ethyl 7,8-dimethoxy-4-oxo-1,4-dihydroquinolin-3-carboxylate | 26893-07-2

• 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: ethyl 7,8-dimethoxy-4-oxo-1,4-dihydroquinolin-3-carboxylate
• 英文别名: ethyl 7,8-dimethoxy-4-quinolone-3-carboxylate；Ethyl 4-hydroxy-7,8-dimethoxyquinoline-3-carboxylate；ethyl 7,8-dimethoxy-4-oxo-1H-quinoline-3-carboxylate
• CAS: 26893-07-2
• 化学式: C₁₄H₁₅NO₅
• 分子量: 277.277
• InChiKey: MMSQYVSVWYZUKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 7,8-dimethoxy-4-oxo-1,4-dihydroquinolin-3-carboxylate 在 manganese(IV) oxide 、 三溴化硼 、 potassium carbonate 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 45.0h， 生成 1-ethyl-7,8-bis((4-methoxybenzyl)oxy)-4-oxo-1,4-dihydroquinoline-3-carbaldehyde
  参考文献：
  名称：

  [EN] ANTIBACTERIAL COMPOUNDS
  [FR] COMPOSÉS ANTIBACTÉRIENS

  摘要：

  本发明涉及头孢菌素抗菌化合物的公式（I）：以及相应的药学上可接受的盐、相应的药物组合物、化合物制备和治疗细菌感染的方法，特别是由革兰氏阴性细菌引起的感染。

  公开号：

  WO2013052568A1
• 作为产物：
  描述：

  2,3-二甲氧基苯胺 以 乙醇 为溶剂， 反应 2.0h， 生成 ethyl 7,8-dimethoxy-4-oxo-1,4-dihydroquinolin-3-carboxylate
  参考文献：
  名称：

  [EN] ANTIBACTERIAL COMPOUNDS
  [FR] COMPOSÉS ANTIBACTÉRIENS

  摘要：

  本发明涉及头孢菌素抗菌化合物的公式（I）：以及相应的药学上可接受的盐、相应的药物组合物、化合物制备和治疗细菌感染的方法，特别是由革兰氏阴性细菌引起的感染。

  公开号：

  WO2013052568A1

文献信息

• ANTIBACTERIAL COMPOUNDS
  申请人：GLAXO GROUP LIMITED

  公开号：US20140249126A1

  公开（公告）日：2014-09-04

  The present invention relates to cephalosporin antibacterial compounds of Formula (I): or corresponding pharmaceutically acceptable salts thereof, corresponding pharmaceutical compositions, compound preparation and treatment methods for bacterial infections, especially those caused by gram-negative bacteria.

  本发明涉及式（I）的头孢菌素抗菌化合物：或其相应的药学上可接受的盐，相应的制药组合物，化合物制备和治疗细菌感染的方法，特别是由革兰氏阴性菌引起的感染。
• Antibacterial compounds
  申请人：GLAXO GROUP LIMITED

  公开号：US09340556B2

  公开（公告）日：2016-05-17

  The present invention relates to cephalosporin antibacterial compounds of Formula (I): or corresponding pharmaceutically acceptable salts thereof, corresponding pharmaceutical compositions, compound preparation and treatment methods for bacterial infections, especially those caused by gram-negative bacteria.

  本发明涉及公式(I)的头孢菌素抗菌化合物，或其相应的药学上可接受的盐，相应的药物组成，化合物制备和治疗细菌感染的方法，尤其是由革兰氏阴性菌引起的感染。
• Structural development of a type-1 ryanodine receptor (RyR1) Ca2+-release channel inhibitor guided by endoplasmic reticulum Ca2+ assay
  作者：Shuichi Mori、Hiroto Iinuma、Noriaki Manaka、Mari Ishigami-Yuasa、Takashi Murayama、Yoshiaki Nishijima、Akiko Sakurai、Ryota Arai、Nagomi Kurebayashi、Takashi Sakurai、Hiroyuki Kagechika

  DOI：10.1016/j.ejmech.2019.06.076

  日期：2019.10

  Type-1 ryanodine receptor (RyRI) is a calcium-release channel localized on sarcoplasmic reticulum (SR) of the skeletal muscle, and mediates muscle contraction by releasing Ca2+ from the SR. Genetic mutations of RyRI are associated with skeletal muscle diseases such as malignant hyperthermia and central core diseases, in which over-activation of RyRI causes leakage of Ca2+ from the SR. We recently developed an efficient high-throughput screening system based on the measurement of Ca2+ in endoplasmic reticulum, and used it to identify oxolinic acid (1) as a novel RyRI channel inhibitor. Here, we designed and synthesized a series of quinolone derivatives based on 1 as a lead compound. Derivatives bearing a long alkyl chain at the nitrogen atom of the quinolone ring and having a suitable substituent at the 7-position of quinolone exhibited potent RyR1 channel-inhibitory activity. Among the synthesized compounds, 14h showed more potent activity than dantrolene, a known RyR1 inhibitor, and exhibited high RyR1 selectivity over RyR2 and RyR3. These compounds may be promising leads for clinically applicable RyRI channel inhibitors. (C) 2019 Elsevier Masson SAS. All rights reserved.
• US9340556B2
  申请人：——

  公开号：US9340556B2

  公开（公告）日：2016-05-17