[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-1-hydroxy-4-methyl-pentyl]-phosphonic acid monomethyl ester | 214001-93-1

• 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)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-1-hydroxy-4-methyl-pentyl]-phosphonic acid monomethyl ester
• 英文别名: [(2S)-1-hydroxy-4-methyl-2-[[(2S)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]pentyl]-methoxyphosphinic acid
• CAS: 214001-93-1
• 化学式: C₂₁H₃₅N₂O₇P
• 分子量: 458.492
• InChiKey: HVGYKJNCTYFNSE-IJXZTRCJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  [(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-1-hydroxy-4-methyl-pentyl]-phosphonic acid monomethyl ester 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 [(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-4-methyl-pentanoyl]-phosphonic acid monomethyl ester
  参考文献：
  名称：

  Novel Peptidyl Phosphorus Derivatives as Inhibitors of Human Calpain I

  摘要：

  Dipeptidyl phosphorus compounds were synthesized as potential bioisosteric mimics of peptide alpha-ketoesters and alpha-ketoacids. alpha-Ketophosphonate Cbz-Leu-Leu-P(O)(OCH3)(2) (1b), containing an alpha-ketoester bioisostere, inhibits human calpain I with an IC50 = 0.43 mu M. The potency of 1b compares very favorably with that of alpha-ketoester Cbz-Leu-Leu-CO2Et (IC50 = 0.60 mu M). Monomethyl ketophosphonate Cbz-Leu-Leu-P(O)(OH)(OCH3) (1a, IC50 = 5.2 mu M), an cl-ketoacid mimic, is less potent. Dibutyl and dibenzyl alpha-ketophosphonates 1c,e,f are much less potent calpain inhibitors than dimethyl alpha-ketophosphonate 1b. alpha-Ketophosphinate 1g (IC50 = 0.37 mu M) and alpha-ketophosphine oxide 1h (IC50 = 0.35 mu M) are also potent calpain inhibitors.

  DOI：

  10.1021/jm980325e
• 作为产物：
  描述：

  N-苄氧羰基-L-亮氨酸 在 N-甲基吗啉 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 生成 [(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-1-hydroxy-4-methyl-pentyl]-phosphonic acid monomethyl ester
  参考文献：
  名称：

  Novel Peptidyl Phosphorus Derivatives as Inhibitors of Human Calpain I

  摘要：

  Dipeptidyl phosphorus compounds were synthesized as potential bioisosteric mimics of peptide alpha-ketoesters and alpha-ketoacids. alpha-Ketophosphonate Cbz-Leu-Leu-P(O)(OCH3)(2) (1b), containing an alpha-ketoester bioisostere, inhibits human calpain I with an IC50 = 0.43 mu M. The potency of 1b compares very favorably with that of alpha-ketoester Cbz-Leu-Leu-CO2Et (IC50 = 0.60 mu M). Monomethyl ketophosphonate Cbz-Leu-Leu-P(O)(OH)(OCH3) (1a, IC50 = 5.2 mu M), an cl-ketoacid mimic, is less potent. Dibutyl and dibenzyl alpha-ketophosphonates 1c,e,f are much less potent calpain inhibitors than dimethyl alpha-ketophosphonate 1b. alpha-Ketophosphinate 1g (IC50 = 0.37 mu M) and alpha-ketophosphine oxide 1h (IC50 = 0.35 mu M) are also potent calpain inhibitors.

  DOI：

  10.1021/jm980325e