N-(4-nitrobenzyl)bromoacetamide | 191403-41-5

• 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-(4-nitrobenzyl)bromoacetamide
• 英文别名: 2-bromo-N-(4-nitrobenzyl)acetamide；2-bromo-N-[(4-nitrophenyl)methyl]acetamide；2‐bromo‐N‐(4‐nitrobenzyl)acetamide
• CAS: 191403-41-5
• 化学式: C₉H₉BrN₂O₃
• 分子量: 273.086
• InChiKey: ZDAFVPUVOHPOKZ-UHFFFAOYSA-N

物化性质

• 沸点：
  485.2±35.0 °C(Predicted)
• 密度：
  1.609±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  15
• 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：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(4-nitrobenzyl)bromoacetamide 在 四丁基碘化铵 、 一水合肼 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N-[(4-aminophenyl)methyl]-2-{1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-2-yl}acetamide
  参考文献：
  名称：

  取代的四氢异喹啉作为食欲素 1 受体的选择性拮抗剂

  摘要：

  越来越多的证据表明食欲素 1 (OX 1 ) 受体参与奖赏过程，表明 OX 1拮抗作用可能对药物成瘾有治疗作用。在开发 OX 1选择性拮抗剂的计划中，我们设计并合成了一系列取代的四氢异喹啉，并确定了它们在 OX 1和 OX 2钙动员测定中的效力。构效关系 (SAR) 研究揭示了有限的空间耐受性和对 7 位电子缺陷的偏好。表明吡啶甲基基团对于乙酰胺位置的活性是最佳的。计算研究产生了药效团模型并证实了 SAR 结果。化合物72 显着减弱了大鼠对可卡因的位置偏好的发展。

  DOI：

  10.1021/jm400720h
• 作为产物：
  描述：

  4-硝基苄胺 、 溴乙酸 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(4-nitrobenzyl)bromoacetamide
  参考文献：
  名称：

  Structure−Activity Relationships in the Binding of Chemically Derivatized CD4 to gp120 from Human Immunodeficiency Virus

  摘要：

  The first step in HIV infection is the binding of the envelope glycoprotein gp120 to the host cell receptor CD4. An interfacial "Phe43 cavity" in gp120, adjacent to residue Phe43 of gp120-bound CD4, has been suggested as a potential target for therapeutic intervention. We designed a CD4 mutant (D1D2F43C) for site-specific coupling of compounds for screening against the cavity. Altogether, 81 cysteine-reactive compounds were designed, synthesized, and tested. Eight derivatives exceeded the affinity of native D1D2 for gp 120. Structure-activity relationships (SAR) for derivatized CD4 binding to gp 120 revealed significant plasticity of the Phe43 cavity and a narrow entrance. The primary contacts for compound recognition inside the cavity were found to be van der Waals interactions, whereas hydrophilic interactions were detected in the entrance. This first SAR on ligand binding to an interior cavity of gp 120 may provide a starting point for structure-based assembly of small molecules targeting gp120-CD4 interaction.

  DOI：

  10.1021/jm070564e

文献信息

• Importance of the chromophore orientation to the ligand-to-metal energy transfer in lanthanide complexes with pendant-arm fitted cyclen derivatives
  作者：Gaël Zucchi、Rosario Scopelliti、Jean-Claude G. Bünzli

  DOI：10.1039/b101312m

  日期：——

  Both the energy parameter (i.e. the gap between the ligand triplet state and the metal ion excited state) and the geometric parameter (i.e. the donor–acceptor distance and the orientation of the choromophore) have to be taken into account to explain the results obtained in terms of the efficiency of the L→Ln intra-molecular energy transfer. Furthermore, the correlative comparison between structural

  三种衍生自镧系元素大环配合物的固态结构比较研究 1,4,7,10-四氮杂环十二烷 带吊臂轴承 酰胺为了评估影响配位多面体的参数并评估几何因素在能量转移过程中的重要性，已经进行了配位小组。在所有研究的结构中，配位几何都是单峰扭转方形反棱镜，这种情况通常在类似化合物中观察到。高分辨率发光光谱的complex配合物与金属离子的四方对称性是一致的。对给出的晶体结构和先前报道的晶体结构的分析表明：（i）O 4和N 4平面的相对取向不是由坐标确定的。溶剂分子和（ii）它们之间的扭转角主要由悬臂的柔韧性决定。Sm（III），Eu（III）和Tb（III）的配合物的发光特性的解释可以通过固态和溶液中的结构参数（通过核磁共振波谱）。两者的能量参数（即在之间的间隙配体三重态和金属离子激发态）和几何参数（即供体-受体距离和发色团的取向）必须加以考虑，以解释从L→Ln内-效率的结果。分子能量转移。此外，结构和发光
• Synthesis and antimicrobial activity of piperazine containing substituted 1,2,3-triazoles with amide linkage
  作者：Priyanka Yadav、C. P. Kaushik、Ashwani Kumar

  DOI：10.1080/00397911.2022.2132868

  日期：2022.11.17

  Abstract A series of Piperazine containing substituted 1,2,3-triazoles with amide linkage have been designed and synthesized via click reaction between 1-aryl-4-(prop-2-yn-1-yl)piperazines and N-aralkyl-2-bromoacetamides. All synthesized triazoles were explicated by various spectral techniques like 1H NMR, 13C NMR, Fourier transform infrared and high-resolution mass spectrometry. The synthesized compounds

