(N-methyl-anilinomethylene)-malonic acid diethyl ester | 37041-15-9

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (N-methyl-anilinomethylene)-malonic acid diethyl ester
• 英文别名: (N-Methyl-anilinomethylen)-malonsaeure-diaethylester；diethyl N-methyl-N-phenylaminomethylenemalonate；Diethyl {[methyl(phenyl)amino]methylidene}propanedioate；diethyl 2-[(N-methylanilino)methylidene]propanedioate
• CAS: 37041-15-9
• 化学式: C₁₅H₁₉NO₄
• 分子量: 277.32
• InChiKey: GIDDHVVEGZZYOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (N-methyl-anilinomethylene)-malonic acid diethyl ester 以 various solvent(s) 为溶剂， 反应 1.0h， 生成 ethyl 1-methyl-1,4-dihydro-4-oxoquinoline-3-carboxylate
  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
• 作为产物：
  描述：

  2-苯基氨基亚甲基-丙二酸二乙酯 、 碘甲烷 在 sodium hydride 、 甲醇 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 (N-methyl-anilinomethylene)-malonic acid diethyl ester
  参考文献：
  名称：

  Novel 3-(4-oxo-4h-chromen-2-yl)-(1H)-quinolin-4-one derivatives, method for preparing same and pharmaceutical compositions containing same

  摘要：

  化合物的化学式（I）如下：其中：R1、R2、R3、R4、R6、R8、R9和R10，可能相同也可能不同，每个代表从氢、羟基、烷氧基、烷基、芳基烷氧基、烷氧羰基烷氧基和OR′中选择的一个基团，其中R′代表一个被电离或可电离的基团，R5代表从烷基、芳基和杂环烷基中选择的一个基团，R7代表从氢、羟基、烷氧基、烷基和环烷基中选择的一个基团，或者R7代表含氮或含氧的杂环，其光学异构体、水合物和溶剂合物以及与药用酸或碱形成的加合物。包含这些化合物的药物产品可用作抗癌剂。

  公开号：

  US20060063801A1

文献信息

• Huppatz, John L.; Phillips, John N.; Rattigan, Barbara M., Agricultural and Biological Chemistry, 1981, vol. 45, # 12, p. 2769 - 2774
  作者：Huppatz, John L.、Phillips, John N.、Rattigan, Barbara M.

  DOI：——

  日期：——
• The Reduction of Amide Vinylogs
  作者：Robert H. Baker、Arthur H. Schlesinger

  DOI：10.1021/ja01214a041

  日期：1946.10
• Addition of Lithiated Acetonitrile to β-Substituted Methylenemalonates. Revision and Correction
  作者：Peter Stanetty、Manfred Kremslehner、Horst Völlenkle

  DOI：10.1007/pl00000087

  日期：1998.3
• US7339061B2
  申请人：——

  公开号：US7339061B2

  公开（公告）日：2008-03-04
• 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.