2-bromo[methylhydrazono]acetic acid ethyl ester | 852816-29-6

• 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[methylhydrazono]acetic acid ethyl ester
• 英文别名: ethyl 2-bromo-2-(2-methylhydrazono)acetate；bromo[methylhydrazono] acetic acid ethyl ester；Ethyl 2-bromo-2-(methylhydrazinylidene)acetate；ethyl 2-bromo-2-(methylhydrazinylidene)acetate
• CAS: 852816-29-6
• 化学式: C₅H₉BrN₂O₂
• 分子量: 209.043
• InChiKey: ZCCFFMDLBMJGCH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  50.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-bromo[methylhydrazono]acetic acid ethyl ester 在 盐酸 、 水 、 乙酸乙酯 、 三乙胺 作用下， 生成 1-methyl-5-(4-tert-butylphenyl)-2H-pyrazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Development of a Scalable Synthesis of GSK183390A, a PPAR α/γ Agonist

  摘要：

  A scalable synthesis of GSK183390A, a PPAR alpha/gamma agonist, is described. This synthesis is highlighted by (1) a regioselective formal 1,3-dipolar cycloaddition reaction between an enamine and a nitrile imine dipole to form a 1,3,5-trisubstituted pyrazole and (2) a regioselective amidomethylation of an o-cresol derivative using 2-chloro-N-hydroxymethylacetamide.

  DOI：

  10.1021/op700164t
• 作为产物：
  描述：

  ethyl 2-(methylhydrazono)propanoate 在 N-溴代丁二酰亚胺(NBS) 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以95%的产率得到2-bromo[methylhydrazono]acetic acid ethyl ester
  参考文献：
  名称：

  [EN] SUBSTITUTED PYRAZOLES AS PPAR AGONISTS
  [FR] PYRAZOLES SUBSTITUES UTILISES EN TANT QU'AGONISTES DE PPAR

  摘要：

  式（I）的化合物及其药学上可接受的盐、溶剂化合物和可水解酯（I）其中：p为O或1；q为O或1；R1和R2独立地为H或C1-3烷基；R3和R4独立地为H、C1-6烷基、-OC1-6烷基、卤素、OH、C2-6烯基或CF3；R5为H、C1-6烷基（可选地被一个或多个卤素、-CO苯基、OC1-6烷基、苯基吗啡啉或C2-6烯基取代）。R6为C1-6烷基、卤素、-OCH2苯基、苯基（可选地被C1-3烷基取代）、吗啡啉、吡咯啉、哌啶、噻吩基、呋喃基吡啶基或-OC2-6烯基。这些化合物激活hppar受体的α和γ亚型，在糖尿病、血脂异常或X综合征的治疗中很有用。

  公开号：

  WO2005049578A1

文献信息

• Substituted <i>N</i>-Phenyl-5-(2-(phenylamino)thiazol-4-yl)isoxazole-3-carboxamides Are Valuable Antitubercular Candidates that Evade Innate Efflux Machinery
  作者：Elisa Azzali、Diana Machado、Amit Kaushik、Federica Vacondio、Sara Flisi、Clotilde Silvia Cabassi、Gyanu Lamichhane、Miguel Viveiros、Gabriele Costantino、Marco Pieroni

  DOI：10.1021/acs.jmedchem.7b00793

  日期：2017.8.24

  Tuberculosis remains one of the deadliest infectious diseases in the world, and the increased number of multidrug-resistant and extremely drug-resistant strains is a significant reason for concern. This makes the discovery of novel antitubercular agents a cogent priority. We have previously addressed this need by reporting a series of substituted 2-aminothiazoles capable to inhibit the growth of actively replicating, nonreplicating persistent, and resistant Mycobacterium tuberculosis strains. Clues from the structureactivity relationships lining up the antitubercular activity were exploited for the rational design of improved analogues. Two compounds, namely N-phenyl-5-(2-(p-tolylamino)thiazol-4-yl)isoxazole-3-carboxamide 7a and N-(pyridin-2-yl)-5-(2-(p-tolylamino)thiazol-4-yl)isoxazole-3-carboxamide 8a, were found to show high inhibitory activity toward susceptible M. tuberculosis strains, with an MIC90 of 0.1250.25 mu g/mL (0.330.66 mu M) and 0.060.125 mu g/mL (0.160.32 mu M), respectively. Moreover, they maintained good activity also toward resistant strains, and they were selective over other bacterial species and eukaryotic cells, metabolically stable, and apparently not susceptible to the action of efflux pumps.
• A new efficient synthesis of pyrazoles from hydrazonoyl halides and β-oxophosphonates
  作者：Aixue Sun、Jia-Hai Ye、Haitao Yu、Wenchao Zhang、Xiaolong Wang

  DOI：10.1016/j.tetlet.2013.12.045

  日期：2014.1

  A new practical and efficient synthesis of 1,3,5-trisubstituted pyrazoles has been developed by reacting of hydrazonoyl halides with beta-oxophosphonates under mild conditions in good yields with excellent regioselectivity. This process employs an addition-elimination sequence. Wide scope, functional group compatibility has been established. (C) 2013 Elsevier Ltd. All rights reserved.