2-(((4-ethylphenyl)amino)methylene)diethyl malonate | 111186-10-8

• 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: 2-(((4-ethylphenyl)amino)methylene)diethyl malonate
• 英文别名: diethyl 4-ethylanilinomethylenemalonate；Diethyl 2-[(4-ethylanilino)methylidene]propanedioate
• CAS: 111186-10-8
• 化学式: C₁₆H₂₁NO₄
• 分子量: 291.347
• InChiKey: KKXKOMAWTNFTJC-UHFFFAOYSA-N

物化性质

• 沸点：
  363.9±42.0 °C(Predicted)
• 密度：
  1.130±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-(((4-ethylphenyl)amino)methylene)diethyl malonate 以 二苯醚 为溶剂， 反应 1.0h， 以37%的产率得到6-乙基-4-羟基喹啉-3-羧酸乙酯
  参考文献：
  名称：

  2- [ 18 F]氟乙基叠氮化物在施陶丁格连接中的用途–结合GABA A受体的4-喹诺酮的制备和表征

  摘要：

  标记试剂2- [ 18 F]氟乙基叠氮化物用于无痕Staudinger连接。该反应用于获得结合了6-苄基-4-氧代-1，4-二氢喹啉-3-羧酸（2- [ 18 F]氟乙基）酰胺的GABA A受体。制备的放射性示踪剂的无衰减校正放射化学产率为7％，放射化学纯度> 95％，比放射性为0.9 GBq /μmol。该化合物在正常大鼠中脑渗透率低。还已经制备了一系列对GABA A受体具有纳摩尔至亚纳摩尔亲和力的氟代烷基4-喹诺酮类似物。

  DOI：

  10.1016/j.bmcl.2010.05.106
• 作为产物：
  描述：

  乙氧基甲叉丙二酸二乙酯 、 4-乙基苯胺 反应 3.0h， 生成 2-(((4-ethylphenyl)amino)methylene)diethyl malonate
  参考文献：
  名称：

  2- [ 18 F]氟乙基叠氮化物在施陶丁格连接中的用途–结合GABA A受体的4-喹诺酮的制备和表征

  摘要：

  标记试剂2- [ 18 F]氟乙基叠氮化物用于无痕Staudinger连接。该反应用于获得结合了6-苄基-4-氧代-1，4-二氢喹啉-3-羧酸（2- [ 18 F]氟乙基）酰胺的GABA A受体。制备的放射性示踪剂的无衰减校正放射化学产率为7％，放射化学纯度> 95％，比放射性为0.9 GBq /μmol。该化合物在正常大鼠中脑渗透率低。还已经制备了一系列对GABA A受体具有纳摩尔至亚纳摩尔亲和力的氟代烷基4-喹诺酮类似物。

  DOI：

  10.1016/j.bmcl.2010.05.106

文献信息

• PHARMACEUTICAL COMPOSITION AND APPLICATION REPLACING QUINOLONE DERIVATIVE, PHARMACEUTICAL ACCEPTABLE SALT, OR STEREOISOMER
  申请人：Jinan University

  公开号：EP3339294A1

  公开（公告）日：2018-06-27

  Provided are a substituted quinolone derivative as shown by formula (I), or a pharmaceutically acceptable salt and a prodrug molecule thereof, and a pharmaceutical composition thereof, as well as the use of same in preparing drugs for the prevention and treatment of a tumor. The quinolone derivative, salt, prodrug molecule, and pharmaceutical composition thereof can be used as a protein kinase inhibitor, which is effective in inhibiting the activity of AXL protein kinase, and is capable of inhibiting the proliferation, migration and invasion of various tumor cells; and can be used in the preparation of anti-tumor drugs, especially drugs for treating hyperproliferative diseases such as a tumor in human beings and other mammals.

  本发明提供了一种如式（I）所示的取代喹诺酮衍生物或其药学上可接受的盐和原药分子及其药物组合物，以及其在制备预防和治疗肿瘤药物中的用途。本发明的喹诺酮衍生物、盐、原药分子及其药物组合物可用作蛋白激酶抑制剂，能有效抑制AXL蛋白激酶的活性，能够抑制各种肿瘤细胞的增殖、迁移和侵袭；可用于制备抗肿瘤药物，特别是用于治疗人类和其他哺乳动物的肿瘤等过度增殖性疾病的药物。
• Substituted quinolone derivatives, or pharmaceutically acceptable salts or stereoisomers thereof, and pharmaceutical compositions and use thereof
  申请人：JINAN UNIVERSITY

  公开号：US10683278B2

  公开（公告）日：2020-06-16

  Provided are a substituted quinolone derivative as shown by formula (I), or a pharmaceutically acceptable salt and a prodrug molecule thereof, and a pharmaceutical composition thereof, as well as the use of same in preparing drugs for the prevention and treatment of a tumor. The quinolone derivative, salt, prodrug molecule, and pharmaceutical composition thereof can be used as a protein kinase inhibitor, which is effective in inhibiting the activity of AXL protein kinase, and is capable of inhibiting the proliferation, migration and invasion of various tumor cells; and can be used in the preparation of anti-tumor drugs, especially drugs for treating hyperproliferative diseases such as a tumor in human beings and other mammals.

