2-acetyl-8-(cyclohexyloxy)-1-oxo-1H-pyrido[2,1-b][1,3]benzothiazole-4-carboxylic acid | 1355361-76-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻唑类
• 英文名称: 2-acetyl-8-(cyclohexyloxy)-1-oxo-1H-pyrido[2,1-b][1,3]benzothiazole-4-carboxylic acid
• 英文别名: 2-Acetyl-8-(cyclohexoxy)-1-oxo-pyrido[2,1-b][1,3]benzothiazole-4-carboxylic acid；2-acetyl-8-cyclohexyloxy-1-oxopyrido[2,1-b][1,3]benzothiazole-4-carboxylic acid
• CAS: 1355361-76-0
• 化学式: C₂₀H₁₉NO₅S
• 分子量: 385.441
• InChiKey: VOWXNIGPFPITEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  109
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-甲基-5-苯并噻唑 在 lithium hydroxide monohydrate 、 水 、 三乙胺 、 三苯基膦 、 sodium hydroxide 、 偶氮二甲酸二乙酯 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 乙二醇 为溶剂， 反应 190.0h， 生成 2-acetyl-8-(cyclohexyloxy)-1-oxo-1H-pyrido[2,1-b][1,3]benzothiazole-4-carboxylic acid
  参考文献：
  名称：

  Pyridobenzothiazole derivatives as new chemotype targeting the HCV NS5B polymerase

  摘要：

  Hepatitis C virus (HCV) infection has been recognized as the major cause of liver failure that can lead to hepatocellular carcinoma. Among all the HCV proteins, NS5B polymerase represents a leading target for drug discovery strategies. Herein, we describe our initial research efforts towards the identification of new chemotypes as allosteric NS5B inhibitors. In particular, the design, synthesis, in vitro anti-NS5B and in cellulo anti-HCV evaluation of a series of 1-oxo-1H-pyrido[2,1-b][1,3]benzothiazole-4-carboxylate derivatives are reported. Some of the newly synthesized compounds showed an IC50 ranging from 11 to 23 mu M, and molecular modeling and biochemical studies suggested that the thumb domain could be the target site for this new class of NS5B inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.061

文献信息

• Pyridobenzothiazole derivatives as new chemotype targeting the HCV NS5B polymerase
  作者：Giuseppe Manfroni、Francesco Meschini、Maria Letizia Barreca、Pieter Leyssen、Alberta Samuele、Nunzio Iraci、Stefano Sabatini、Serena Massari、Giovanni Maga、Johan Neyts、Violetta Cecchetti

  DOI：10.1016/j.bmc.2011.11.061

  日期：2012.1

  Hepatitis C virus (HCV) infection has been recognized as the major cause of liver failure that can lead to hepatocellular carcinoma. Among all the HCV proteins, NS5B polymerase represents a leading target for drug discovery strategies. Herein, we describe our initial research efforts towards the identification of new chemotypes as allosteric NS5B inhibitors. In particular, the design, synthesis, in vitro anti-NS5B and in cellulo anti-HCV evaluation of a series of 1-oxo-1H-pyrido[2,1-b][1,3]benzothiazole-4-carboxylate derivatives are reported. Some of the newly synthesized compounds showed an IC50 ranging from 11 to 23 mu M, and molecular modeling and biochemical studies suggested that the thumb domain could be the target site for this new class of NS5B inhibitors. (C) 2011 Elsevier Ltd. All rights reserved.