Ethyl 6-(methylamino)-5-nitro-1-benzothiophene-2-carboxylate | 926648-22-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: Ethyl 6-(methylamino)-5-nitro-1-benzothiophene-2-carboxylate
• CAS: 926648-22-8
• 化学式: C₁₂H₁₂N₂O₄S
• 分子量: 280.304
• InChiKey: VQNFZDSIOFBASY-UHFFFAOYSA-N

物化性质

• 沸点：
  462.2±45.0 °C(Predicted)
• 密度：
  1.410±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ethyl 6-(methylamino)-5-nitro-1-benzothiophene-2-carboxylate 在 吡啶 、 溶剂黄146 、 tin(ll) chloride 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Conformation-Based Restrictions and Scaffold Replacements in the Design of Hepatitis C Virus Polymerase Inhibitors: Discovery of Deleobuvir (BI 207127)

  摘要：

  Conformational restrictions of flexible torsion angles were used to guide the identification of new chemotypes of HCV NS5B inhibitors. Sites for rigidification were based on an acquired conformational understanding of compound binding requirements and the roles of substituents in the free and bound states. Chemical bioisosteres of amide bonds were explored to improve cell-based potency. Examples are shown, including the design concept that led to the discovery of the phase III clinical candidate deleobuvir (BI 207127). The structure-based strategies employed have general utility in drug design.

  DOI：

  10.1021/jm4011862
• 作为产物：
  描述：

  2,4-二氟-5-硝基苯甲酸 在 盐酸 、 二异丁基氢化铝 、 戴斯-马丁氧化剂 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 Ethyl 6-(methylamino)-5-nitro-1-benzothiophene-2-carboxylate
  参考文献：
  名称：

  Conformation-Based Restrictions and Scaffold Replacements in the Design of Hepatitis C Virus Polymerase Inhibitors: Discovery of Deleobuvir (BI 207127)

  摘要：

  Conformational restrictions of flexible torsion angles were used to guide the identification of new chemotypes of HCV NS5B inhibitors. Sites for rigidification were based on an acquired conformational understanding of compound binding requirements and the roles of substituents in the free and bound states. Chemical bioisosteres of amide bonds were explored to improve cell-based potency. Examples are shown, including the design concept that led to the discovery of the phase III clinical candidate deleobuvir (BI 207127). The structure-based strategies employed have general utility in drug design.

  DOI：

  10.1021/jm4011862

文献信息

• WO2007/19674
  申请人：——

  公开号：——

  公开（公告）日：——
• Viral Polymerase Inhibitors
  申请人：Tsantrizos Youla S.

  公开号：US20100168098A1

  公开（公告）日：2010-07-01

  The present invention relates to compounds represented by formula (I) wherein A, B, D, E, R 2 , R 3 , R 4 , R 5 , R 6 , R 9 , a, b, d and e are as defined herein, their salt or ester and pharmaceutical compositions thereof useful in the treatment of hepatitis C viral (HCV) infection. Said compounds were found to have inhibitory activity against HCV polymerase, especially as inhibitors of HCV NS5B polymerase
• US8076365B2
  申请人：——

  公开号：US8076365B2

  公开（公告）日：2011-12-13
• [EN] VIRAL POLYMERASE INHIBITORS<br/>[FR] INHIBITEURS DE POLYMERASE VIRALE
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2007019674A1

  公开（公告）日：2007-02-22

  [EN] The present invention relates to compounds represented by formula (I) wherein A, B, D, E, R², R³, R⁴, R⁵, R⁶, R⁹, a, b, d and e are as defined herein, their salt or ester and pharmaceutical compositions thereof useful in the treatment of hepatitis C viral (HCV) infection. Said compounds were found to have inhibitory activity against HCV polymerase, especially as inhibitors of HCV NS5B polymerase
  [FR] La présente invention concerne des composés de formule (I) où A, B, D, E, R², R³, R⁴, R⁵, R⁶, R⁹, a, b, d et e sont tels que définis dans la description, leur sel ou ester, ainsi que des préparations pharmaceutiques incluant ces composés et pouvant être employées dans le traitement d'une infection par le virus de l'hépatite C (VHC). Il a été découvert que lesdits composés présentaient une activité inhibitrice vis-à-vis de la polymérase du VHC, en particulier vis-à-vis de la polymérase NS5B du VHC.
• Conformation-Based Restrictions and Scaffold Replacements in the Design of Hepatitis C Virus Polymerase Inhibitors: Discovery of Deleobuvir (BI 207127)
  作者：Steven R. LaPlante、Michael Bös、Christian Brochu、Catherine Chabot、René Coulombe、James R. Gillard、Araz Jakalian、Martin Poirier、Jean Rancourt、Timothy Stammers、Bounkham Thavonekham、Pierre L. Beaulieu、George Kukolj、Youla S. Tsantrizos

  DOI：10.1021/jm4011862

  日期：2014.3.13

  Conformational restrictions of flexible torsion angles were used to guide the identification of new chemotypes of HCV NS5B inhibitors. Sites for rigidification were based on an acquired conformational understanding of compound binding requirements and the roles of substituents in the free and bound states. Chemical bioisosteres of amide bonds were explored to improve cell-based potency. Examples are shown, including the design concept that led to the discovery of the phase III clinical candidate deleobuvir (BI 207127). The structure-based strategies employed have general utility in drug design.