(2,4,6-trimethylphenyl)maleamic acid | 55862-97-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2,4,6-trimethylphenyl)maleamic acid
• 英文别名: Maleinsaeure-mono-2,4,6-trimethyl-anilid；N-(2,4,6-Trimethylphenyl)maleamicacid；(Z)-4-oxo-4-(2,4,6-trimethylanilino)but-2-enoic acid
• CAS: 55862-97-0
• 化学式: C₁₃H₁₅NO₃
• 分子量: 233.267
• InChiKey: LIBBIQNPOBBNDV-PLNGDYQASA-N

物化性质

• 熔点：
  164 °C
• 沸点：
  443.0±45.0 °C(Predicted)
• 密度：
  1.211±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2,4,6-trimethylphenyl)maleamic acid 在 氯化亚砜 作用下， 以90%的产率得到3-chloro-1-mesitylpyrrolidine-2,5-dione
  参考文献：
  名称：

  3-氯-1-取代的芳基吡咯烷-2,5-二酮衍生物的合成：有效的人碳酸酐酶抑制剂的发现

  摘要：

  碳酸酐酶同工酶是重要的金属酶，涉及许多生理过程，它们通过金属氢氧化物的亲核机理催化二氧化碳（CO 2）可逆水合为碳酸氢根（HCO 3 –）和质子（H +）。由于它们已知的生物学活性和作为碳酸酐酶抑制剂的潜力，本研究集中于开发合成3-氯-1-芳基吡咯烷-2，5-二酮（2b）的便利途径。该合成路线始于（Z）-4-氧-4-（芳氨基）丁-2-烯酸（3b）和二氯化硫（SOCl 2），并导致闭环反应，产生了一系列3-氯-N-芳基马来酰亚胺衍生物（20 – 29），收率高。这是3-氯-1-芳基pyyrolidine -2,5-二酮类的合成的第一次报告20 - 23和27 - 29通过的（Z）闭环反应-4-氧代-4-（芳基氨基），但-2-烯酸 通过1 H-NMR，13 C-NMR和红外光谱确定所有产物的结构。研究了它们对人碳酸酐酶I和II的生物学活性。3-氯-1-芳基吡咯烷-2,5-二酮强烈抑制人碳酸酐酶I和II的活性，其中K

  DOI：

  10.1007/s00044-017-1865-2
• 作为产物：
  描述：

  马来酸酐 、 2,4,6-三甲基苯胺 以96%的产率得到(2,4,6-trimethylphenyl)maleamic acid
  参考文献：
  名称：

  （Z）-4-氧代-4-（芳基氨基）丁-2-烯酸衍生物的合成及其对人碳酸酐酶I和II同工酶的抑制特性的测定。

  摘要：

  提出了具有可用于合成多个活性分子的结构特征的（Z）-4-氧代-4-（芳基氨基）丁-2-烯酸（4）衍生物的合成。按照文献程序并在反应结束时合成一些丁烯酸衍生物（4a，4c，4e，4i，4j，4k）。另外，通过（1）H-NMR，（13）C-NMR和IR光谱确定所有合成衍生物（4a-4m）的结构。碳酸酐酶是一种涉及许多关键生理过程的金属酶，因为它催化一个简单但基本的反应，即二氧化碳可逆地水合成碳酸氢根和质子。通过评估这些衍生物对人碳酸酐酶hCA I和II同功酶（hCA I和II）的酶抑制活性，获得了重要的结果。

  DOI：

  10.3109/14756366.2015.1071808

文献信息

• 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.
• LOW AFFINITY SCREENING METHOD
  申请人：Graffinity Pharmaceuticals Aktiengesellschaft

  公开号：EP1360489A1

  公开（公告）日：2003-11-12
• Low affinity screening method
  申请人：——

  公开号：US20040082079A1

  公开（公告）日：2004-04-29

  A parallel high throughput screening method on a solid support is disclosed that allows the detection of low affinity binding partners, comprising the steps of:(a) providing a library of different ligands;(b) forming a binding matrix comprising the ligands on a solid support by immobilising said ligands on the support; (c) contacting a target of interest with said binding matrix; (d) parallely determining a binding value of the ligand/target interaction for each type of ligand comprised in the binding matrix; (e) selecting those ligands the binding value of which in an immobilised state towards the target exceeds a predetermined threshold; (f) evaluating the affinity of each of the ligands selected in step (e) in a non-immobilised state towards the target; (g) identifying at least one ligand of step (f) as low affinity binding ligand.
• US3948942A
  申请人：——

  公开号：US3948942A

  公开（公告）日：1976-04-06
• [EN] LOW AFFINITY SCREENING METHOD<br/>[FR] PROCEDE DE CRIBLAGE DES FAIBLES AFFINITES
  申请人：GRAFFINITY PHARM DESIGN GMBH

  公开号：WO2002063299A1

  公开（公告）日：2002-08-15

  A parallel high throughput screening method on a solid support is disclosed that allows the detection of low affinity binding partners, comprising the steps of:(a) providing a library of different ligands;(b) forming a binding matrix comprising the ligands on a solid support by immobilising said ligands on the support; (c) contacting a target of interest with said binding matrix; (d) parallely determining a binding value of the ligand/target interaction for each type of ligand comprised in the binding matrix; (e) selecting those ligands the binding value of which in an immobilised state towards the target exceeds a predetermined threshold; (f) evaluating the affinity of each of the ligands selected in step (e) in a non-immobilised state towards the target; (g) identifying at least one ligand of step (f) as low affinity binding ligand.