1,4-二氢-1,2-二甲基-4-氧代-3-喹啉羧酸 | 73281-83-1

• 物质功能分类: 天然产物 - 生物碱
• 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: 1,4-二氢-1,2-二甲基-4-氧代-3-喹啉羧酸
• 英文名称: 1,2-dimethyl-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid
• 英文别名: 1,4-Dihydro-1,2-dimethyl-4-oxo-3-quinolinecarboxylic acid；1,2-dimethyl-4-oxoquinoline-3-carboxylic acid
• CAS: 73281-83-1
• 化学式: C₁₂H₁₁NO₃
• 分子量: 217.224
• InChiKey: RDEXTEPFIVECBD-UHFFFAOYSA-N

物化性质

• 熔点：
  235 °C(Solv: ethanol (64-17-5))
• 沸点：
  352.7±42.0 °C(Predicted)
• 密度：
  1.313±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,4-二氢-1,2-二甲基-4-氧代-3-喹啉羧酸 在 氯化亚砜 作用下， 生成 3,3-dichloro-4-methyl-thieno[3,4-b]quinoline-1,9-dione
  参考文献：
  名称：

  Van Es, Theodorus; Staskun, Benjamin; Piggottd, Andrew M., South African Journal of Chemistry, 2006, vol. 59, p. 101 - 108

  摘要：

  DOI：
• 作为产物：
  描述：

  1,4-dihydro-1,2-dimethyl-4-oxoquinoline-3-carboxylic acid ethyl ester 、 sodium hydroxide 以85%的产率得到
  参考文献：
  名称：

  COPPOLA G. M.; HARDTMANN G. E., J. HETEROCYCL. CHEM., 1979, 16, NO 8, 1605-1610

  摘要：

  DOI：

文献信息

• 4-Oxo-1,4-dihydroquinoline-3-carboxamide Derivatives as New Axl Kinase Inhibitors
  作者：Li Tan、Zhang Zhang、Donglin Gao、Jinfeng Luo、Zheng-Chao Tu、Zhengqiu Li、Lijie Peng、Xiaomei Ren、Ke Ding

  DOI：10.1021/acs.jmedchem.6b00608

  日期：2016.7.28

  Axl is a new potential target for anticancer drug discovery. A series of 4-oxo-1,4-dihydroquinoline-3-carboxamides were designed and synthesized as highly potent Axl kinase inhibitors. One of the most promising compounds, 9im, tightly bound with Axl protein and potently inhibited its kinase function with a K-d value of 2.7 nM and an IC50 value of 4.0 nM, respectively, while was obviously less potent against most of the 403 wild-type kinases evaluated at a relatively high concentration. The compound dose-dependently inhibited the TGF-beta 1-induced epithelial-mesenchymal transition (EMT) and suppressed the migration and invasion of MDA-MB-231 breast cancer cells. In addition, 9im also demonstrated reasonable pharmacokinetics properties in rats and exhibited in vivo therapeutic effect on hepatic metastasis in a xenograft model of highly metastatic 4T1 murine breast cancer cells. Compound 9im may serve as a lead compound for new anticancer drug discovery and a valuable research probe for further biological investigation on Axl.