  摘要 通过1- aryl -4-(prop-2-yn-1-yl)piperazines 和N -aralkyl-2-溴乙酰胺。所有合成的三唑化合物都通过各种光谱技术进行了解释，如1 H NMR、13 C NMR、傅里叶变换红外和高分辨率质谱。筛选合成的化合物对不同菌株的体外抗菌活性，即。枯草芽孢杆菌,表皮葡萄球菌,大肠杆菌,铜绿假单胞菌,白色念珠菌, Aspergillus niger表现出中等到良好的活性，而化合物7u显示出明显的活性，最低抑制浓度为 0.0248 µmol/mL。还探索了有效化合物7r和7u的分子对接研究。还对合成的三唑进行了 ADME（吸收、分布、代谢和排泄）研究，以展望药物的类似特性。
• 10.1016/j.molstruc.2024.138882
  作者：Yadav, Jyoti、Kaushik

  DOI：10.1016/j.molstruc.2024.138882

  日期：——

  appended 1,2,3-triazole hybrids of biotic interest was synthesized using terminal alkynes containing quinoline moiety, benzyl amine based bromides, sodium azide via click chemistry protocol and were assessed for antimalarial and antimicrobial potential. All of the synthesized triazoles were characterized using different spectral techinques viz. FTIR, 1H NMR,13C NMR and HRMS. Antimalarial activity of the synthesized

  使用含有喹啉部分、苄胺基溴化物、叠氮化钠的末端炔烃合成了一个新的喹啉附加的 1,2,3-三唑杂交体库，并通过点击化学方案评估了抗疟和抗菌潜力。所有合成的三唑均使用不同的光谱技术，即 FTIR、1H NMR、13C NMR 和 HRMS 进行表征。合成的喹啉-三唑杂交种对恶性疟原虫菌株的抗疟活性显示出中等到良好的结果。合成的化合物还显示出对四种细菌（金黄色葡萄球菌、枯草芽孢杆菌、肺炎克雷伯菌、大肠杆菌）和两种真菌（白色念珠菌、黑曲霉）的良好抗菌潜力。还进行了分子对接研究和计算机模拟 ADME （吸收、分布、代谢和消除） 分析，以检查合成化合物的结合性和药物可能性。
• Structure−Activity Relationships in the Binding of Chemically Derivatized CD4 to gp120 from Human Immunodeficiency Virus
  作者：Hui Xie、Danny Ng、Sergey N. Savinov、Barna Dey、Peter D. Kwong、Richard Wyatt、Amos B. Smith、Wayne A. Hendrickson

  DOI：10.1021/jm070564e

  日期：2007.10.1

  The first step in HIV infection is the binding of the envelope glycoprotein gp120 to the host cell receptor CD4. An interfacial "Phe43 cavity" in gp120, adjacent to residue Phe43 of gp120-bound CD4, has been suggested as a potential target for therapeutic intervention. We designed a CD4 mutant (D1D2F43C) for site-specific coupling of compounds for screening against the cavity. Altogether, 81 cysteine-reactive compounds were designed, synthesized, and tested. Eight derivatives exceeded the affinity of native D1D2 for gp 120. Structure-activity relationships (SAR) for derivatized CD4 binding to gp 120 revealed significant plasticity of the Phe43 cavity and a narrow entrance. The primary contacts for compound recognition inside the cavity were found to be van der Waals interactions, whereas hydrophilic interactions were detected in the entrance. This first SAR on ligand binding to an interior cavity of gp 120 may provide a starting point for structure-based assembly of small molecules targeting gp120-CD4 interaction.
• Substituted Tetrahydroisoquinolines as Selective Antagonists for the Orexin 1 Receptor
  作者：David A. Perrey、Nadezhda A. German、Brian P. Gilmour、Jun-Xu Li、Danni L. Harris、Brian F. Thomas、Yanan Zhang

  DOI：10.1021/jm400720h

  日期：2013.9.12

  receptor in reward processes, suggesting OX1 antagonism could be therapeutic in drug addiction. In a program to develop an OX1 selective antagonist, we designed and synthesized a series of substituted tetrahydroisoquinolines and determined their potency in OX1 and OX2 calcium mobilization assays. Structure–activity relationship (SAR) studies revealed limited steric tolerance and a preference for electron

  越来越多的证据表明食欲素 1 (OX 1 ) 受体参与奖赏过程，表明 OX 1拮抗作用可能对药物成瘾有治疗作用。在开发 OX 1选择性拮抗剂的计划中，我们设计并合成了一系列取代的四氢异喹啉，并确定了它们在 OX 1和 OX 2钙动员测定中的效力。构效关系 (SAR) 研究揭示了有限的空间耐受性和对 7 位电子缺陷的偏好。表明吡啶甲基基团对于乙酰胺位置的活性是最佳的。计算研究产生了药效团模型并证实了 SAR 结果。化合物72 显着减弱了大鼠对可卡因的位置偏好的发展。