4-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide | 84088-17-5

• 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-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide
• 英文别名: PNU 211944；N-phenyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-quinoline-3-carboxamide；4-hydroxy-1-methyl-2-oxo-N-phenylquinoline-3-carboxamide
• CAS: 84088-17-5
• 化学式: C₁₇H₁₄N₂O₃
• 分子量: 294.31
• InChiKey: SCIYKTDXFNBCIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  69.6
• 氢给体数：
  2
• 氢受体数：
  3

ADMET

代谢

4-羟基-1-甲基-2-氧代-N-苯基-1,2-二氢喹啉-3-甲酰胺是林诺米德的已知人体代谢物。

4-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide is a known human metabolite of linomide.

来源:NORMAN Suspect List Exchange

反应信息

• 作为反应物：
  描述：

  4-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide 在 溴 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以82%的产率得到4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid 4-bromoanilide
  参考文献：
  名称：

  4-hydroxy-2-quinolones. 110. Bromination of 1-r-4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acid anilides

  摘要：

  DOI：

  10.1007/s10593-006-0239-3
• 作为产物：
  描述：

  1-甲基苯唑 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 6.5h， 生成 4-hydroxy-1-methyl-2-oxo-N-phenyl-1,2-dihydroquinoline-3-carboxamide
  参考文献：
  名称：

  Structure–activity relationships studies of the anti-angiogenic activities of linomide

  摘要：

  The synthesis and anti-angiogenic activities of linomide and its analogues are reported. Three of the analogues are 3.3-69 times more potent than linomide at inhibiting blood vessel formation in the CAM angiogenesis assay. These compounds possessed considerable anti-proliferative activity against isolated HUVEC cells with no activity against epithelial-derived prostate tumor cells. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00047-7

文献信息

• N-Phenyl-4-hydroxy-2-quinolone-3-carboxamides as selective inhibitors of mutant H1047R phosphoinositide-3-kinase (PI3Kα)
  作者：Dima A. Sabbah、Neka A. Simms、Wang Wang、Yuxiang Dong、Edward L. Ezell、Michael G. Brattain、Jonathan L. Vennerstrom、Haizhen A. Zhong

  DOI：10.1016/j.bmc.2012.09.059

  日期：2012.12

  efforts to optimize the lead PI3Kα inhibitor N-benzyl 4-hydroxy-2-quinolone-3-carboxamide using structure-based design and molecular docking. We identified a series of N-phenyl 4-hydroxy-2-quinolone-3-carboxamides as selective inhibitors of mutant H1047R versus wild-type PI3Kα and we also showed that the cell growth inhibition by these compounds likely occurs by inhibiting the formation of pAKT and induction

  这项工作描述了我们使用基于结构的设计和分子对接来优化先导 PI3Kα 抑制剂N-苄基 4-羟基-2-喹诺酮-3-甲酰胺的努力。我们鉴定了一系列N-苯基 4-羟基-2-喹诺酮-3-甲酰胺作为突变体 H1047R 与野生型 PI3Kα 的选择性抑制剂，我们还表明这些化合物可能通过抑制 pAKT 的形成来抑制细胞生长和诱导细胞凋亡。
• [EN] 1,2-DIHYDRO-4-HYDROXY-2-OXO-QUINOLINE-3-CARBOXANILIDES AS AHR ACTIVATORS.<br/>[FR] 1,2-DIHYDRO-4-HYDROXY-2-OXO-QUINOLÉINE-3-CARBOXANILIDES EN TANT QU'ACTIVATEURS D'AHR
  申请人：PETTERSSON LARS

  公开号：WO2012050500A1

  公开（公告）日：2012-04-19

  The present invention relates to compounds which are 1, 2-dihydro-4- hydroxy-2-oxo-quinoline-3-carboxanilides, their thieno-pyridone analogs, and prodrugs thereof. This invention specifically relates to such derivatives containing an N-hydrogen in the carboxanilide moiety and which exhibit modulating activity towards the aromatic hydrocarbon receptor (AhR), and, specifically, also to prodrugs thereof. The present invention also relates to use of said compounds as a medicament, and for the treatment of cancer, autoimmune disorders and other disorders with an immunological component, and a pharmaceutical composition comprising one or more of said compounds and a method of treatment.

