2-溴-N-(2-硝基苯基)乙酰胺 | 5326-94-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-溴-N-(2-硝基苯基)乙酰胺
• 英文名称: 2-bromo-N-(2-nitrophenyl)acetamide
• CAS: 5326-94-3
• 化学式: C₈H₇BrN₂O₃
• mdl: MFCD02974406
• 分子量: 259.059
• InChiKey: MDQWPKGGEFPESZ-UHFFFAOYSA-N

物化性质

• 熔点：
  74 °C(Solv: ethanol (64-17-5))
• 沸点：
  431.1±30.0 °C(Predicted)
• 密度：
  1.755±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  14
• 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：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  2-溴-N-(2-硝基苯基)乙酰胺 在 sodium hydroxide 、 二氧化硫 、 水 作用下， 生成 N-acetyl-glycine-(2-nitro-anilide)
  参考文献：
  名称：

  Reichert; Baege, Pharmazie, 1949, vol. 4, p. 149

  摘要：

  DOI：
• 作为产物：
  描述：

  2-硝基苯胺 、 溴乙酰溴 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 生成 2-溴-N-(2-硝基苯基)乙酰胺
  参考文献：
  名称：

  吡唑-咪唑-三唑杂化物的简易合成、抗菌评价和分子对接研究

  摘要：

  摘要 一系列十八唑-咪唑-三唑杂化物(2-(4-((2-(取代-1H-吡唑-1-基)-4-苯基-1H-咪唑-1-基)甲基)-1H- 1,2,3-三唑-1-基)-N-(取代)苯基乙酰胺)(6a-6r)通过原位生成的2-叠氮基-N-取代乙酰胺和N-炔丙基化吡唑之间的点击反应合成咪唑衍生物依次由1-(1H-咪唑-2-基)-1H-吡唑和炔丙基溴区域选择性地获得。合成化合物 (6a-6r) 的结构通过各种光谱研究（1D 和 2D NMR、FT-IR、HRMS）得到证实，并评估了抗菌活性。化合物 6m 对黑曲霉表现出优异的效力（MIC 值为 0.0064 µmol/mL）；甚至优于参考药物氟康唑（MIC 值 0.0112 µmol/mL）。更多，

  DOI：

  10.1016/j.molstruc.2020.129216

文献信息

• Design, Synthesis and Biological Evaluation of a Library of Thiocarbazates and Their Activity as Cysteine Protease Inhibitors
  作者：Zhuqing Liu、Michael C. Myers、Parag P. Shah、Mary Pat Beavers、Phillip A. Benedetti、Scott L. Diamond、Amos B. Smith,III、Donna M. Huryn

  DOI：10.2174/138620710791054303

  日期：2010.5.1

  Recently, we identified a novel class of potent cathepsin L inhibitors, characterized by a thiocarbazate warhead. Given the potential of these compounds to inhibit other cysteine proteases, we designed and synthesized a library of thiocarbazates containing diversity elements at three positions. Biological characterization of this library for activity against a panel of proteases indicated a significant preference for members of the papain family of cysteine proteases over serine, metallo-, and certain classes of cysteine proteases, such as caspases. Several potent inhibitors of cathepsin L and S were identified. The SAR data were employed in docking studies in an effort to understand the structural elements required for cathepsin S inhibition. This study provides the basis for the design of highly potent and selective inhibitors of the papain family of cysteine proteases.

  最近，我们鉴定出一类新型高效组织蛋白酶L抑制剂，其特点是具有硫卡巴脒头部结构。鉴于这些化合物有可能抑制其他半胱氨酸蛋白酶，我们设计并合成了一系列硫卡巴脒类化合物，这些化合物在三个位点上含有多样性元素。该化合物的生物活性鉴定结果显示，它们对木瓜蛋白酶家族的半胱氨酸蛋白酶相较于丝氨酸、金属蛋白酶以及某些类别的半胱氨酸蛋白酶（如胱天蛋白酶）表现出显著的选择性。我们鉴定出了几个高效的组织蛋白酶L和S抑制剂。通过对接研究，我们利用SAR数据来理解实现组织蛋白酶S抑制所需的结构要素。这项研究为设计高度有效且选择性的木瓜蛋白酶家族半胱氨酸蛋白酶抑制剂奠定了基础。
• Synthesis and α-Glucosidase Inhibition Activity of 2-[3-(Benzoyl/4-bromobenzoyl)-4-hydroxy-1,1-dioxido-2H-benzo[e][1,2]thiazin-2-yl]-N-arylacetamides: An In Silico and Biochemical Approach
  作者：Furqan Ahmad Saddique、Sana Aslam、Matloob Ahmad、Usman Ali Ashfaq、Muhammad Muddassar、Sadia Sultan、Saman Taj、Muzammil Hussain、Dae Sung Lee、Magdi E. A. Zaki

  DOI：10.3390/molecules26103043

  日期：——

  Diabetes mellitus (DM) is a chronic disorder and has affected a large number of people worldwide. Insufficient insulin production causes an increase in blood glucose level that results in DM. To lower the blood glucose level, various drugs are employed that block the activity of the α-glucosidase enzyme, which is considered responsible for the breakdown of polysaccharides into monosaccharides leading to an increase in the intestinal blood glucose level. We have synthesized novel 2-(3-(benzoyl/4-bromobenzoyl)-4-hydroxy-1,1-dioxido-2H-benzo[e][1,2]thiazin-2-yl)-N-arylacetamides and have screened them for their in silico and in vitro α-glucosidase inhibition activity. The derivatives 11c, 12a, 12d, 12e, and 12g emerged as potent inhibitors of the α-glucosidase enzyme. These compounds exhibited good docking scores and excellent binding interactions with the selected residues (Asp203, Asp542, Asp327, His600, Arg526) during in silico screening. Similarly, these compounds also showed good in vitro α-glucosidase inhibitions with IC50 values of 30.65, 18.25, 20.76, 35.14, and 24.24 μM, respectively, which were better than the standard drug, acarbose (IC50 = 58.8 μM). Furthermore, a good agreement was observed between in silico and in vitro modes of study.

  糖尿病（DM）是一种慢性疾病，已经影响了全球大量人口。胰岛素产量不足导致血糖水平升高，从而引发糖尿病。为了降低血糖水平，使用了各种药物来阻断α-葡萄糖苷酶的活性，该酶被认为是将多糖分解为单糖，导致肠道血糖水平升高的原因。我们合成了新型的2-(3-(苯甲酰/对溴苯甲酰)-4-羟基-1,1-二氧化-2H-苯并[e][1,2]噻嗪-2-基)-N-芳基乙酰胺，并对它们进行了体外和体内α-葡萄糖苷酶抑制活性的筛选。衍生物11c、12a、12d、12e和12g显示出对α-葡萄糖苷酶的强效抑制作用。这些化合物在体外筛选过程中表现出良好的对接得分，并与所选残基（Asp203、Asp542、Asp327、His600、Arg526）展现出优秀的结合相互作用。同样，这些化合物在体内也表现出良好的α-葡萄糖苷酶抑制作用，其IC50值分别为30.65、18.25、20.76、35.14和24.24 μM，优于标准药物阿卡波糖（IC50 = 58.8 μM）。此外，在体内和体外研究模式之间观察到了良好的一致性。
• A Search for Dual Action HIV-1 Reverse Transcriptase, Bacterial RNA Polymerase Inhibitors
  作者：Agata Paneth、Tomasz Frączek、Agnieszka Grzegorczyk、Dominika Janowska、Anna Malm、Piotr Paneth

  DOI：10.3390/molecules22111808

  日期：——

  Using molecular modeling approach, potential antibacterial agents with triazole core were proposed. A moderate to weak level of antibacterial activity in most of the compounds have been observed, with best minimal inhibitory concentration (MIC) value of 0.003 mg/mL, as shown by the 15 against S. epidermidis. Studied compounds were also submitted to the antifungal assay. The best antifungal activity

