2-bromo-N-(2,4-dimethoxyphenyl)acetamide | 349120-93-0

• 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-(2,4-dimethoxyphenyl)acetamide
• CAS: 349120-93-0
• 化学式: C₁₀H₁₂BrNO₃
• mdl: MFCD02676798
• 分子量: 274.114
• InChiKey: QHEGXQQLPNQOBF-UHFFFAOYSA-N

物化性质

• 沸点：
  394.2±37.0 °C(Predicted)
• 密度：
  1.492±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-bromo-N-(2,4-dimethoxyphenyl)acetamide 在 盐酸 、 水 、 caesium carbonate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 乙腈 为溶剂， 生成 2-[4-(2-chlorophenyl)sulfonyl-1,4-diazepan-1-yl]-N-(2,4-dimethoxyphenyl)acetamide
  参考文献：
  名称：

  Solution-Phase Parallel Synthesis and SAR of Homopiperazinyl Analogs as Positive Allosteric Modulators of mGlu₄

  摘要：

  Using a functional high-throughput screening (HTS) and subsequent solution-phase parallel synthesis approach, we have discovered a novel series of positive allosteric modulators for mGlu(4), a G-protein coupled receptor. This series is comprised of a homopiperazine central core. The solution-phase parallel synthesis and SAP, of analogs derived from this series will be presented. This series of positive allosteric modulators of mGlu(4) provide critical research tools to further probe the mGlu(4)-mediated effects in Parkinson's disease.

  DOI：

  10.1021/co1000508
• 作为产物：
  描述：

  溴乙酰氯 、 2,4-二甲氧基苯胺 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 2-bromo-N-(2,4-dimethoxyphenyl)acetamide
  参考文献：
  名称：

  2-（喹啉-4-基氧基）乙酰胺对药物敏感性和耐药性结核分枝杆菌菌株具有活性。

  摘要：

  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，

  DOI：

  10.1021/acsmedchemlett.5b00324

文献信息

• SAR and identification of 2-(quinolin-4-yloxy)acetamides as Mycobacterium tuberculosis cytochrome bc₁ inhibitors
  作者：Narisa Phummarin、Helena I. Boshoff、Patricia S. Tsang、James Dalton、Siouxsie Wiles、Clifton E. Barry 3rd、Brent R. Copp

  DOI：10.1039/c6md00236f

  日期：——

  A previous phenotypic screen by GSK identified 2-(quinolin-4-yloxy)acetamides as potent growth inhibitors of Mycobacterium tuberculosis (Mtb). We report the results of a preliminary structure-activity relationship (SAR) study of the compound class which has yielded more potent inhibitors. An Mtb cytochrome bd oxidase deletion mutant (cydKO) was found to be hypersensitive to most members of the compound

  GSK先前进行的表型筛选确定了2-（quinolin-4-yloxy）乙酰胺是结核分枝杆菌（Mtb）的有效生长抑制剂。我们报告了化合物类别的初步结构-活性关系（SAR）研究的结果，该化合物产生了更有效的抑制剂。发现Mtb细胞色素bd氧化酶缺失突变体（cydKO）对化合物库的大多数成员高度敏感，而带有qcrB基因单核苷酸多态性的菌株，该基因编码甲萘醌细胞色素c氧化还原酶（bc1）复合物的亚基，对图书馆有抵抗力。这些结果表明，Mtb生长抑制剂的2-（quinolin-4-yloxy）乙酰胺类可以添加到越来越多的针对结核分枝杆菌bc1复合体的支架中。
• Crystal structure, quantum chemical insights, and molecular docking studies of <i>N</i>aryl-2-(<i>N</i>-_{disubstituted}) acetamide compounds: potential inhibitors for neurodegenerative enzymes
  作者：Lorena Camargo-Ayala、Mauricio Bedoya、Luis Prent-Peñaloza、Efraín Polo-Cuadrado、Edison Osorio、Iván Brito、Gerzon E. Delgado、Wendy González、Margarita Gutierrez

