2-bromo-N-(2,5-dichlorophenyl)acetamide | 349120-85-0

• 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: 2-bromo-N-(2,5-dichlorophenyl)acetamide
• CAS: 349120-85-0
• 化学式: C₈H₆BrCl₂NO
• mdl: MFCD02974352
• 分子量: 282.952
• InChiKey: XHGXJQWMLXFCSZ-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：
  0.125
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  2-bromo-N-(2,5-dichlorophenyl)acetamide 在 potassium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 N-(2,5-dichlorophenyl)-N-methyl-2-(methylamino)acetamide
  参考文献：
  名称：

  Synthesis, Screening, and Molecular Modeling of New Potent and Selective Antagonists at the α_1d Adrenergic Receptor

  摘要：

  In the present study, more than 75 compounds structurally related to BMY 7378 have been designed and synthesized. Structural variations of each part of the reference molecule have been introduced, obtaining highly selective ligands for the aid adrenergic receptor. The molecular determinants for selectivity at this receptor are essentially, held by the phenyl substituent in the phenylpiperazine moiety. The integration of an extensive SAR analysis with docking simulations using the rhodopsin-based models of the three alpha(1)-AR subtypes and of the 5-HT1A receptor provides significant insights into the characterization of the receptor binding sites as well as into the molecular determinants of ligand selectivity at the alpha(1d)-AR and the 5-HT1A receptors. The results of multiple copies simultaneous search (MCSS) on the substituted phenylpiperazines together with those of manual docking of compounds BAN 7378 and 69 into the putative binding sites of the alpha(1a)-AR, alpha(1b)-AR, alpha(1d)-AR, and the 5-HT1A receptors suggest that the phenylpiperazine moiety would dock into a site formed by amino acids in helices 3, 4, 5, 6 and extracellular loop 2, (E2), whereas the spirocyclic ring of the ligand docks into a site formed by amino acids of helices 1, 2, 3, and 7. This docking mode is consistent with the SAR data produced in this work. Furthermore, the binding site of the imide moiety does not allow for the simultaneous involvement of the two carbonyl oxygen atoms in H-bonding, interactions, consistent with the SAR data, in particular with the results obtained with the lactam derivative 128. The results of docking simulations also suggest that the second and third extracellular loops may act as selectivity filters for the substituted phenylpiperazines. The most potent and selective compounds for alpha(1d) adrenergic receptor, i.e., 69 (Rec 26D/038) and 128 (Rec 26D/073), are characterized by the presence of the 2,5-dichlorophenylpiperazine moiety.

  DOI：

  10.1021/jm030944+
• 作为产物：
  描述：

  2,5-二氯苯胺 、 溴乙酰溴 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 生成 2-bromo-N-(2,5-dichlorophenyl)acetamide
  参考文献：
  名称：

  作为潜在抗癌剂的新型 N1-烷基化 1H-吲唑-3-甲酰胺衍生物的简便合成：体外、ADMET 预测和 SAR 研究

  摘要：

  这项工作的重点是通过光谱方法合成和表征新的吲唑化合物，这些化合物分别在 C 3和 N1 原子上含有羧酰胺和乙酰氨基 N 取代部分，其中乙酰氨基部分被认为是不同生物活性（包括抗癌活性）所必需的接头。在此背景下，研究了所有这些化合物对 MDA-MB-231、A-549 和 MCF-7 癌细胞系的抗增殖活性及其对正常成纤维细胞系 (NIH-3T3) 的细胞毒性活性。结果表明，在苯环第四位带有吸电子基团的化合物SN-1.1、SN-2.1和SN 3.2对具有GI 50的MCF-7细胞系表现出最有效的活性。值分别为 2.34±0.036、3.21±0.033 和 4.93±0.038 µM。通过各种计算机筛选技术评估进一步合成的化合物，以更好地了解药物相似性特征。所有化合物都显示出最佳的物理化学特征，作为优良的先导分子。在毒性分析研究中，预测所有化合物都没有致突变性和细胞毒性。这项工作提供了一类新的更安全的具有抗癌潜力的吲唑分子。

  DOI：

  10.1016/j.molstruc.2022.133727

文献信息

• Synthesis and biological evaluations of sulfanyltriazoles as novel HIV-1 non-nucleoside reverse transcriptase inhibitors
  作者：Zhiwei Wang、Baogen Wu、Kelli L. Kuhen、Badry Bursulaya、Truc N. Nguyen、Deborah G. Nguyen、Yun He

