1-(2-(methylamino)-2-oxoethyl)-1H-pyrazole-3-carboxylic acid | 1006463-30-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2-(methylamino)-2-oxoethyl)-1H-pyrazole-3-carboxylic acid
• 英文别名: 1-[(methylcarbamoyl)methyl]-1H-pyrazole-3-carboxylic acid；1-[2-(methylamino)-2-oxoethyl]pyrazole-3-carboxylic acid
• CAS: 1006463-30-4
• 化学式: C₇H₉N₃O₃
• 分子量: 183.167
• InChiKey: UOQLXPIMXMUNJO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  84.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-chloro-4-(trans-3-amino-2,2,4,4-tetramethylcyclobutoxy)benzonitrile 、 1-(2-(methylamino)-2-oxoethyl)-1H-pyrazole-3-carboxylic acid 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 生成 N,N-[trans-3-(3-chloro-4-cyanophenoxy)-2,2,4,4-tetramethylcyclobutyl]-1-[ 2-(methylamino)-2-oxoethyl]-1H-pyrazole-3-carboxamide
  参考文献：
  名称：

  Discovery of Aryloxy Tetramethylcyclobutanes as Novel Androgen Receptor Antagonists

  摘要：

  An aryloxy tetramethylcyclobutane was identified as a novel template for androgen receptor (AR) antagonists via cell-based high-throughput screening. Follow-up to the initial "hit" established 5 as a viable lead. Further optimization to achieve full AR antagonism led to the discovery of 26 and 30, both of which demonstrated excellent in vivo tumor growth inhibition upon oral administration in a castration-resistant prostate cancer (CRPC) animal model.

  DOI：

  10.1021/jm201059s

文献信息

• [EN] HEPATITIS C INHIBITOR COMPOUNDS<br/>[FR] COMPOSÉS INHIBITEURS DE L'HÉPATITE C
  申请人：BOEHRINGER INGELHEIM INT

  公开号：WO2011063501A1

  公开（公告）日：2011-06-03

  Compounds of the invention, which are macrocyclic peptide analogs containing an acylsulfonamide moiety, maintain good activity against NS3 proteases containing clinically relevant resistance mutations for this class as represented by genotype 1 a R155K, genotype 1 b D168V and genotype 1 a D168V resistance mutations. The compounds of the invention are useful as inhibitors of HCV NS3 protease for the treatment of hepatitis C viral infection.

  本发明的化合物是含有酰磺酰胺基团的大环肽类似物，对包含临床相关耐药突变的NS3蛋白酶保持良好的活性，这些耐药突变由基因型1a的R155K、基因型1b的D168V和基因型1a的D168V耐药突变代表。本发明的化合物可用作HCV 蛋白酶的抑制剂，用于治疗丙型肝炎病毒感染。
• HEPATITIS C INHIBITOR COMPOUNDS
  申请人：Llinas-Brunet Montse

  公开号：US20120077737A1

  公开（公告）日：2012-03-29

  Compounds of the invention, which are macrocyclic peptide analogs containing an acylsulfonamide moiety, maintain good activity against NS3 proteases containing clinically relevant resistance mutations for this class as represented by genotype 1a R155K, genotype 1b D168V and genotype 1a D168V resistance mutations. The compounds of the invention are useful as inhibitors of HCV NS3 protease for the treatment of hepatitis C viral infection.

  本发明的化合物是含有酰基磺酰胺基团的大环肽类似物，在对于该类别的NS3蛋白酶含有临床相关的耐药突变，如基因型1a R155K、基因型1b D168V和基因型1a D168V耐药突变时，仍然保持良好的活性。本发明的化合物可用作HCV 蛋白酶的抑制剂，用于治疗丙型肝炎病毒感染。