2-bromo-N-(2-methoxyethyl)acetamide | 174215-37-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2-bromo-N-(2-methoxyethyl)acetamide
• 英文别名: N-(2-methoxyethyl)-bromoacetamide；2-methoxyethylbromoacetamide
• CAS: 174215-37-3
• 化学式: C₅H₁₀BrNO₂
• mdl: MFCD06800268
• 分子量: 196.044
• InChiKey: RLXVBFBDUXSRQW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S,3S)-3-hydroxy-2-(naphthalen-2-yl)-3-phenylpropyl(methyl)carbamate 、 2-bromo-N-(2-methoxyethyl)acetamide 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.67h， 以97%的产率得到
  参考文献：
  名称：

  [EN] INHIBITING NEUROTRANSMITTER REUPTAKE
  [FR] INHIBITION DU RECAPTAGE DE NEUROTRANSMETTEURS

  摘要：

  公开号：

  WO2014159251A3
• 作为产物：
  描述：

  溴乙酰溴 、 2-甲氧基乙胺 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以17%的产率得到2-bromo-N-(2-methoxyethyl)acetamide
  参考文献：
  名称：

  Biodegradable, non-bactericidal oxygen-functionalised imidazolium esters: A step towards ‘greener’ ionic liquids

  摘要：

  制备了一系列咪唑离子液体，并对7种细菌菌株进行了筛选。在酯侧链中引入醚基团与烷基酯衍生物相比显著降低了毒性。本文还提供了其中15种离子液体的生物降解数据，其中包括6个可归类为易生物降解的例子。

  DOI：

  10.1039/b812809j

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。
• Inhibition of Tumor Cell Growth by A Specific 6-Phosphofructo-2-kinase Inhibitor,<i>N</i>-Bromoacetylethanolamine Phosphate, and Its Analogues
  作者：Takafumi HIRATA、Mitsuaki WATANABE、Shinji MIURA、Katsushi IJICHI、Masashi FUKASAWA、Ryuzo SAKAKIBARA

  DOI：10.1271/bbb.64.2047

  日期：2000.1

  The high rate of glycolysis despite the presence of oxygen and mitochondria in tumor cells implies an important role for this process in cell division. The rate of glycolysis is assumed to be dependent on the cellular concentration of fructose 2,6-bisphosphate, the concentration of which in turn depends on a bifunctional enzyme and the ratio of this enzyme’s 6-phosphofructo-2-kinase versus its fructose 2,6-bisphosphatase activities. To prove the hypothesis that inhibition of glycolysis in tumor cells by 6-phosphofructo-2-kinase inhibitors would cause inhibition of tumor cell proliferation, ten N-bromoacetylethanolamine phosphate analogues were designed, synthesized, and tested. They were screened for their activities against various human tumor cell lines to study the effects of inhibition of glycolysis on cell proliferation. The relationship between the structure of these compounds and their inhibitory activity on cell proliferation was also discussed. It was found that the activity of N-(2-methoxyethyl)-bromoacetamide, N-(2-ethoxyethyl)-bromoacetamide, and N-(3-methoxypropyl)-bromoacetamide was comparable to that of the positive control AraC. These three inhibitors showed in vivo anticancer effects in P388 transplant BDF1 mice.

  尽管肿瘤细胞中存在氧和线粒体，但其糖酵解速率依然很高，这意味着该过程在细胞分裂中发挥着重要作用。糖酵解速率被认为依赖于细胞内果糖2,6-二磷酸的浓度，而果糖2,6-二磷酸的浓度又取决于一种双功能酶及该酶的6-磷酸果糖激酶与果糖2,6-二磷酸酶活性的比率。为了验证通过6-磷酸果糖激酶抑制剂抑制肿瘤细胞糖酵解将导致肿瘤细胞增殖抑制的假设，设计、合成并测试了十种N-溴乙酰乙醇胺磷酸类似物。对这些化合物在各种人类肿瘤细胞系中的活性进行了筛选，以研究抑制糖酵解对细胞增殖的影响。同时也讨论了这些化合物的结构与它们对细胞增殖抑制活性之间的关系。研究发现，N-(2-甲氧基乙基)-溴乙酰酰胺、N-(2-乙氧基乙基)-溴乙酰酰胺和N-(3-甲氧基丙基)-溴乙酰酰胺的活性与阳性对照AraC相当。这三种抑制剂在P388移植BDF1小鼠中显示了体内抗癌效果。
• Porphyrin catalysts and methods of use thereof
  申请人：Groves John T.

  公开号：US20100093688A1

  公开（公告）日：2010-04-15

  This invention provides a novel class of substituted macrocyclic porphyrin compounds. The compounds are useful as peroxynitrite decomposition catalysts. Pharmaceutical compositions, and methods of making and using the compounds, or a pharmaceutically acceptable salt, hydrate, or prodrug thereof are also described.

  这项发明提供了一类新型的取代的大环卟啉化合物。这些化合物可用作过氧亚硝酸盐分解催化剂。还描述了制备和使用这些化合物或其药用可接受的盐、水合物或前药的制药组合物和方法。
• Porphyrin Catalysts and Methods of Use Thereof
  申请人：Groves John T.

  公开号：US20120283236A1

  公开（公告）日：2012-11-08

  This invention provides a novel class of substituted macrocyclic porphyrin compounds. The compounds are useful as peroxynitrite decomposition catalysts. Pharmaceutical compositions, and methods of making and using the compounds, or a pharmaceutically acceptable salt, hydrate, or prodrug thereof are also described.

  该发明提供了一种新的取代的大环卟啉化合物类。这些化合物可用作过氧亚硝酸盐分解催化剂。还描述了制备和使用这些化合物或其药学上可接受的盐、水合物或前药的制药组合物和方法。
• Structure−Activity Relationships of 9-Substituted-9-Dihydroerythromycin-Based Motilin Agonists: Optimizing for Potency and Safety
  作者：Simon J. Shaw、Yue Chen、Hao Zheng、Hong Fu、Mark A. Burlingame、Saul Marquez、Yong Li、Mark Claypool、Christopher W. Carreras、William Crumb、Dwight J. Hardy、David C. Myles、Yaoquan Liu

  DOI：10.1021/jm901107f

  日期：2009.11.12

  A series of 9-dihydro-9-acetamido-N-desmethyl-N-isopropyl erythromycin A analogues and related derivatives was generated as motilin agonists. The compounds were optimized for potency while showing both minimal antibacterial activity and hERG inhibition. As the substituent on the amide was increased in lipophilicity the potency and hERG inhibition increased, while polar groups lowered potency, without significantly impacting hERG inhibition. The N-methyl acetamide 7a showed the optimal in vitro profile and was probed further by varying the chain length to the macrocycle as well as changing the macrocycle scaffold. 7a remained the compound with the best in vitro properties.