拮抗剂。制备和评估的化合物具有一般结构Ar-X-（CH2）nY，其中X = C，O和N，n = 1-3，Y大部分是4-甲基哌嗪。X-NH，n = 3，X =（Z）-CH-CH，n = 2，侧链上有一个吸电子基团的那些化合物，其多巴胺拮抗剂活性与氯氮平相当。结论是，在本研究中使用的受体制剂中，作为多巴胺拮抗剂的最佳活性，吩噻嗪样药物的整个三环结构（或至少大于一个单环系统）是必需的。
• Metal binding pharmacophore click-derived discovery of new broad-spectrum metallo-β-lactamase inhibitors
  作者：Yu-Hang Yan、Hao-Sheng Ding、Kai-Rong Zhu、Bin-Song Mu、Yang Zheng、Meng-Yi Huang、Cong Zhou、Wen-Fang Li、Zhenling Wang、Yong Wu、Guo-Bo Li

  DOI：10.1016/j.ejmech.2023.115473

  日期：2023.9

  carbapenems. Currently, there is a lack of clinically useful MBL inhibitors, making it crucial to discover new inhibitor chemotypes that can potently target multiple clinically relevant MBLs. Herein we report a strategy that utilizes a metal binding pharmacophore (MBP) click approach to identify new broad-spectrum MBL inhibitors. Our initial investigation identified several MBPs including phthalic acid

  金属-β-内酰胺酶（MBL）的出现赋予了对几乎所有β-内酰胺抗生素（包括碳青霉烯类）的耐药性。目前，缺乏临床上有用的 MBL 抑制剂，因此发现能够有效靶向多种临床相关 MBL 的新抑制剂化学型至关重要。在此，我们报告了一种利用金属结合药效团 (MBP) 点击方法来识别新的广谱 MBL 抑制剂的策略。我们的初步研究确定了几种 MBP，包括邻苯二甲酸、苯基硼酸和苄基磷酸，它们使用叠氮-炔点击反应进行结构转变。随后的结构-活性关系分析导致了几种有效的广谱 MBL 抑制剂的鉴定，包括针对多种 MBL 的 IC 值范围为 0.00012 μM 至 0.64 μM。共晶研究证明了 MBP 在与 MBL 活性位点锚定药效团特征结合方面的重要性，并揭示了与 IMP-1 不寻常的两分子结合模式，强调了灵活的活性位点环在识别结构多样的底物/抑制剂中的关键作用。我们的工作为 MBL 抑制提供了新的化学型，并为针对
• GLENNON, R. A.;SALLEY, J. J. ,, JR;STEINSLAND, O. S.;NELSON, S., J. MED. CHEM., 1981, 24, N 6, 678-683
  作者：GLENNON, R. A.、SALLEY, J. J. ,, JR、STEINSLAND, O. S.、NELSON, S.

  DOI：——

  日期：——
• Structure−Activity Relationships for the Binding of Arylpiperazines and Arylbiguanides at 5-HT₃ Serotonin Receptors
  作者：Małgorzata Dukat、Ashraf A. Abdel-Rahman、Abd M. Ismaiel、Stacy Ingher、Milt Teitler、Laszlo Gyermek、Richard A. Glennon

  DOI：10.1021/jm9603936

  日期：1996.1.1

  Arylpiperazines are nonselective agents that bind at 5-HT3 serotonin receptors with moderate to high affinity, whereas 1-phenylbiguanide is a low-affinity but more selective 5-HT3 agonist. In an attempt to enhance the affinity of the latter agent, and working with the assumption that similarities might exist between the binding of the two types of agents, we formulated structure-activity relationships for the binding of the arylpiperazines and then incorporated those substituents, leading to high affinity for the arylpiperazines, into 1-phenylbiguanide. A subsequent investigation examined the structure-activity relationships of the arylbiguanides and identified arylguanidines as a novel class of 5-HT3 ligands. Although curious similarities exist between the structure-activity relationships of the arylpiperazines, arylbiguanides, and arylguanidines, it cannot be concluded that all three series of compounds are binding in the same manner. Furthermore, upon investigating pairs of compounds in the three series, the arylpiperazines behaved as 5-HT3 antagonists (von Bezold-Jarisch assay) whereas the arylbiguanides and arylguanidines acted as 5-HT3 agonists.