2,3-dichloro-N-(p-nitrophenyl)maleimide | 29236-11-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯啉
• 英文名称: 2,3-dichloro-N-(p-nitrophenyl)maleimide
• 英文别名: N-4-nitrophenyldichloromaleimide；3,4-dichloro-1-(4-nitrophenyl)pyrrole-2,5-dione
• CAS: 29236-11-1
• 化学式: C₁₀H₄Cl₂N₂O₄
• 分子量: 287.059
• InChiKey: SPLZVLAXCUUTFU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,3-dichloro-N-(p-nitrophenyl)maleimide 在 硫脲 作用下， 以 乙腈 为溶剂， 以80%的产率得到
  参考文献：
  名称：

  Gǎinǎ, Constantin, Revue Roumaine de Chimie, 2005, vol. 50, # 7-8, p. 601 - 607

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(4-硝基苯基)马来酰亚胺 在 吡啶 、 氯化亚砜 作用下， 以87%的产率得到2,3-dichloro-N-(p-nitrophenyl)maleimide
  参考文献：
  名称：

  Gǎinǎ, Constantin, Revue Roumaine de Chimie, 2005, vol. 50, # 7-8, p. 601 - 607

  摘要：

  DOI：

文献信息

• Synthesis and Biological Evaluation of 3-Chloro-4-(indol-3-yl)-2,5- pyrroledione Derivatives as Antitumor Agents
  作者：Yuchen Lin、Jing Chen

  DOI：10.2174/1570180811310050003

  日期：2013.4.1

  A series of 3-chloro-4-(indol-3-yl)-2,5-pyrroledione derivatives were synthesized and evaluated for their cytotoxic activities in vitro against five human cancer cell lines (K562, A549, ECA-109, KB and SMMC-7721). Most compounds displayed potent cytotoxicity with IC50 values in low micromolar range. The results showed that the existence of the chlorine atom at 3-position on the pyrroledione ring was crucial for the activity. Compound 6a, the most potent one (IC50: 0.67∼3.93 μM), would be a promising template for further development of novel antitumor agents

  合成了一系列3-氯-4-(吲哚-3-基)-2,5-吡咯二酮衍生物，并评估其对五种人癌细胞系（K562、A549、ECA-109、KB和SMMC-7721）的体外细胞毒性活性。大多数化合物表现出强效的细胞毒性，IC50值在低微摩尔范围内。结果表明，吡咯二酮环上3位的氯原子的存在对活性至关重要。化合物6a是最有效的（IC50：0.67∼3.93 μM），将成为进一步开发新型抗肿瘤药物的有前景的模板。
• Synthesis of Novel 1,4-Benzoxazine-2,3-Dicarboximides from Maleic Anhydride and Substituted Aromatic Amines
  作者：Peng Wu、Yongzhou Hu

  DOI：10.1080/00397910802369638

  日期：2008.12.16

  Abstract A series of novel 1,4-benzoxazine-2,3-dicarboximides starting from maleic anhydride and substituted aromatic amines were synthesized.

  摘要 以马来酸酐和取代芳香胺为原料合成了一系列新型1,4-苯并恶嗪-2,3-二甲酰亚胺。
• Syntheses and structures of N-phenylmaleimidetriazoles and by-products
  作者：Yingqun Mao、Iain Maley、William H. Watson

  DOI：10.1007/s10870-005-1693-y

  日期：2005.5

  The syntheses, properties, and structures of N-phenylmaleimidetriazole derivatives are described. Intermediates and by-products are also discussed. 1b. a = 43.997(7) Å, 5.7610(9) Å, 8.245(1) Å, β = 99.339(4)∘, C2/c; 2a. a = 13.646(4) Å, b = 7.744(2) Å, c = 10.612(3) Å, β = 91.979(6)∘, P21/c. 3a. a = 22.245(1) Å, b = 22.245(1) Å, 10.010(1) Å, P42/n. 3a′. a = 11.727(2) Å, b = 14.075(3) Å, c = 16.080(3) Å, α = 105.859(3)∘, β = 105.331(3)∘, γ = 98.187(3)∘, P-1. 3b. a = 8.561(3) Å, b = 14.755(5) Å, c = 22.771(7) Å, β = 97.006(5)∘, P21/c. 3c. a = 10.500(2) Å, b = 12.189(2) Å, c = 13.040(2) Å, α = 109.091(3)∘, β = 106.089(3)∘, γ = 101.022(3)∘, P-1. 8a. a = 16.389(8) Å, b = 5.749(3) Å, c = 19.316(3) Å, β = 97.467(9)∘, P21/n. 8b. a = 5.822(2) Å, b = 10.114(3) Å, c = 16.705(4) Å, α = 84.681(5)∘, β = 82.840(5)∘, γ = 75.769(4)∘, P-1. 9b. a = 11.251(1) Å, 13.335(3) Å, 13.376(3) Å, β = 102.456(4)∘, P21/n. 9c. a = 15.836(3) Å, b = 8.236(2) Å, c = 5.447(3) Å, β = 92.551(3)∘, P21/c. 10a. a = 13.177(2) Å, b = 14.597(2) Å, c = 5.5505(8) Å, β = 110.979(2)∘, Cc. 11a. a = 14.720(2) Å, b = 13.995(2) Å, c = 38.245(6) Å, β = 94.430(3)∘, P21/n. 12b. a = 15.067(5) Å, b = 20.378(6) Å, c = 8.669(5) Å, α = 99.16(4)∘, β = 99.32(3)∘, γ = 105.23(3)∘, P-1. 13b. a = 8.2824(6) Å, b = 10.5245(7) Å, c = 15.518(1) Å, α = 92.305(1)∘, β = 100.473(1)∘, γ = 100.124(1)∘, P-1. 15a. a = 15.357(3) Å, b = 7.778(2) Å, c = 22.957(2) Å, Pbca. 16b. a = 18.0384(4) Å, b = 12.474(3) Å, c = 20.078(5) Å, Pbca.

