1-(3-hydroxypropyl)-6-(benzo[b]furan-2-yl)-4-oxoquinoline-3-carboxylic acid | 1393355-14-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: 1-(3-hydroxypropyl)-6-(benzo[b]furan-2-yl)-4-oxoquinoline-3-carboxylic acid
• 英文别名: 6-(Benzofuran-2-yl)-1-(3-hydroxypropyl)-4-oxo-quinoline-3-carboxylic acid；6-(1-benzofuran-2-yl)-1-(3-hydroxypropyl)-4-oxoquinoline-3-carboxylic acid
• CAS: 1393355-14-0
• 化学式: C₂₁H₁₇NO₅
• 分子量: 363.37
• InChiKey: UVJCUWQMPXLZNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  91
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  6-碘-4-氧代-1,4-二氢喹啉-3-羧酸乙酯 在 水 、 potassium carbonate 、 对甲苯磺酸 、 palladium dichloride 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.44h， 生成 1-(3-hydroxypropyl)-6-(benzo[b]furan-2-yl)-4-oxoquinoline-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

文献信息

• C-6 aryl substituted 4-quinolone-3-carboxylic acids as inhibitors of hepatitis C virus
  作者：Yue-Lei Chen、Jeana Zacharias、Robert Vince、Robert J. Geraghty、Zhengqiang Wang

  DOI：10.1016/j.bmc.2012.05.066

  日期：2012.8

  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.