1-phenyl-7,7-dimethyl-2,5-dioxo-1,2,5,6,7,8-hexahydro-3-quinolinecarboxamide | 354146-74-0

• 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
• 英文名称: 1-phenyl-7,7-dimethyl-2,5-dioxo-1,2,5,6,7,8-hexahydro-3-quinolinecarboxamide
• 英文别名: 7,7-Dimethyl-2,5-dioxo-1-phenyl-6,8-dihydroquinoline-3-carboxamide
• CAS: 354146-74-0
• 化学式: C₁₈H₁₈N₂O₃
• 分子量: 310.353
• InChiKey: GSXOASLNXMYUTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  80.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  dimethylammonium 2-(2-carbamoyl-2-cyano-1-ethenyl)-5,5-dimethyl-3-oxo-1-cyclohexen-1-olate 、 苯胺 在 溶剂黄146 作用下， 以74%的产率得到1-phenyl-7,7-dimethyl-2,5-dioxo-1,2,5,6,7,8-hexahydro-3-quinolinecarboxamide
  参考文献：
  名称：

  An efficient synthesis of N1-substituted 2,5-dioxo-1,2,5,6,7,8-hexahydro-3-quinolinecarboxamide via enolate salts

  摘要：

  Various 2-(2-cyano-2-carbamoyl-1-ethenyl)-5,5-dimethyl-3-oxo-1-cyclohexen-1-olates substituted in the amide group with dialkylammonium or sodium cations were prepared via reactions of N-substituted cyanoacetamides with dimedone-DMFDMA adduct by a one-pot, two-step protocol. The salts obtained were used in reactions with N-nucleophiles for further synthesis of the N1-substituted 2,5-dioxo- 1,2,5,6,7,8-hexahydro-3-quinolinecarboxamides that are analogues of well-known pharmaceuticals. The structure of the salts and the N1-substituted 2,5-dioxo-1,2,5,6,7,8-hexahydro-3-quinolinecarboxamides was established by means of spectroscopic and X-ray diffraction studies. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.02.095

文献信息

• QUINOLINE DERIVATIVE
  申请人：ONO PHARMACEUTICAL CO., LTD.

  公开号：US20160168121A1

  公开（公告）日：2016-06-16

  A compound represented by general formula (I) has a strong Axl inhibitory activity by introducing a distinctive bicyclic structure in which a saturated carbon ring is fused to a pyridone ring, and can be a therapeutic agent for Axl-related diseases, for example, cancer such as acute myeloid leukemia, melanoma, breast cancer, pancreatic cancer, and glioma, kidney diseases, immune system diseases, and circulatory system diseases.

  通式（I）所代表的化合物通过引入一种独特的双环结构，在其中饱和碳环与吡啶酮环融合，具有强烈的Axl抑制活性，并可作为Axl相关疾病的治疗剂，例如急性髓性白血病、黑色素瘤、乳腺癌、胰腺癌和胶质瘤、肾脏疾病、免疫系统疾病和循环系统疾病的治疗剂。
• US9573935B2
  申请人：——

  公开号：US9573935B2

  公开（公告）日：2017-02-21
• An efficient synthesis of N1-substituted 2,5-dioxo-1,2,5,6,7,8-hexahydro-3-quinolinecarboxamide via enolate salts
  作者：Sergey A. Yermolayev、Nikolay Yu. Gorobets、Elena V. Lukinova、Oleg V. Shishkin、Svetlana V. Shishkina、Sergey M. Desenko

  DOI：10.1016/j.tet.2008.02.095

  日期：2008.5

  Various 2-(2-cyano-2-carbamoyl-1-ethenyl)-5,5-dimethyl-3-oxo-1-cyclohexen-1-olates substituted in the amide group with dialkylammonium or sodium cations were prepared via reactions of N-substituted cyanoacetamides with dimedone-DMFDMA adduct by a one-pot, two-step protocol. The salts obtained were used in reactions with N-nucleophiles for further synthesis of the N1-substituted 2,5-dioxo- 1,2,5,6,7,8-hexahydro-3-quinolinecarboxamides that are analogues of well-known pharmaceuticals. The structure of the salts and the N1-substituted 2,5-dioxo-1,2,5,6,7,8-hexahydro-3-quinolinecarboxamides was established by means of spectroscopic and X-ray diffraction studies. (C) 2008 Elsevier Ltd. All rights reserved.