benzyl N-[(2S)-4-methyl-1-oxo-1-(phenacylamino)pentan-2-yl]carbamate | 167983-27-9

• 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: benzyl N-[(2S)-4-methyl-1-oxo-1-(phenacylamino)pentan-2-yl]carbamate
• CAS: 167983-27-9
• 化学式: C₂₂H₂₆N₂O₄
• 分子量: 382.459
• InChiKey: DWYAZLOEYPIWLO-IBGZPJMESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  84.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  benzyl N-[(2S)-4-methyl-1-oxo-1-(phenacylamino)pentan-2-yl]carbamate 在 palladium on activated charcoal ammonium acetate 、 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 8.0h， 生成 (1S)-3-methyl-1-(4-phenyl-1H-imidazol-2-yl)-1-butanamine
  参考文献：
  名称：

  Design, synthesis, activity, and structure of a novel class of matrix metalloproteinase inhibitors containing a heterocyclic P2′-P3′ amide bond isostere

  摘要：

  A novel series of hydroxamate-based inhibitors of matrix metalloproteinases containing benzimidazole and imidazole heterocycles as amide bond isosteres have been prepared. Potent inhibition (in the low nanomolar range) and selectivity (> 100-fold) can be attained with inhibitors containing only one amide bond. X-ray crystal structures of matrilysin (MMP-7) with two different inhibitors bound confirm that imidazole is an excellent amide bond isostere. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00283-1
• 作为产物：
  描述：

  N-苄氧羰基-L-亮氨酸 、 2-氨基苯乙酮 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 生成 benzyl N-[(2S)-4-methyl-1-oxo-1-(phenacylamino)pentan-2-yl]carbamate
  参考文献：
  名称：

  Design, synthesis, activity, and structure of a novel class of matrix metalloproteinase inhibitors containing a heterocyclic P2′-P3′ amide bond isostere

  摘要：

  A novel series of hydroxamate-based inhibitors of matrix metalloproteinases containing benzimidazole and imidazole heterocycles as amide bond isosteres have been prepared. Potent inhibition (in the low nanomolar range) and selectivity (> 100-fold) can be attained with inhibitors containing only one amide bond. X-ray crystal structures of matrilysin (MMP-7) with two different inhibitors bound confirm that imidazole is an excellent amide bond isostere. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0960-894x(96)00283-1

文献信息

• US6635621B1
  申请人：——

  公开号：US6635621B1

  公开（公告）日：2003-10-21