  DOI：10.1039/d3ra08649f

  日期：——

  calculations by the MMGBSA method. Interestingly, compounds 5b, 5c and 5d showed much better ΔGbind than the reference drug Zonisamide. Compound 5c is the best in the series, which indicates a potential selective affinity of our compounds against MAO-B, which could be a promising finding in the search for new drugs for Parkinson's disease treatment. The acetamide crystal exhibits moderate NLO properties suggesting

  在世界人口寿命日益延长的背景下，神经退行性疾病的增加和人们对神经退行性疾病的关注不断增加。因此，寻找新药仍然是药物化学的首要任务。我们在这里介绍了一系列具有乙酰胺核的化合物的合成。它们的结构是利用紫外-可见光、核磁共振、高分辨质谱和红外技术建立的。此外，我们报告了通过 X 射线衍射从化合物5a-5d获得的晶体结构。这些化合物被评估为一氧化酶的潜在抑制剂； A (MAO-A) 和 B (MAO-B)，以及胆碱酯酶；使用诱导拟合对接 (IFD) 方法进行计算机模拟研究，并通过 MMGBSA 方法计算结合自由能 (Δ G结合)。有趣的是，化合物5b 、 5c和5d显示出比参考药物唑尼沙胺更好的 Δ G结合。化合物5c是该系列中最好的，这表明我们的化合物对 MAO-B 具有潜在的选择性亲和力，这可能是寻找帕金森病治疗新药的一个有希望的发现。乙酰胺晶体表现出中等的非线性光学特性，表明它可以被认为是非线性光学器件应用的潜在候选者。
• Synthesis and Evaluation of Thiazolyl-1<i>H</i>-benzo[<i>d</i>]imidazole Inhibitors of<i>Mycobacterium tuberculosis</i>Inosine Monophosphate Dehydrogenase
  作者：Kenia Pissinate、Diana Carolina Rostirolla、Laura Miranda Pinheiro、Priyanka Suryadevara、Perumal Yogeeswari、Dharmarajan Sriram、Luiz Augusto Basso、Pablo Machado、Diógenes Santiago Santos

  DOI：10.5935/0103-5053.20150104

  日期：——

  Using an orthologue-based design approach, we synthesized and assayed a series of thiazolyl-1H-benzo[d]imidazole derivatives as inhibitors of Mycobacterium tuberculosis inosine 5'-monophosphate dehydrogenase (MtIMPDH). From these experiments, a benzo[d]imidazole compound was described to inhibit the enzyme in the low micromolar range (K-i IMP = 0.55 +/- 0.02 mu M), which places this compound among the most potent in vitro MtIMPDH inhibitors developed to date. In addition, steady-state kinetic measurements and docking simulations were employed to determine its inhibition and interaction modes. The results described herein may be useful for the design and development of novel alternative therapeutics for tuberculosis that target MtIMPDH, a predicted to be essential (for optimal in vitro bacillus growth), druggable and assayable molecular target.
• Solution-Phase Parallel Synthesis and SAR of Homopiperazinyl Analogs as Positive Allosteric Modulators of mGlu₄
  作者：Yiu-Yin Cheung、Rocio Zamorano、Anna L. Blobaum、C. David Weaver、P. Jeffrey Conn、Craig W. Lindsley、Colleen M. Niswender、Corey R. Hopkins

  DOI：10.1021/co1000508

  日期：2011.3.14

  Using a functional high-throughput screening (HTS) and subsequent solution-phase parallel synthesis approach, we have discovered a novel series of positive allosteric modulators for mGlu(4), a G-protein coupled receptor. This series is comprised of a homopiperazine central core. The solution-phase parallel synthesis and SAP, of analogs derived from this series will be presented. This series of positive allosteric modulators of mGlu(4) provide critical research tools to further probe the mGlu(4)-mediated effects in Parkinson's disease.
• 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，