  本发明提供了一种如式（I）所示的取代喹诺酮衍生物或其药学上可接受的盐和原药分子及其药物组合物，以及其在制备预防和治疗肿瘤药物中的用途。本发明的喹诺酮衍生物、盐、原药分子及其药物组合物可用作蛋白激酶抑制剂，能有效抑制AXL蛋白激酶的活性，能够抑制各种肿瘤细胞的增殖、迁移和侵袭；可用于制备抗肿瘤药物，特别是用于治疗人类和其他哺乳动物的肿瘤等过度增殖性疾病的药物。
• [EN] PHARMACEUTICAL COMPOSITION AND APPLICATION REPLACING QUINOLONE DERIVATIVE, PHARMACEUTICAL ACCEPTABLE SALT, OR STEREOISOMER<br/>[FR] COMPOSITION PHARMACEUTIQUE ET APPLICATION REMPLAÇANT UN DÉRIVÉ DE QUINOLONE, SEL PHARMACEUTIQUEMENT ACCEPTABLE, OU STÉRÉOISOMÈRE<br/>[ZH] 取代喹诺酮类衍生物或其药学上可接受的盐或立体异构体及其药用组合物和应用
  申请人：UNIV JINAN

  公开号：WO2017028797A1

  公开（公告）日：2017-02-23

  提供了式（I）所示的取代喹诺酮类衍生物或其药学上可接受的盐、前药分子及其药用组合物和在制备防治肿瘤药物中的应用。所述喹诺酮类衍生物、盐、前药分子及其药用组合物可作为蛋白激酶抑制剂，有效抑制AXL蛋白激酶的活性并且能抑制多种肿瘤细胞的增殖、迁移和侵袭；可用于制备抗肿瘤药物，特别是制备治疗人类及其它哺乳动物的肿瘤等过度增殖性疾病的药物中。
• Synthesis and biological evaluation of 4-oxoquinoline-3-carboxamides derivatives as potent anti-fibrosis agents
  作者：Jun Zhu、Lin He、Liang Ma、Zhe Wei、Jiqiang He、Zhuang Yang、Yuzhi Pu、Dong Cao、Yuzhe Wu、Mingli Xiang、Aihua Peng、Yuquan Wei、Lijuan Chen

  DOI：10.1016/j.bmcl.2014.10.071

  日期：2014.12

  Thirty-one 4-oxoquinoline-3-carboxamides derivatives were synthesized and evaluated for their anti-fibrotic activities by the inhibition of TGF-beta 1-induced total collagen accumulation and anti-inflammatory activities by the inhibition of LPS-stimulated TNF-alpha production. Among them, three compounds (10a, 10l and 11g) exhibited potent inhibitory effects on both TGF-beta 1-induced total collagen accumulation and LPS-stimulated TNF-a production. Furthermore, oral administrations of 10l at a dose of 20 mg/kg/day for 4 weeks effectively alleviated lung inflammation and injury, and decreased lung collagen accumulation in bleomycin-induced pulmonary fibrosis model. Histopathological evaluation of lung tissue confirmed 10l as a potential, orally active agent for the treatment of pulmonary fibrosis. (C) 2014 Elsevier Ltd. All rights reserved.
• 4-Quinolone Derivatives:  High-Affinity Ligands at the Benzodiazepine Site of Brain GABA_A Receptors. Synthesis, Pharmacology, and Pharmacophore Modeling
  作者：Erik Lager、Pierre Andersson、Jakob Nilsson、Ingrid Pettersson、Elsebet Østergaard Nielsen、Mogens Nielsen、Olov Sterner、Tommy Liljefors

  DOI：10.1021/jm058057p

  日期：2006.4.1

  The 3-ethoxycarbonyl-4-quinolone compound I has previously been identified via a database search as an interesting lead compound for ligand binding at the benzodiazepine site of GABA(A) receptors (Kahnberg et al. J. Mol. Graphics Modelling 2004, 23, 253-261). Pharmacophore-guided optimization of this lead compound yielded a number of high-affinity ligands for the benzodiazepine site including compounds 20 and 23-25 displaying sub-nanomolar affinities. A few of the compounds have been tested on the alpha(1)beta(2)gamma(2s) and alpha(3)beta(2)gamma(2s) GABA(A) receptor subtypes, and two of the compounds (5 and 19) display selectivity for alpha(1) versus alpha(3)-containing receptors by a factor of 22 and 27, respectively. This selectivity for alpha(1)beta(2)gamma(2s) is in the same range as that for the well-known alpha(1) subunit selective compound zolpidem.