3-chloro-4-(4-chlorophenyl)-1H-pyrrole-2,5-dione | 4814-16-8

• 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: 3-chloro-4-(4-chlorophenyl)-1H-pyrrole-2,5-dione
• 英文别名: 2-(4-Chlorphenyl)-3-chlormaleinimid；3-chloro-4-(4-chlorophenyl)pyrrole-2,5-dione
• CAS: 4814-16-8
• 化学式: C₁₀H₅Cl₂NO₂
• 分子量: 242.061
• InChiKey: AWUHTLYFTXXFPW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 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：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-chloro-4-(4-chlorophenyl)-1H-pyrrole-2,5-dione 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 72.0h， 生成 2-Chloro-5-[4-(4-chloro-phenyl)-1-methyl-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-ylamino]-benzoic acid
  参考文献：
  名称：

  3-Anilino-4-arylmaleimides: potent and selective inhibitors of glycogen synthase kinase-3 (GSK-3)

  摘要：

  Potent 3-anilino-4-arylmaleimide glycogen synthase kinase-3 (GSK-3) inhibitors have been prepared using automated array methodology. A number of these are highly selective, having little inhibitory potency against more than 20 other protein kinases. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(00)00721-6
• 作为产物：
  描述：

  对氯苯乙酸甲酯 在 ammonium hydroxide 、 草酰氯 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 25.0h， 生成 3-chloro-4-(4-chlorophenyl)-1H-pyrrole-2,5-dione
  参考文献：
  名称：

  Synthesis of aryl anilinomaleimide based derivatives as glycogen synthase kinase-3β inhibitors with potential role as antidepressant agents

  摘要：

  基于新型苯胺马来酰亚胺衍生物被发现能抑制GSK-3β活性体外，并在动物模型中展现抗抑郁效果。

  DOI：

  10.1039/c5nj02896e

文献信息

• Synthesis, Cytotoxicity and Protein Kinase C Inhibition of Arylpyrrolylmaleimides
  作者：Gui-Qing Xu、Chong Zhang、Lei Zhang、Xing-Lu Zhou、Bo Yang、Qiao-Jun He、Yong-Zhou Hu

  DOI：10.1002/ardp.200700190

  日期：2008.5

  novel arylpyrrolylmaleimides was synthesized and evaluated for their in‐vitro cytotoxicity against various human cancer cell lines and their protein‐kinase C inhibitory activity. Some of the compounds showed high or moderate cytotoxic activity against the tested cell lines. Compound 6b is the most promising compound against the tested cancer cell lines; 6d and 6e showed moderate protein‐kinase C inhibition

  合成了一系列新型芳基吡咯基马来酰亚胺，并评估了它们对各种人类癌细胞系的体外细胞毒性及其蛋白激酶 C 抑制活性。一些化合物对测试的细胞系显示出高或中度的细胞毒活性。化合物 6b 是最有前途的抗癌细胞系化合物；6d和6e显示出中度蛋白激酶C抑制。根据获得的实验数据讨论结构 - 活性关系。
• Novel method and compounds
  申请人：SmithKline Beecham p.l.c.

  公开号：US20040010031A1

  公开（公告）日：2004-01-15

  A method for the treatment of conditions associated with a need for inhibition of GSK-3, such as diabetes, dementias such as Alzheimer's disease and manic depression which method comprises the administration of a pharmaceutically effective, non-toxic amount of a compound of formula (I): 1 or a pharmaceutically acceptable derivative thereof, wherein: R is hydrogen, alkyl, aryl, or aralkyl; R 1 is hydrogen, alkyl, aralkyl, hydroxyalkyl or alkoxyalkyl; R 2 is substituted or unsubstituted aryl or substituted or unsubstituted heterocyclyl; R 3 is hydrogen, substituted or unsubstituted alkyl, cycloalkyl, alkoxyalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclyl or aralkyl wherein the aryl moiety is substituted or unsubstituted; or, R 1 and R 3 together with the nitrogen to which they are attached form a single or fused, optionally substituted, saturated or unsaturated heterocylic ring; to a human or non-human mammal in need thereof, and compounds of formula I.

