4-((3,4-dichlorophenyl)amino)-2-methylene-4-oxobutanoic acid | 74448-36-5

• 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: 4-((3,4-dichlorophenyl)amino)-2-methylene-4-oxobutanoic acid
• 英文别名: 4-(3,4-Dichloroanilino)-2-methylidene-4-oxobutanoic acid
• CAS: 74448-36-5
• 化学式: C₁₁H₉Cl₂NO₃
• 分子量: 274.103
• InChiKey: RRYLHAFQNJUGBV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.09
• 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：

  4-((3,4-dichlorophenyl)amino)-2-methylene-4-oxobutanoic acid 生成 Methyl N-(3,4-dichlorophenyl)-2-methylenesuccinamate
  参考文献：
  名称：

  DISDIER, A.;BORROD, G.;TRINH, S.

  摘要：

  DOI：
• 作为产物：
  描述：

  衣康酸酐 生成 4-((3,4-dichlorophenyl)amino)-2-methylene-4-oxobutanoic acid
  参考文献：
  名称：

  DISDIER, A.;BORROD, G.;TRINH, S.

  摘要：

  DOI：

文献信息

• Substituted N-phenylitaconamides as inhibitors of mycobacteria and mycobacterial isocitrate lyase
  作者：Martin Krátký、Eva Novotná、Jiřina Stolaříková、Markéta Švarcová、Jarmila Vinšová

  DOI：10.1016/j.ejps.2022.106252

  日期：2022.9

  efficacy with minimum inhibitory concentrations starting from 125 µM. M. kansasii was the most susceptible species. Itaconamides derived from sulfonamides or p-aminosalicylic acid were optimal for activity against extracellular mycobacteria. ICL1 was significantly inhibited by two compounds, with 2-methylene-4-[(4-nitrophenyl)amino]-4-oxobutanoic acid 1k being the most potent (36% inhibition at 10 µM),

  需要新的抗分枝杆菌药物，尤其是那些对活跃生长和非复制的分枝杆菌亚群具有双重活性的药物。异柠檬酸裂合酶 (ICL) 是建议的靶点之一，该酶被衣康酸抑制。这就是为什么我们设计和制备了 16 种衣康酸酰胺以及各种苯胺和胺类抗菌药物，以评估它们作为 ICL 的潜在抑制剂和抗分枝杆菌药物的原因。N -Phenylitaconamides 由衣康酸酐和取代的苯胺制备（产率 57-99%）。他们针对分枝杆菌 ICL 和活跃生长的分枝杆菌（结核分枝杆菌H 37 Rv、鸟分枝杆菌、堪萨斯分枝杆菌的两种菌株）进行了表征和评估）。所有衍生物均显示出抗分枝杆菌功效，最低抑制浓度从 125 µM 开始。M. kansasii是最易感的物种。源自磺胺类或对氨基水杨酸的衣康酰胺对细胞外分枝杆菌的活性是最佳的。ICL1 受到两种化合物的显着抑制，其中 2-methylene-4-[(4-nitrophenyl)amino]-4-oxobutanoic
• Veverka, Miroslav; Kralovicova, Eva, Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 10, p. 2731 - 2737
  作者：Veverka, Miroslav、Kralovicova, Eva

  DOI：——

  日期：——
• <i>N</i>-Aryl-3-mercaptosuccinimides as Antivirulence Agents Targeting <i>Pseudomonas aeruginosa</i> Elastase and <i>Clostridium</i> Collagenases
  作者：Jelena Konstantinović、Samir Yahiaoui、Alaa Alhayek、Jörg Haupenthal、Esther Schönauer、Anastasia Andreas、Andreas M. Kany、Rolf Müller、Jesko Koehnke、Fabian K. Berger、Markus Bischoff、Rolf W. Hartmann、Hans Brandstetter、Anna K. H. Hirsch

  DOI：10.1021/acs.jmedchem.0c00584

  日期：2020.8.13

  In light of the global antimicrobial-resistance crisis, there is an urgent need for novel bacterial targets and antibiotics with novel modes of action. It has been shown that Pseudomonas aeruginosa elastase (LasB) and Clostridium histolyticum (Hathewaya histolytica) collagenase (CoIH) play a significant role in the infection process and thereby represent promising antivirulence targets. Here, we report novel N-aryl-3-mercaptosuccinimide inhibitors that target both LasB and CoIH, displaying potent activities in vitro and high selectivity for the bacterial over human metalloproteases. Additionally, the inhibitors demonstrate no signs of cytotoxicity against selected human cell lines and in a zebrafish embryo toxicity model. Furthermore, the most active CoIH inhibitor shows a significant reduction of collagen degradation in an ex vivo pig-skin model.
• US4431442A
  申请人：——

  公开号：US4431442A

  公开（公告）日：1984-02-14