3-(4-bromophenyl)-pyrrolidine-2,5-dione | 1747-70-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3-(4-bromophenyl)-pyrrolidine-2,5-dione
• 英文别名: (+/-)-(4-Bromphenyl)-bernsteinsaeureimid；3-(4-Bromophenyl)pyrrolidine-2,5-dione
• CAS: 1747-70-2
• 化学式: C₁₀H₈BrNO₂
• 分子量: 254.083
• InChiKey: HKZFNZPZZPWZTM-UHFFFAOYSA-N

物化性质

• 沸点：
  427.1±45.0 °C(Predicted)
• 密度：
  1.606±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-(4-bromophenyl)-pyrrolidine-2,5-dione 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 48.0h， 生成 3-(4-bromophenyl)-1-(2-(2,4-difluorophenyl)-2-oxoethyl)-3-methylpyrrolidine-2,5-dione
  参考文献：
  名称：

  Identification and Profiling of Hydantoins—A Novel Class of Potent Antimycobacterial DprE1 Inhibitors

  摘要：

  Tuberculosis is the leading cause of death worldwide from infectious diseases. With the development of drug-resistant strains of Mycobacterium tuberculosis, there is an acute need for new medicines with novel modes of action. Herein, we report the discovery and profiling of a novel hydantoin-based family of antimycobacterial inhibitors of the decaprenylphospho-beta-D-ribofuranose 2-oxidase (DprE1). In this study, we have prepared a library of more than a 100 compounds and evaluated them for their biological and physicochemical properties. The series is characterized by high enzymatic and whole-cell activity, low cytotoxicity, and a good overall physicochemical profile. In addition, we show that the series acts via reversible inhibition of the DprE1 enzyme. Overall, the novel compound family forms an attractive base for progression to further stages of optimization and may provide a promising drug candidate in the future.

  DOI：

  10.1021/acs.jmedchem.8b01356
• 作为产物：
  描述：

  3-(4-bromophenyl)-5-(hydroxyimino)-4-(methylthio)-1H-pyrrol-2(5H)-one 在 盐酸 、 溶剂黄146 、 锌 作用下， 以 甲醇 、 水 为溶剂， 反应 122.5h， 生成 3-(4-bromophenyl)-pyrrolidine-2,5-dione
  参考文献：
  名称：

  Identification and Profiling of Hydantoins—A Novel Class of Potent Antimycobacterial DprE1 Inhibitors

  摘要：

  Tuberculosis is the leading cause of death worldwide from infectious diseases. With the development of drug-resistant strains of Mycobacterium tuberculosis, there is an acute need for new medicines with novel modes of action. Herein, we report the discovery and profiling of a novel hydantoin-based family of antimycobacterial inhibitors of the decaprenylphospho-beta-D-ribofuranose 2-oxidase (DprE1). In this study, we have prepared a library of more than a 100 compounds and evaluated them for their biological and physicochemical properties. The series is characterized by high enzymatic and whole-cell activity, low cytotoxicity, and a good overall physicochemical profile. In addition, we show that the series acts via reversible inhibition of the DprE1 enzyme. Overall, the novel compound family forms an attractive base for progression to further stages of optimization and may provide a promising drug candidate in the future.

  DOI：

  10.1021/acs.jmedchem.8b01356

文献信息

• Selective and tunable synthesis of 3-arylsuccinimides and 3-arylmaleimides from arenediazonium tetrafluoroborates and maleimides
  作者：Zhen-Hua Yang、Zhong-Hui Chen、Yu-Long An、Sheng-Yin Zhao

  DOI：10.1039/c6ra00136j

  日期：——

  arenediazonium tetrafluoroborates and maleimides in the presence of TiCl3. The reactions generated 3-arylsuccinimides in satisfactory yields under mild reaction conditions. In addition, 3-arylmaleimides were obtained by the coupling of arenediazonium tetrafluoroborate and maleimides catalyzed by CuCl. This methodology provided the selective and tunable synthesis of two classes of products by simply

  用于合成3- arylsuccinimides A高效合成策略已经从芳基重氮四氟硼酸盐和马来酰亚胺开发的TiCl的存在3。在温和的反应条件下，反应以令人满意的产率产生了3-芳基琥珀酰亚胺。另外，通过四氟硼酸壬二唑鎓与CuCl催化的马来酰亚胺的偶联，获得了3-芳基马来酰亚胺。通过简单地切换不同的金属试剂，该方法提供了两类产品的选择性和可调谐合成。该方法简单，高效，实用。
• Synthesis, 5-HT1A and 5-HT2A receptor affinity of new 1-phenylpiperazinylpropyl derivatives of purine-2,6- and pyrrolidine-2,5-diones
  作者：Maciej Pawłowski、Grażyna Chłoń、Jolanta Obniska、Alfred Zejc、Sijka Charakchieva-Minol、Maria J Mokrosz

  DOI：10.1016/s0014-827x(00)00069-0

  日期：2000.7

  Two series of 1-phenylpiperazinylpropyl derivatives 10, 11, 16, 17 and 19-24, structurally related to previously described 5-HT1A or 5-HT2A ligands 4 and 1, respectively, were synthesized and their binding properties were determined. Structural modifications which involved 1,3-diazepine ring opening in 4 (compounds 10, 11, 15, 16) and replacement of spiroalkyl moiety in 1 by aryl substituent (19-24) did not improve binding affinity and selectivity of the tested compounds. The results showed, however, that the diazepine ring present in 4 or spiroalkyl ring in 1 are important for high 5-HT1A or 5-HT2A binding affinity and selectivity of these compounds. (C) 2000 Elsevier Science S.A. All rights reserved.
• LANGE, JERZY;LAPSZEWICZ, JACEK;MIGAJ, BARBARA;SKRETA, KRYSTYNA, ACTA POL. PHARM., 44,(1987) N 3-4, 249-254
  作者：LANGE, JERZY、LAPSZEWICZ, JACEK、MIGAJ, BARBARA、SKRETA, KRYSTYNA

  DOI：——

  日期：——