  本发明涉及化合物，其为1,2-二氢-4-羟基-2-氧基喹啉-3-羧酰苯胺，其噻吩-吡啶酮类似物及其前药。本发明具体涉及含有羧酰苯胺基团中N-氢的衍生物，具有对芳香烃受体（AhR）的调节活性，特别是还涉及其前药。本发明还涉及将所述化合物用作药物，用于治疗癌症、自身免疫性疾病和其他具有免疫成分的疾病，以及包含一种或多种所述化合物的药物组合物和治疗方法。
• 다이하이드로퀴놀린 카복스아마이드 유도체 또는 이의 약학적으로 허용 가능한 염을 유효성분으로 포함하는 폐렴의 예방 또는 치료용 약학적 조성물
  申请人：KOREA RESEARCH INSTITUTE OF CHEMICAL TECHNOLOGY 한국화학연구원(319980077651)

  公开号：KR20190067546A

  公开（公告）日：2019-06-17

  다이하이드로퀴놀린 카복스아마이드 유도체 또는 이의 약학적으로 허용 가능한 염을 유효성분으로 포함하는 폐렴의 예방 또는 치료용 약학적 조성물이 개시된다. 상기 약학적 조성물은 우수한 항균활성을 가질 뿐만 아니라, 종래 일반적으로 사용되고 있는 에리트로마이신과 같은 항균제와는 달리 약물내성을 가지는 폐렴균에 대하여 항균 활성이 뛰어나므로 이들 폐렴균에 의해서 발생되는 폐렴 질환의 예방 또는 치료용 약학적 조성물로써 유용하게 사용될 수 있다.

  二羟基喹诺啉羧酰胺衍生物或其药学上允许的盐作为有效成分，用于预防或治疗肺炎的药学组合物已经公开。该药学组合物不仅具有优异的抗菌活性，而且对于对传统抗生素如红霉素等常用抗菌剂具有药物耐药性的肺炎菌具有出色的抗菌活性，因此可以作为预防或治疗由这些肺炎菌引起的肺炎疾病的药学组合物而被有益地使用。
• Heterocyclic carboxamides, compositions containing such compounds,
  申请人：Aktiebolaget Leo

  公开号：US04547511A1

  公开（公告）日：1985-10-15

  This invention relates to novel heterocyclic carboxamides which increase the activity of the immune system and to the preparation thereof. The invention is also concerned with pharmaceutical compositions containing the said compounds and methods of treatment therewith.

  本发明涉及一种新型杂环羧酰胺，其能够增强免疫系统的活性，以及其制备方法。本发明还涉及含有上述化合物的药物组合物和治疗方法。
• 1,2-DIHYDRO-4-HYDROXY-2-OXO-QUINOLINE-3-CARBOXANILIDES AS AHR ACTIVATORS
  申请人：Pettersson Lars

  公开号：US20130203703A1

  公开（公告）日：2013-08-08

  The present invention relates to compounds which are 1,2-dihydro-4-hydroxy-2-oxo-quinoline-3-carboxanilides, their thieno-pyridone analogs, and prodrugs thereof. This invention specifically relates to such derivatives containing an N-hydrogen in the carboxanilide moiety and which exhibit modulating activity towards the aromatic hydrocarbon receptor (AhR), and, specifically, also to prodrugs thereof. The present invention also relates to use of said compounds as a medicament, and for the treatment of cancer, autoimmune disorders and other disorders with an immunological component, and a pharmaceutical composition comprising one or more of said compounds and a method of treatment.

  本发明涉及1,2-二氢-4-羟基-2-氧代-喹啉-3-羧酰苯胺类化合物、其噻吩-吡啶酮类似物以及它们的前药。本发明具体涉及含有羧酰苯胺基团中的N-氢的衍生物，它们表现出对芳香族碳氢受体（AhR）的调节活性，以及它们的前药。本发明还涉及所述化合物作为药物的用途，用于治疗癌症、自身免疫性疾病以及其他具有免疫学成分的疾病，以及一种包含一种或多种所述化合物的药物组合物和一种治疗方法。