{(S)-1-[2-(4-Methoxy-phenylamino)-ethylcarbamoyl]-3-methyl-butyl}-carbamic acid benzyl ester | 289043-10-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: {(S)-1-[2-(4-Methoxy-phenylamino)-ethylcarbamoyl]-3-methyl-butyl}-carbamic acid benzyl ester
• 英文别名: benzyl N-[(2S)-1-[2-(4-methoxyanilino)ethylamino]-4-methyl-1-oxopentan-2-yl]carbamate
• CAS: 289043-10-3
• 化学式: C₂₃H₃₁N₃O₄
• 分子量: 413.517
• InChiKey: FABDEVCIFFZYAX-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  88.7
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  {(S)-1-[2-(4-Methoxy-phenylamino)-ethylcarbamoyl]-3-methyl-butyl}-carbamic acid benzyl ester 在 10percent Pd/C 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 1-(2-chlorophenyl)-N-[(2S)-1-[2-(4-methoxyanilino)ethylamino]-4-methyl-1-oxopentan-2-yl]-1,2,4-triazole-3-carboxamide
  参考文献：
  名称：

  Arylaminoethyl Amides as Novel Non-Covalent Cathepsin K Inhibitors

  摘要：

  A series of N-alpha-benzyloxycarbonyl- and N-alpha-acyl-L-leucine(2-phenylaminoethyl)amide derivatives were prepared and evaluated for their inhibitory activity against rabbit and human cysteine proteases cathepsins K, L, and S. These data indicate that N-alpha-acyl-alpha-amino acid-(arylaminoethyl)amides represent a new class of selective non-covalent inhibitors of cathepsin K. Compounds 4b, 4e, and 4g exhibit high potency toward rabbit and human cathepsin K (IC50 < 0.006 muM) and are characterized by an excellent selectivity profile vs human cathepsins L and S.

  DOI：

  10.1021/jm010801s
• 作为产物：
  描述：

  对茴香胺盐酸盐 在 N,N-二异丙基乙胺 作用下， 以 乙二醇二甲醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 生成 {(S)-1-[2-(4-Methoxy-phenylamino)-ethylcarbamoyl]-3-methyl-butyl}-carbamic acid benzyl ester
  参考文献：
  名称：

  Arylaminoethyl Amides as Novel Non-Covalent Cathepsin K Inhibitors

  摘要：

  A series of N-alpha-benzyloxycarbonyl- and N-alpha-acyl-L-leucine(2-phenylaminoethyl)amide derivatives were prepared and evaluated for their inhibitory activity against rabbit and human cysteine proteases cathepsins K, L, and S. These data indicate that N-alpha-acyl-alpha-amino acid-(arylaminoethyl)amides represent a new class of selective non-covalent inhibitors of cathepsin K. Compounds 4b, 4e, and 4g exhibit high potency toward rabbit and human cathepsin K (IC50 < 0.006 muM) and are characterized by an excellent selectivity profile vs human cathepsins L and S.

  DOI：

  10.1021/jm010801s

文献信息

• Arylaminoethyl amides as inhibitors of the cysteine protease cathepsin K—investigating P1′ substituents
  作者：Eva Altmann、Jonathan Green、Marina Tintelnot-Blomley

  DOI：10.1016/s0960-894x(03)00344-5

  日期：2003.6

  Modeling, synthesis and in vitro activities of a series of arylaminoethyl amide based inhibitors of the cysteine protease cathepsin K are described. (C) 2003 Elsevier Science Ltd. All rights reserved.