tert-Butyl {4-[amino(hydroxyimino)methyl]thien-3-yl}carbamate | 391680-99-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 杂芳族化合物
• 英文名称: tert-Butyl {4-[amino(hydroxyimino)methyl]thien-3-yl}carbamate
• 英文别名: tert-butyl N-[4-(N'-hydroxycarbamimidoyl)thiophen-3-yl]carbamate
• CAS: 391680-99-2
• 化学式: C₁₀H₁₅N₃O₃S
• 分子量: 257.313
• InChiKey: ZCPZGKUJMOFDCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  125
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-Butyl {4-[amino(hydroxyimino)methyl]thien-3-yl}carbamate 、 丁炔二酸二甲酯 以 氯仿 、 对二甲苯 为溶剂， 生成 methyl 2-(3-tert-butyloxycarbonylamino-4 thienyl)-4,5-dihydroxypyrimidine-6-carboxylate
  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
• 作为产物：
  描述：

  3-tert-butyloxycarbonylamino-4-thiophene carbonitrile 在 盐酸羟胺 、 三乙胺 作用下， 以 甲醇 为溶剂， 生成 tert-Butyl {4-[amino(hydroxyimino)methyl]thien-3-yl}carbamate
  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

• Pyrimidinone viral polymerase inhibitors
  申请人：Avolio Salvatore

  公开号：US20050130997A1

  公开（公告）日：2005-06-16

  A class of pyrimidinone derivatives of formula (I): wherein Z, R 1 , R 2 and R 3 are as defined herein; and pharmaceutically acceptable salts thereof; are inhibitors of viral polymerases, especially (the hepatitis C virus (HCV) polymerase enzyme.

  一类嘧啶酮衍生物，其化学式为(I)：其中Z，R1，R2和R3如下定义；以及其药学上可接受的盐；是病毒聚合酶的抑制剂，特别是丙型肝炎病毒（HCV）聚合酶酶。
• 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.