  DOI：10.1016/j.bmcl.2006.05.096

  日期：2006.8

  A novel sulfanyltriazole was discovered as an HIV-1 non-nucleoside reverse transcriptase inhibitor via HTS using a cell-based assay. Chemical modifications and molecular modeling studies were carried out to establish its SAR and understand its interactions with the enzyme. These modifications led to the identification of sulfanyltriazoles with low nanomolar potency for inhibiting HIV-1 replication and promising activities against selected NNRTI resistant mutants. These novel and potent sulfanyltriazoles could serve as advanced leads for further optimization. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis, Screening, and Molecular Modeling of New Potent and Selective Antagonists at the α_1d Adrenergic Receptor
  作者：Amedeo Leonardi、Daniela Barlocco、Federica Montesano、Giorgio Cignarella、Gianni Motta、Rodolfo Testa、Elena Poggesi、Michele Seeber、Pier G. De Benedetti、Francesca Fanelli

  DOI：10.1021/jm030944+

  日期：2004.4.1

  In the present study, more than 75 compounds structurally related to BMY 7378 have been designed and synthesized. Structural variations of each part of the reference molecule have been introduced, obtaining highly selective ligands for the aid adrenergic receptor. The molecular determinants for selectivity at this receptor are essentially, held by the phenyl substituent in the phenylpiperazine moiety. The integration of an extensive SAR analysis with docking simulations using the rhodopsin-based models of the three alpha(1)-AR subtypes and of the 5-HT1A receptor provides significant insights into the characterization of the receptor binding sites as well as into the molecular determinants of ligand selectivity at the alpha(1d)-AR and the 5-HT1A receptors. The results of multiple copies simultaneous search (MCSS) on the substituted phenylpiperazines together with those of manual docking of compounds BAN 7378 and 69 into the putative binding sites of the alpha(1a)-AR, alpha(1b)-AR, alpha(1d)-AR, and the 5-HT1A receptors suggest that the phenylpiperazine moiety would dock into a site formed by amino acids in helices 3, 4, 5, 6 and extracellular loop 2, (E2), whereas the spirocyclic ring of the ligand docks into a site formed by amino acids of helices 1, 2, 3, and 7. This docking mode is consistent with the SAR data produced in this work. Furthermore, the binding site of the imide moiety does not allow for the simultaneous involvement of the two carbonyl oxygen atoms in H-bonding, interactions, consistent with the SAR data, in particular with the results obtained with the lactam derivative 128. The results of docking simulations also suggest that the second and third extracellular loops may act as selectivity filters for the substituted phenylpiperazines. The most potent and selective compounds for alpha(1d) adrenergic receptor, i.e., 69 (Rec 26D/038) and 128 (Rec 26D/073), are characterized by the presence of the 2,5-dichlorophenylpiperazine moiety.
• Facile synthesis of new N1-alkylated 1H-indazole-3-carboxamide derivatives as potential anticancer agents: In vitro, ADMET prediction, and SAR studies
  作者：Sachin Puri、Kapil Juvale

  DOI：10.1016/j.molstruc.2022.133727

  日期：2022.12

  This work is focused on the synthesis and characterization by spectroscopic methods of new indazole compounds containing carboxamide and acetamido N-substituted moieties on C3 and N1 atoms, respectively, where acetamido moiety has been considered a linker essential for different biological activities including anticancer activity. In this context, the antiproliferative activity of all these compounds

  这项工作的重点是通过光谱方法合成和表征新的吲唑化合物，这些化合物分别在 C 3和 N1 原子上含有羧酰胺和乙酰氨基 N 取代部分，其中乙酰氨基部分被认为是不同生物活性（包括抗癌活性）所必需的接头。在此背景下，研究了所有这些化合物对 MDA-MB-231、A-549 和 MCF-7 癌细胞系的抗增殖活性及其对正常成纤维细胞系 (NIH-3T3) 的细胞毒性活性。结果表明，在苯环第四位带有吸电子基团的化合物SN-1.1、SN-2.1和SN 3.2对具有GI 50的MCF-7细胞系表现出最有效的活性。值分别为 2.34±0.036、3.21±0.033 和 4.93±0.038 µM。通过各种计算机筛选技术评估进一步合成的化合物，以更好地了解药物相似性特征。所有化合物都显示出最佳的物理化学特征，作为优良的先导分子。在毒性分析研究中，预测所有化合物都没有致突变性和细胞毒性。这项工作提供了一类新的更安全的具有抗癌潜力的吲唑分子。