  N-苯基马来酰亚胺三唑衍生物的合成、性质和结构进行了描述。还讨论了中间体和副产品。1b. a = 43.997(7) Å，5.7610(9) Å，8.245(1) Å，β = 99.339(4)°，C2/c；2a. a = 13.646(4) Å，b = 7.744(2) Å，c = 10.612(3) Å，β = 91.979(6)°，P21/c。3a. a = 22.245(1) Å，b = 22.245(1) Å，10.010(1) Å，P42/n。3a′. a = 11.727(2) Å，b = 14.075(3) Å，c = 16.080(3) Å，α = 105.859(3)°，β = 105.331(3)°，γ = 98.187(3)°，P-1。3b. a = 8.561(3) Å，b = 14.755(5) Å，c = 22.771(7) Å，β = 97.006(5)°，P21/c。3c. a = 10.500(2) Å，b = 12.189(2) Å，c = 13.040(2) Å，α = 109.091(3)°，β = 106.089(3)°，γ = 101.022(3)°，P-1。8a. a = 16.389(8) Å，b = 5.749(3) Å，c = 19.316(3) Å，β = 97.467(9)°，P21/n。8b. a = 5.822(2) Å，b = 10.114(3) Å，c = 16.705(4) Å，α = 84.681(5)°，β = 82.840(5)°，γ = 75.769(4)°，P-1。9b. a = 11.251(1) Å，13.335(3) Å，13.376(3) Å，β = 102.456(4)°，P21/n。9c. a = 15.836(3) Å，b = 8.236(2) Å，c = 5.447(3) Å，β = 92.551(3)°，P21/c。10a. a = 13.177(2) Å，b = 14.597(2) Å，c = 5.5505(8) Å，β = 110.979(2)°，Cc。11a. a = 14.720(2) Å，b = 13.995(2) Å，c = 38.245(6) Å，β = 94.430(3)°，P21/n。12b. a = 15.067(5) Å，b = 20.378(6) Å，c = 8.669(5) Å，α = 99.16(4)°，β = 99.32(3)°，γ = 105.23(3)°，P-1。13b. a = 8.2824(6) Å，b = 10.5245(7) Å，c = 15.518(1) Å，α = 92.305(1)°，β = 100.473(1)°，γ = 100.124(1)°，P-1。15a. a = 15.357(3) Å，b = 7.778(2) Å，c = 22.957(2) Å，Pbca。16b. a = 18.0384(4) Å，b = 12.474(3) Å，c = 20.078(5) Å，Pbca。
• Color Tuning of the Aggregation-Induced Emission of Maleimide Dyes by Molecular Design and Morphology Control
  作者：Hiroaki Imoto、Kohei Kizaki、Seiji Watase、Kimihiro Matsukawa、Kensuke Naka

  DOI：10.1002/chem.201501519

  日期：2015.8.17

  Aggregation‐induced emission (AIE)‐active maleimide dyes, namely, 2‐p‐toluidino‐N‐p‐tolylmaleimide, 3‐phenyl‐2‐toluidino‐N‐p‐tolylmaleimide, 2‐p‐thiocresyl‐3‐p‐toluidino‐N‐p‐tolylmaleimide, and 2,3‐dithiocresyl‐N‐arylmaleimides, were synthesized by facile synthetic procedures. The dyes show intense emission in the solid state, and emission colors were controlled from green (λmax=527 nm) to orange (λmax=609 nm)

  聚集诱导发光（AIE）-active马来酰亚胺染料，即，2- p -toluidino- ñ - p -tolylmaleimide，3-苯基-2- toluidino- Ñ - p -tolylmaleimide，2- p -thiocresyl -3- p - toluidino- ñ - p -tolylmaleimide和2,3- dithiocresyl- ñ -arylmaleimides，通过简便的合成方法合成。染料显示出在固体状态下强发射，以及发光颜色从绿色控制（λ最大= 527纳米）到橙色（λ最大通过改变马来酰亚胺的2位和3位上的取代基以及固态堆积结构来改变= 609 nm）。2,3-二取代的马来酰亚胺染料有效地经历了其发射波长的红移。此外，一些染料表现出机械变色和多态性，并且它们的发射性质显着取决于固体样品的形态。通过X射线衍射研究了发射行为的机理。马来酰亚胺环上氮原子
• Inhibition of Bfl-1 with N-aryl maleimides
  作者：John R. Cashman、Mary MacDonald、Senait Ghirmai、Karl J. Okolotowicz、Eduard Sergienko、Brock Brown、Xochella Garcia、Dayong Zhai、Russell Dahl、John C. Reed

  DOI：10.1016/j.bmcl.2010.09.046

  日期：2010.11

  High-throughput screening of 66,000 compounds using competitive binding of peptides comprising the BH3 domain to anti-apoptotic Bfl-1 led to the identification of 14 validated 'hits' as inhibitors of Bfl-1. N-Aryl maleimide 1 was among the validated 'hits'. A chemical library encompassing over 280 analogs of 1 was prepared following a two-step synthesis. Structure-activity studies for inhibition of Bfl-1 by analogs of N-aryl maleimide 1 revealed a preference for electron-withdrawing substituents in the N-aryl ring and hydrophilic amines appended to the maleimide core. Inhibitors of Bfl-1 are potential development candidates for anti-cancer therapeutics. (C) 2010 Elsevier Ltd. All rights reserved.