  使用分子建模方法，提出了具有三唑核的潜在抗菌剂。已观察到大多数化合物具有中等至微弱的抗菌活性，最佳最小抑菌浓度 (MIC) 值为 0.003 mg/mL，如针对表皮葡萄球菌的 15 所示。所研究的化合物也进行了抗真菌试验。对 16 种检测到最佳抗真菌活性，MIC 分别为 0.125 和 0.25 mg/mL，分别对抗白色念珠菌和近平滑念珠菌。
• Synthesis, crystal structure and antimicrobial activity of 2-((2-(4-(1H-1,2,4-triazol-1-yl)phenyl)quinazolin-4-yl)oxy)-N-phenylacetamide derivatives against phytopathogens
  作者：Zhijiang Fan、Jun Shi、Na Luo、Xiaoping Bao

  DOI：10.1007/s11030-018-9896-2

  日期：2019.8

  total of eighteen 2-((2-(4-(1H-1,2,4-triazol-1-yl)phenyl)quinazolin-4-yl)oxy)-N-phenylacetamide derivatives were designed and synthesized, via hybrid pharmacophore approach. Among these compounds, chemical structure of compound 4a was unambiguously confirmed by means of single-crystal X-ray diffraction analysis. All the compounds were evaluated in vitro for their inhibition activity against several important

  摘要总共设计并合成了18种2-（（2-（4-（1 H -1,2,4-三唑-1-基）苯基）喹唑啉-4-基）氧基）-N-苯基乙酰胺衍生物杂交药效团方法。在这些化合物中，通过单晶X射线衍射分析明确地确认了化合物4a的化学结构。体外评估了所有化合物对农业中几种重要植物致病菌和真菌的抑制活性。获得的结果表明，几种化合物显示出对米黄单胞菌PV的有效抗菌活性。稻（Xoo）。例如，化合物4c，4g和4q对这种细菌的EC 50值分别为35.0、36.5和32.4 µg / mL，活性是商业杀菌剂比美噻唑（EC 50  = 89.8 µg / mL）的1.5倍左右。此外，化合物4J和4P被发现显示出针对可比的抗真菌活性的Gloeosporium苹果炭疽病在50微克/毫升，于商业杀菌剂恶霉灵。最后，详细讨论了这类化合物的抗菌活性与分子结构之间的关系。 图形概要
• 2-(Quinolin-4-yloxy)acetamides Are Active against Drug-Susceptible and Drug-Resistant <i>Mycobacterium tuberculosis</i> Strains
  作者：Kenia Pissinate、Anne Drumond Villela、Valnês Rodrigues-Junior、Bruno Couto Giacobbo、Estêvão Silveira Grams、Bruno Lopes Abbadi、Rogério Valim Trindade、Laura Roesler Nery、Carla Denise Bonan、Davi Fernando Back、Maria Martha Campos、Luiz Augusto Basso、Diógenes Santiago Santos、Pablo Machado

  DOI：10.1021/acsmedchemlett.5b00324

  日期：2016.3.10

  described as potent in vitro inhibitors of Mycobacterium tuberculosis growth. Herein, additional chemical modifications of lead compounds were carried out, yielding highly potent antitubercular agents with minimum inhibitory concentration (MIC) values as low as 0.05 muM. Further, the synthesized compounds were active against drug-resistant strains and were devoid of apparent toxicity to Vero and HaCat

  2-（喹啉-4-基氧基）乙酰胺已被描述为结核分枝杆菌生长的有效体外抑制剂。在此，对前导化合物进行了其他化学修饰，从而产生了具有最低抑菌浓度（MIC）值低至0.05μM的高效抗结核药。此外，合成的化合物对耐药菌株具有活性，并且对Vero和HaCat细胞没有明显的毒性（IC50> / = 20μM）。此外，2-（喹啉-4-基氧基）乙酰胺在感染的巨噬细胞中显示出针对细菌的细胞内活性，其作用类似于利福平，药物-药物相互作用的风险低，并且斑马鱼（斑马鱼）的心脏毒性没有迹象。 1和5毫米。因此，这些数据表明此类化合物可为将来的开发提供候选，