2-[4-(Tert-butoxycarbonylamino)-3-thienyl]-5,6-dihydroxy-pyrimidine-4-carboxylic acid | 1102363-35-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-[4-(Tert-butoxycarbonylamino)-3-thienyl]-5,6-dihydroxy-pyrimidine-4-carboxylic acid
• 英文别名: 5-hydroxy-2-[4-[(2-methylpropan-2-yl)oxycarbonylamino]thiophen-3-yl]-6-oxo-1H-pyrimidine-4-carboxylic acid
• CAS: 1102363-35-8
• 化学式: C₁₄H₁₅N₃O₆S
• 分子量: 353.356
• InChiKey: HMJXOWDKKNFHTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  24
• 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：
  166
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  methyl 2-(3-tert-butyloxycarbonylamino-4 thienyl)-4,5-dihydroxypyrimidine-6-carboxylate 在 lithium hydrochloride monohydrate 、 水 作用下， 以 四氢呋喃 为溶剂， 生成 2-[4-(Tert-butoxycarbonylamino)-3-thienyl]-5,6-dihydroxy-pyrimidine-4-carboxylic acid
  参考文献：
  名称：

  2-(3-Thienyl)-5,6-dihydroxypyrimidine-4-carboxylic acids as inhibitors of HCV NS5B RdRp

  摘要：

  A series of 2-(3-thienyl)-5,6-dihydroxypyrimidine-4-carboxylic acid inhibitors of the hepatitis C virus (HCV) NS5B polymerase enzyme are reported. Sulfonyl urea substituted analogs in this series proved to be the most potent active site non-nucleoside inhibitors of NS5B reported to date. These compounds had low nanomolar enzyme inhibition across HCV genotypes 1-3 and showed single digit micromolar inhibition in the HCV replicon assay. This improved cell-based activity allowed the binding mode of these compounds to be probed by selection of resistant mutations against compound 21. The results generated are in broad agreement with the previously proposed binding model for this compound class. (C) 2009 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2009.06.106

文献信息

• 2-(3-Thienyl)-5,6-dihydroxypyrimidine-4-carboxylic acids as inhibitors of HCV NS5B RdRp
  作者：Barbara Pacini、Salvatore Avolio、Caterina Ercolani、Uwe Koch、Giovanni Migliaccio、Frank Narjes、Laura Pacini、Licia Tomei、Steven Harper

  DOI：10.1016/j.bmcl.2009.06.106

  日期：2009.11

  A series of 2-(3-thienyl)-5,6-dihydroxypyrimidine-4-carboxylic acid inhibitors of the hepatitis C virus (HCV) NS5B polymerase enzyme are reported. Sulfonyl urea substituted analogs in this series proved to be the most potent active site non-nucleoside inhibitors of NS5B reported to date. These compounds had low nanomolar enzyme inhibition across HCV genotypes 1-3 and showed single digit micromolar inhibition in the HCV replicon assay. This improved cell-based activity allowed the binding mode of these compounds to be probed by selection of resistant mutations against compound 21. The results generated are in broad agreement with the previously proposed binding model for this compound class. (C) 2009 Published by Elsevier Ltd.