N-(6-acetyl-3-methoxy-2-methylphenyl)-4-cyclopropylthiazole-2-carboxamide | 1237745-86-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(6-acetyl-3-methoxy-2-methylphenyl)-4-cyclopropylthiazole-2-carboxamide
• 英文别名: N-(6-acetyl-3-methoxy-2-methylphenyl)-4-cyclopropyl-1,3-thiazole-2-carboxamide
• CAS: 1237745-86-6
• 化学式: C₁₇H₁₈N₂O₃S
• 分子量: 330.408
• InChiKey: CQUCBLXEOKVEIO-UHFFFAOYSA-N

物化性质

• 密度：
  1.317±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  96.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(6-acetyl-3-methoxy-2-methylphenyl)-4-cyclopropylthiazole-2-carboxamide 在 吡啶 、 盐酸 、 potassium tert-butylate 、 sodium hydride 、 三乙胺 、 potassium hydroxide 、 三氯氧磷 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， 反应 7.0h， 生成
  参考文献：
  名称：

  Synthesis and antiviral activity of novel HCV NS3 protease inhibitors with P4 capping groups

  摘要：

  We have synthesized and evaluated a series of novel HCV NS3 protease inhibitors with various P4 capping groups, which include urea, carbamate, methoxy-carboxamide, cyclic carbamate and amide, pyruvic amide, oxamate, oxalamide and cyanoguanidine. Most of these compounds are remarkably potent, exhibiting single-digit to sub-nanomolar activity in the enzyme assay and cell-based replicon assay. Selected compounds were also evaluated in the protease-inhibitor-resistant mutant transient replicon assay, and they were found to show quite different potency profiles against a panel of HCV protease-inhibitor-resistant mutants. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.075
• 作为产物：
  描述：

  2-甲基-3-甲氧基苯胺 在 三氯化硼 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 二氯甲烷 、 对二甲苯 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.08h， 生成 N-(6-acetyl-3-methoxy-2-methylphenyl)-4-cyclopropylthiazole-2-carboxamide
  参考文献：
  名称：

  Discovery of Novel Urea-Based Hepatitis C Protease Inhibitors with High Potency against Protease-Inhibitor-Resistant Mutants

  摘要：

  The macrocyclic urea 2, a byproduct in the synthesis of benzoxaborole 1, was identified to be a novel and potent HCV protease inhibitor. We further explored this motif by synthesizing additional urea-based inhibitors and by characterizing them in replicase HCV protease-resistant mutants assay. Several compounds, exemplified by 12, were found to be more potent in HCV replicon assays than leading second generation inhibitors such as danoprevir and TMC-435350. Additionally, following oral administration, inhibitor 12 was found in rat liver in significantly higher concentrations than those reported for both danoprevir and TMC-435350, suggesting that inhibitor 12 has the combination of anti-HCV and pharmacokinetic properties that warrants further development of this series.

  DOI：

  10.1021/jm201278q

文献信息

• COMPOUNDS
  申请人：COOPER JOEL

  公开号：US20100196321A1

  公开（公告）日：2010-08-05

  The present invention features compounds of Formula (I) and (Ia), pharmaceutical compositions and use in the treatment of viral disease:

  这项发明涉及Formula (I)和(Ia)的化合物，药物组合物以及在治疗病毒性疾病中的应用。
• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：GLAXOSMITHKLINE LLC

  公开号：WO2010088394A1

  公开（公告）日：2010-08-05

  The present invention features compounds of Formula (I) and (Ia), pharmaceutical compositions and use in the treatment of viral disease.
• [EN] HCV INHIBITOR COMPOUNDS AND METHODS OF USE THEREOF<br/>[FR] COMPOSÉS INHIBITEURS DU VIRUS DE L'HÉPATITE C (HCV) ET LEURS PROCÉDÉS D'UTILISATION
  申请人：ANACOR PHARMACEUTICALS INC

  公开号：WO2011150190A2

  公开（公告）日：2011-12-01

  The present invention features compounds of Formula (I), (II) and (III), pharmaceutical compositions and use in the treatment of viral disease: