7-氯-4-羟基-8-甲基喹啉-3-羧酸乙酯 | 5350-94-7

• 物质功能分类: 医药中间体 - 杂环化合物 - 喹啉类化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 中文名称: 7-氯-4-羟基-8-甲基喹啉-3-羧酸乙酯
• 中文别名: 7-氯-4-羟基-8-甲基-3-喹啉羧酸乙酯
• 英文名称: Ethyl 7-chloro-4-hydroxy-8-methylquinoline-3-carboxylate
• 英文别名: ethyl 7-chloro-8-methyl-4-oxo-1H-quinoline-3-carboxylate
• CAS: 5350-94-7；302948-99-8
• 化学式: C₁₃H₁₂ClNO₃
• mdl: MFCD01912282
• 分子量: 265.696
• InChiKey: HOKMOQAMIGSWSJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 海关编码：
  2933499090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  7-氯-4-羟基-8-甲基喹啉-3-羧酸乙酯 在 氯化亚砜 、 N,N-二异丙基乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 7.0h， 生成 4-[benzyl(methyl)amino]-7-chloro-8-methylquinoline-3-carboxylic acid
  参考文献：
  名称：

  新規キノリンカルボン酸誘導体及びこれを含有する医薬

  摘要：

  【问题】提供一种抑制淀粉样纤维形成的化合物，包括该化合物的淀粉样纤维形成抑制剂以及神经变性疾病的治疗药物或预防药物。 【解决方案】化合物由式（I）表示。 [其中，X是-（CH2）n-; n是0〜3的整数; Y是双键或二价连接基，例如烷基等; Ar是取代/未取代的苯基或吡啶基; R1是取代/未取代的烷基; Ar和R1，Ar和Y或R1和Y可以共同形成环; R2〜R4分别是独立的H，C1-20烷基等] 【图示】无

  公开号：

  JP2018168083A
• 作为产物：
  描述：

  3-氯-2-甲基苯胺 以 various solvent(s) 为溶剂， 反应 2.0h， 生成 7-氯-4-羟基-8-甲基喹啉-3-羧酸乙酯
  参考文献：
  名称：

  Evaluation of 3-Carboxy-4(1H)-quinolones as Inhibitors of Human Protein Kinase CK2

  摘要：

  Due to the emerging role of protein kinase CK2 as a molecule that participates not only in the development of some cancers but also in viral infections and inflammatory failures, small organic inhibitors of CK2, besides application in scientific research, may have therapeutic significance. In this paper, we present a new class of CK2 inhibitorss3-carboxy-4(1H)-quinolones. This class of inhibitors has been selected via receptor-based virtual screening of the Otava compound library. It was revealed that the most active compounds, 5,6,8-trichloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (7) (IC50 = 0.3 mu M) and 4-oxo-1,4-dihydrobenzo[h] quinoline-3-carboxylic acid (9) (IC50 = 1 AM), are ATP competitive (K-i values are 0.06 and 0.28 mu M, respectively). Evaluation of the inhibitors on seven protein kinases shows considerable selectivity toward CK2. According to theoretical calculations and experimental data, a structural model describing the key features of 3-carboxy-4(1H)-quinolones responsible for tight binding to CK2 active site has been developed.

  DOI：

  10.1021/jm050048t

文献信息

• Investigations on the 4-Quinolone-3-carboxylic Acid Motif. 2. Synthesis and Structure−Activity Relationship of Potent and Selective Cannabinoid-2 Receptor Agonists Endowed with Analgesic Activity in Vivo
  作者：Serena Pasquini、Lorenzo Botta、Teresa Semeraro、Claudia Mugnaini、Alessia Ligresti、Enza Palazzo、Sabatino Maione、Vincenzo Di Marzo、Federico Corelli

  DOI：10.1021/jm800552f

  日期：2008.8.1

  Quinolone-3-carboxamides 11 bearing at position 5, 6, 7, or 8 diverse substituents such as halides, alkyl, aryl, alkoxy, and aryloxy groups differing in their steric/electronic properties, were prepared. The new compounds were tested in vitro for CB1 and CB2 receptor affinity in comparison with the reference compounds rimonabant and SR144528. The tested compounds exhibited CB2 affinity in the ran, e from 55.9 to 0.8 nM and CB1 affinity in the range from > 10 000 to 5.3 nM, with selectivity indeces [K-i(CB1)/K-i(CB2)] varying from > 2666.6 to 1.23. On the basis of the structure-selectivity relationship developed, the presence of a substituent at C6/C8 or C7 well accounts for the high or low CB2 selectivity, respectively. Compound 11c, characterized by high CB2 affinity and selectivity, showed analgesic activity in the formalin test of acute peripheral and inflammatory pain in mice as a result of selective CB2 agonistic activity.
• Evaluation of 3-Carboxy-4(1<i>H</i>)-quinolones as Inhibitors of Human Protein Kinase CK2
  作者：Andriy G. Golub、Olexander Ya. Yakovenko、Volodymyr G. Bdzhola、Vladislav M. Sapelkin、Piotr Zien、Sergiy M. Yarmoluk

  DOI：10.1021/jm050048t

  日期：2006.11.1

  Due to the emerging role of protein kinase CK2 as a molecule that participates not only in the development of some cancers but also in viral infections and inflammatory failures, small organic inhibitors of CK2, besides application in scientific research, may have therapeutic significance. In this paper, we present a new class of CK2 inhibitorss3-carboxy-4(1H)-quinolones. This class of inhibitors has been selected via receptor-based virtual screening of the Otava compound library. It was revealed that the most active compounds, 5,6,8-trichloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (7) (IC50 = 0.3 mu M) and 4-oxo-1,4-dihydrobenzo[h] quinoline-3-carboxylic acid (9) (IC50 = 1 AM), are ATP competitive (K-i values are 0.06 and 0.28 mu M, respectively). Evaluation of the inhibitors on seven protein kinases shows considerable selectivity toward CK2. According to theoretical calculations and experimental data, a structural model describing the key features of 3-carboxy-4(1H)-quinolones responsible for tight binding to CK2 active site has been developed.
• 新規キノリンカルボン酸誘導体及びこれを含有する医薬
  申请人：国立研究開発法人国立長寿医療研究センター

  公开号：JP2018168083A

  公开（公告）日：2018-11-01

  【課題】アミロイド線維の形成を抑制する化合物、当該化合物を含むアミロイド線維形成抑制剤および神経変性疾患の治療薬または予防薬の提供。【解決手段】式（Ｉ）で表される化合物。［Ｘは−（ＣＨ２）ｎ−；ｎは０〜３の整数；Ｙは単結合又はアルキル基等の２価の連結基；Ａｒは置換／非置換のフェニル基又はピリグル基；Ｒ１は置換／非置換のアルキル基；Ａｒ及びＲ１、Ａｒ及びＹ又はＲ１及びＹは、共同して環を形成してもよい；Ｒ２〜Ｒ４は夫々独立にＨ、Ｃ１−２０アルキル基等］【選択図】なし

  【问题】提供一种抑制淀粉样纤维形成的化合物，包括该化合物的淀粉样纤维形成抑制剂以及神经变性疾病的治疗药物或预防药物。 【解决方案】化合物由式（I）表示。 [其中，X是-（CH2）n-; n是0〜3的整数; Y是双键或二价连接基，例如烷基等; Ar是取代/未取代的苯基或吡啶基; R1是取代/未取代的烷基; Ar和R1，Ar和Y或R1和Y可以共同形成环; R2〜R4分别是独立的H，C1-20烷基等] 【图示】无