p-nitrophenyl N-<<<6-(N-BOC-amino)hexyl>succinamido>-L-alanyl-L-alanyl-L-prolylmethyl>-N-isopropylcarbamate | 157801-10-0

• 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: p-nitrophenyl N-<<<6-(N-BOC-amino)hexyl>succinamido>-L-alanyl-L-alanyl-L-prolylmethyl>-N-isopropylcarbamate
• 英文别名: (4-nitrophenyl) N-[2-[(2S)-1-[(2S)-2-[[(2S)-2-[[4-[6-[(2-methylpropan-2-yl)oxycarbonylamino]hexylamino]-4-oxobutanoyl]amino]propanoyl]amino]propanoyl]pyrrolidin-2-yl]-2-oxoethyl]-N-propan-2-ylcarbamate
• CAS: 157801-10-0
• 化学式: C₃₇H₅₇N₇O₁₁
• 分子量: 775.9
• InChiKey: ZNZFPRXXVYQMFD-ZEZDXWPOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  55
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  238
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  p-nitrophenyl N-<<<6-(N-BOC-amino)hexyl>succinamido>-L-alanyl-L-alanyl-L-prolylmethyl>-N-isopropylcarbamate 在 盐酸 、 甲酸 作用下， 以 乙酸乙酯 为溶剂， 以81%的产率得到p-nitrophenyl N-<<(6-aminohexyl)succinamido>-L-alanyl-L-alanyl-L-prolylmethyl>-N-isopropylcarbamate hydrochloride
  参考文献：
  名称：

  Synthetic Macromolecular Inhibitors of Human Leukocyte Elastase. 1. Synthesis of Peptidyl Carbamates Bound to Water-Soluble Polymers: Poly-.alpha.,.beta.-[N-(2-hydroxyethyl)-D,L-aspartamide] and Poly-.alpha.-[N5-(2-hydroxyethyl)-L-glutamine]

  摘要：

  The design and synthesis of macromolecular peptidyl carbamate inhibitors of human leukocyte elastase (HLE), based on coupling of a low-molecular-weight peptidyl carbamate, succinylalanylalanylprolylmethyl isopropyl carbamate, with a linear hydrophilic polymer, poly-alpha,beta-[N-(2-hydroxyethyl)-D,L-aspartamide] or poly-alpha-[N-5-(2-hydroxyethyl)-L-glutamine], is described. The covalent linkage between a flexible linear polymer and a peptidyl carbamate inhibitor of HLE did not compromise in vitro inhibitory capacity. The macromolecular peptidyl carbamates reported here represent a novel class of elastase inhibitors with a K-i ranging from 35.5 to 2.0 nM.

  DOI：

  10.1021/jm00038a014
• 作为产物：
  描述：

  N-BOC-1,6-己二胺盐酸盐 在 β-烟酰胺单核苷酸 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 乙腈 为溶剂， 反应 5.75h， 生成 p-nitrophenyl N-<<<6-(N-BOC-amino)hexyl>succinamido>-L-alanyl-L-alanyl-L-prolylmethyl>-N-isopropylcarbamate
  参考文献：
  名称：

  Synthetic Macromolecular Inhibitors of Human Leukocyte Elastase. 1. Synthesis of Peptidyl Carbamates Bound to Water-Soluble Polymers: Poly-.alpha.,.beta.-[N-(2-hydroxyethyl)-D,L-aspartamide] and Poly-.alpha.-[N5-(2-hydroxyethyl)-L-glutamine]

  摘要：

  The design and synthesis of macromolecular peptidyl carbamate inhibitors of human leukocyte elastase (HLE), based on coupling of a low-molecular-weight peptidyl carbamate, succinylalanylalanylprolylmethyl isopropyl carbamate, with a linear hydrophilic polymer, poly-alpha,beta-[N-(2-hydroxyethyl)-D,L-aspartamide] or poly-alpha-[N-5-(2-hydroxyethyl)-L-glutamine], is described. The covalent linkage between a flexible linear polymer and a peptidyl carbamate inhibitor of HLE did not compromise in vitro inhibitory capacity. The macromolecular peptidyl carbamates reported here represent a novel class of elastase inhibitors with a K-i ranging from 35.5 to 2.0 nM.

  DOI：

  10.1021/jm00038a014