ethyl 2-cyclohexyl-8-(cyclohexyloxy)-1-oxo-1H-pyrido[2,1-b][1,3]benzothiazole-4-carboxylate | 1355361-90-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并吡啶类
• 英文名称: ethyl 2-cyclohexyl-8-(cyclohexyloxy)-1-oxo-1H-pyrido[2,1-b][1,3]benzothiazole-4-carboxylate
• CAS: 1355361-90-8
• 化学式: C₂₆H₃₁NO₄S
• 分子量: 453.602
• InChiKey: TXQBAINESYROTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.45
• 重原子数：
  32.0
• 可旋转键数：
  5.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  57.01
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl 2-cyclohexyl-8-(cyclohexyloxy)-1-oxo-1H-pyrido[2,1-b][1,3]benzothiazole-4-carboxylate 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 2.0h， 以85%的产率得到2-cyclohexyl-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
• 作为产物：
  描述：

  5-(cyclohexyloxy)-2-methyl-1,3-benzothiazole 在 水 、 sodium hydroxide 、 三氯氧磷 作用下， 以 乙二醇 为溶剂， 反应 22.0h， 生成 ethyl 2-cyclohexyl-8-(cyclohexyloxy)-1-oxo-1H-pyrido[2,1-b][1,3]benzothiazole-4-carboxylate
  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