(2E)-4-[(2-氟苯基)氨基]-4-氧代-2-丁烯酸 | 63539-50-4

• 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: (2E)-4-[(2-氟苯基)氨基]-4-氧代-2-丁烯酸
• 英文名称: (2-flurophenyl)maleamic acid
• 英文别名: N-(2-Fluorphenyl)-maleamsaeure；(Z)-4-(2-fluoroanilino)-4-oxobut-2-enoic acid
• CAS: 63539-50-4
• 化学式: C₁₀H₈FNO₃
• 分子量: 209.177
• InChiKey: NVKBZXHSDUVZDI-WAYWQWQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2924299090

反应信息

• 作为反应物：
  描述：

  (2E)-4-[(2-氟苯基)氨基]-4-氧代-2-丁烯酸 在 硫酸 、 溶剂黄146 作用下， 反应 0.75h， 生成 1-(2-氟苯基)-1H-吡咯-2,5-二酮
  参考文献：
  名称：

  DABCO催化的偶氮甲亚胺与N-芳基马来酰亚胺的[3 + 2]环加成反应：易于接近二氮稠合的杂环

  摘要：

  已经开发了DABCO与马来酰亚胺偶氮甲亚胺的[3 + 2]环加成反应。该方法可以以高水平的区域选择性和良好的收率有效地提供二氮稠合的四环杂环。

  DOI：

  10.1016/j.tetlet.2015.11.030
• 作为产物：
  描述：

  马来酸酐 、 2-氟苯胺 以 乙醚 为溶剂， 生成 (2E)-4-[(2-氟苯基)氨基]-4-氧代-2-丁烯酸
  参考文献：
  名称：

  N-取代的马来酰亚胺衍生物作为选择性甘油单酯脂肪酶抑制剂的合成及体外评价

  摘要：

  内源性大麻素2-花生四烯酸甘油酯（2-AG）在许多生理过程中起着重要作用，其作用通过甘油单酯脂肪酶（MGL）催化的酶促水解迅速终止。调节其内源水平可以提供治疗机会；然而，到目前为止，几乎没有描述选择性的MGL抑制剂。在这里，我们描述了N-取代的马来酰亚胺的合成及其对重组人脂肪酸酰胺水解酶（FAAH）和纯化人MGL的药理评价。先前已经描述了一些N-芳基马来酰亚胺（萨里奥（SM）；萨洛（OM）；Nevalainen，T .；Poso，A。莱蒂宁（JT）；贾文恩（T. Jarvinen）Niemi，R.大鼠小脑膜中2-花生四烯酸甘油水解酶中巯基敏感位点的表征。化学 生物学 2005年，12，649-656），为MGL抑制剂，以及沿着这些线路，我们提出一组新的马来酰亚胺衍生物的那显示出低微摩尔的IC 50和朝向MGL VS FAAH高选择性。然后，研究了结构活性关系，例如，1-biphenyl-4

  DOI：

  10.1021/jm900461w

文献信息

• Inter-Ring Torsions in <i>N</i>-Phenylmaleimide and Its <i>o</i>-Halo Derivatives:  An Experimental and Computational Study
  作者：Christopher W. Miller、Charles E. Hoyle、Edward J. Valente、David H. Magers、E. Sonny Jönsson

  DOI：10.1021/jp9905474

  日期：1999.8.1

  Structures of N-phenylmaleimide and its o-halophenyl derivatives have been determined in the solid state and show the angle between the phenyl and pyrolinyl ring planes to vary from 49.5 degrees to 83.9 degrees with increasing values for compounds with the larger ortho halophenyl substituents (H < F less than or similar to Cl less than or similar to Br < I). Experimental torsions and trends in the series are supported by semiempirical AMI and ab initio SCF, DFT, and MP2 calculations. Calculations (AM1) on N-phenylmaleimide modeling the torsional deformation between the rings show that the barrier to planarity has a lower energy than that through a perpendicular conformation. In its o-halo derivatives, molecular planarity is not possible, and torsional deformation proceeds through the perpendicular conformation with diminishing, possibly vanishing, barriers with increasing halogen size. For chloro, bromo, and iodo derivatives, twisted ground-state molecular conformations reside in broad minima essentially centered around the perpendicular conformations. The unusually strong, longer wavelength electronic bands observed in the solution spectra of the series were modeled by Zindo/S CIS computations at the optimum AM1 molecular geometries. The observed lower energy (285-305 nm) band for the parent through the o-bromo derivative appears to arise from a n perpendicular to(O,N); pi (phenyl)} --> pi*(maleimide) transition. The next higher energy (250-285 nm) band appears to be essentially a phenyl pi --> pi* transition. In the o-iodo derivative, a phenyl pi --> sigma* (C-I) transition appears to contribute to the longer wavelength band. Trends in the observed electronic spectra in acetonitrile within the series of compounds accord roughly with the results of the computations.
• Curcumin-inspired cytotoxic 3,5-bis(arylmethylene)-1-(N-(ortho-substituted aryl)maleamoyl)-4-piperidones: A novel group of topoisomerase II alpha inhibitors
  作者：Amitabh Jha、Katherine M. Duffield、Matthew R. Ness、Sujatha Ravoori、Gabrielle Andrews、Khushwant S. Bhullar、H.P. Vasantha Rupasinghe、Jan Balzarini

  DOI：10.1016/j.bmc.2015.08.023

  日期：2015.10

  Three series of novel 3,5-bis(arylmethylene)-1-(N-(ortho-substituted aryl)maleamoyl)-4-piperidones, designed as simplified analogs of curcumin with maleic diamide tether, were synthesized and bioevaluated. These compounds displayed potent cytotoxicity towards human Molt 4/C8 and CEM T-lymphocytes as well as murine L1210 leukemic cells. In contrast, the related N-arylmaleamic acids possessed little or no cytotoxicity in these three screens. Design of these compounds was based on molecular modeling studies performed on a related series of molecule in a previous study. Representative title compounds were found to be significantly potent in inhibiting the activity of topoisomerase II alpha indicating the possible mode of action of these compounds. These compounds were also potent antioxidants in vitro and attenuated the AAPH triggered peroxyl radical production in human fibroblasts. Various members of these series were also well tolerated in both in vitro and in vivo toxicity analysis. (C) 2015 Elsevier Ltd. All rights reserved.
• SALTS OF PAROXETINE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：EP1091958A1

  公开（公告）日：2001-04-18
• DICARBONYL DERIVATIVES AND METHODS OF USE
  申请人：Abraxis BioScience, Inc.

  公开号：EP2125694A2

  公开（公告）日：2009-12-02
• US7799954B2
  申请人：——

  公开号：US7799954B2

  公开（公告）日：2010-09-21