ethyl 6-iodo-4-oxo-1-propyl-1,4-dihydro-3-quinolinecarboxylate | 936624-98-5

• 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 6-iodo-4-oxo-1-propyl-1,4-dihydro-3-quinolinecarboxylate
• 英文别名: ethyl 6-iodo-4-oxo-1-propylquinoline-3-carboxylate
• CAS: 936624-98-5
• 化学式: C₁₅H₁₆INO₃
• 分子量: 385.201
• InChiKey: SOZCJNRDTKZFND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 6-iodo-4-oxo-1-propyl-1,4-dihydro-3-quinolinecarboxylate 在 水 、 potassium carbonate 、 palladium dichloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.16h， 生成 1-n-propyl-6-(benzo[b]furan-2-yl)-4-oxo-quinoline-3-carboxylic acid
  参考文献：
  名称：

  C-6 aryl substituted 4-quinolone-3-carboxylic acids as inhibitors of hepatitis C virus

  摘要：

  Quinolone-3-carboxylic acid represents a highly privileged chemotype in medicinal chemistry and has been extensively explored as antibiotics and antivirals targeting human immunodeficiency virus (HIV) integrase (IN). Herein we describe the synthesis and anti-hepatitis C virus (HCV) profile of a series of C-6 aryl substituted 4-quinlone-3-carboxylic acid analogues. Significant inhibition was observed with a few analogues at low micromolar range against HCV replicon in cell culture and a reduction in replicon RNA was confirmed through an RT-qPCR assay. Interestingly, evaluation of analogues as inhibitors of NS5B in a biochemical assay yielded only modest inhibitory activities, suggesting that a different mechanism of action could operate in cell culture. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.066
• 作为产物：
  描述：

  乙氧基甲叉丙二酸二乙酯 在 potassium carbonate 作用下， 以 二苯醚 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.78h， 生成 ethyl 6-iodo-4-oxo-1-propyl-1,4-dihydro-3-quinolinecarboxylate
  参考文献：
  名称：

  C-6 aryl substituted 4-quinolone-3-carboxylic acids as inhibitors of hepatitis C virus

  摘要：

  Quinolone-3-carboxylic acid represents a highly privileged chemotype in medicinal chemistry and has been extensively explored as antibiotics and antivirals targeting human immunodeficiency virus (HIV) integrase (IN). Herein we describe the synthesis and anti-hepatitis C virus (HCV) profile of a series of C-6 aryl substituted 4-quinlone-3-carboxylic acid analogues. Significant inhibition was observed with a few analogues at low micromolar range against HCV replicon in cell culture and a reduction in replicon RNA was confirmed through an RT-qPCR assay. Interestingly, evaluation of analogues as inhibitors of NS5B in a biochemical assay yielded only modest inhibitory activities, suggesting that a different mechanism of action could operate in cell culture. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.066

文献信息

• MACROLONES
  申请人：Alihodzic Sulejman

  公开号：US20090170791A1

  公开（公告）日：2009-07-02

  A compound of formula (I) or a pharmaceutically acceptable derivative thereof, having antimicrobial activity, processes for their preparation, compositions containing them and to their use in medicine.

  具有抗微生物活性的化合物式（I）或其药学上可接受的衍生物，制备它们的方法，包含它们的组合物以及它们在医学上的使用。
• WO2007/54296
  申请人：——

  公开号：——

  公开（公告）日：——
• [EN] MACROLONES<br/>[FR] MACROLONES
  申请人：GLAXO GROUP LTD

  公开号：WO2007054296A1

  公开（公告）日：2007-05-18

  [EN] A compound of formula (I) or a pharmaceutically acceptable derivative thereof, having antimicrobial activity, processes for their preparation, compositions containing them and to their use in medicine.
  [FR] L'invention concerne un composé de formule (I) ou un dérivé pharmaceutiquement acceptable de ce composé ayant une activité antimicrobienne, des procédés de fabrication des macrolones, des compositions les contenant et leur utilisation en médecine.