  一种用于治疗与需要抑制GSK-3相关的疾病的方法，例如糖尿病、阿尔茨海默病和躁郁症，该方法包括向需要的人类或非人类哺乳动物投予化学药效、无毒量的化合物(I)的药物，其中：R为氢、烷基、芳基或芳基烷基；R1为氢、烷基、芳基烷基、羟基烷基或烷氧基烷基；R2为取代或未取代的芳基或取代或未取代的杂环烷基；R3为氢、取代或未取代的烷基、环烷基、烷氧基烷基、取代或未取代的芳基、取代或未取代的杂环烷基或芳基烷基，其中芳基部分为取代或未取代；或者，R1和R3与它们连接的氮一起形成单个或融合的、可选择取代的饱和或不饱和杂环环；以及化合物I的药物可接受衍生物。
• [EN] PYRROLE-2,5-DIONE DERIVATIVES FOR THE TREATMENT OF DIABETES<br/>[FR] DERIVES DE PYRROLE-2, 5-DIONE DESTINES AU TRAITEMENT DU DIABETE
  申请人：SMITHKLINE BEECHAM PLC

  公开号：WO2001074771A1

  公开（公告）日：2001-10-11

  A method for the treatment of conditions associated with a need for inhibition of GSK-3, which method comprises the administration of a pharmaceutically effective, non-toxic amount of a compound of formula (I) or a pharmaceutically acceptable derivative thereof, wherein R1 is a substituted or unsubstituted carbocyclic or heterocyclic aromatic ring, which ring may be fused to a substituted or unsubstituted carbocyclic or heterocyclic aromatic or non-aromatic ring; R2 is a substituted or unsubstituted carbocyclic or heterocyclic aromatic ring, which ring may be fused to a substituted or unsubstituted carbocyclic or heterocyclic aromatic ring, with the proviso that R2 is not 3-indolyl or a fused-ring derivative of 3-indolyl; R3 is hydrogen, or R?1 and R3¿ together with the nitrogen atom to which they are attached form a fused substituted or unsubstituted heterocylic ring; to a human or non-human mammal in need thereof.

  一种用于治疗需要抑制GSK-3的病症的方法，该方法包括向需要治疗的人类或非人哺乳动物中投与一种公认为药用的衍生物或化合物(I)的有效、非毒性剂量，其中R1是取代或未取代的碳环或杂环芳香环，该环可能与取代或未取代的碳环或杂环芳香环或非芳香环融合；R2是取代或未取代的碳环或杂环芳香环，该环可能与取代或未取代的碳环或杂环芳香环融合，但R2不是3-吲哚基或3-吲哚基的融合环衍生物；R3是氢，或R1和R3与它们连接的氮原子一起形成融合的取代或未取代的杂环环。
• Method and compounds
  申请人：SmithKline Beecham Corporation

  公开号：US06719520B2

  公开（公告）日：2004-04-13

  A method for the treatment of conditions associated with a need for inhibition of GSK-3, such as diabetes, dementias such as Alzheimer's disease and manic depression which method comprises the administration of a pharmaceutically effective, non-toxic amount of a compound of formula (I): or a pharmaceutically acceptable derivative thereof, wherein: R is hydrogen, alkyl, aryl, or aralkyl; R1 is hydrogen, alkyl, aralkyl, hydroxyalkyl or alkoxyalkyl; R2 is substituted or unsubstituted aryl or substituted or unsubstituted heterocyclyl; R3 is hydrogen, substituted or unsubstituted alkyl, cycloalkyl, alkoxyalkyl, substituted or unsubstituted aryl, substituted or unsubstituted heterocyclyl or aralkyl wherein the aryl moiety is substituted or unsubstituted; or, R1 and R3 together with the nitrogen to which they are attached form a single or fused, optionally substituted, saturated or unsaturated heterocylic ring; to a human or non-human mammal in need thereof, and compounds of formula I.

  一种用于治疗与需要抑制GSK-3相关的疾病的方法，例如糖尿病，老年痴呆症，躁郁症，该方法包括给予一种公式（I）化合物或其药学上可接受的衍生物的药学有效、无毒剂量，其中：R是氢、烷基、芳基或芳基烷基；R1是氢、烷基、芳基烷基、羟基烷基或烷氧基烷基；R2是取代或未取代的芳基或取代或未取代的杂环基；R3是氢、取代或未取代的烷基、环烷基、烷氧基烷基、取代或未取代的芳基、取代或未取代的杂环基或芳基烷基，其中芳基基团是取代或未取代的；或者，R1和R3与它们所连接的氮一起形成单个或融合的、可选取代的、饱和或不饱和的杂环环；给予需要该方法的人类或非人哺乳动物，以及公式I化合物。
• Targeting multidrug resistant <i>Staphylococcus</i> infections with bacterial histidine kinase inhibitors
  作者：Adeline Espinasse、Manibarsha Goswami、Junshu Yang、Onanong Vorasin、Yinduo Ji、Erin E. Carlson

  DOI：10.1039/d2sc05369a

  日期：——

  We report an anti-virulence strategy to target methicillin-resistant Staphylococcus aureus (MRSA). The most potent lead decreased the lesion size caused by a MRSA skin infection by 65% in a mouse model.

  我们报告了一种针对耐甲氧西林金黄色葡萄球菌（MRSA）的抗病毒策略。在小鼠模型中，最有效的先导物使 MRSA 皮肤感染引起的病变面积缩小了 65%。