((S)-1-{(S)-1-[(Dimethyl-phosphinoyl)-hydroxy-methyl]-3-methyl-butylcarbamoyl}-3-methyl-butyl)-carbamic acid benzyl ester | 214001-92-0

• 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: ((S)-1-{(S)-1-[(Dimethyl-phosphinoyl)-hydroxy-methyl]-3-methyl-butylcarbamoyl}-3-methyl-butyl)-carbamic acid benzyl ester
• 英文别名: benzyl N-[(2S)-1-[[(2S)-1-dimethylphosphoryl-1-hydroxy-4-methylpentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate
• CAS: 214001-92-0
• 化学式: C₂₂H₃₇N₂O₅P
• 分子量: 440.52
• InChiKey: QZFISQNQFLQPHB-CHEUHSMRSA-N

物化性质

• 沸点：
  679.201±55.00 °C(Press: 760.00 Torr)(predicted)
• 密度：
  1.115±0.06 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ((S)-1-{(S)-1-[(Dimethyl-phosphinoyl)-hydroxy-methyl]-3-methyl-butylcarbamoyl}-3-methyl-butyl)-carbamic acid benzyl ester 在 戴斯-马丁氧化剂 、 叔丁醇 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以87%的产率得到{(S)-1-[(S)-1-(Dimethyl-phosphinoanecarbonyl)-3-methyl-butylcarbamoyl]-3-methyl-butyl}-carbamic acid benzyl 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：

  2-甲基-2-丙基[(2S)-4-甲基-1-氧代-2-戊烷基]氨基甲酸酯 在 palladium on activated charcoal N-甲基吗啉 、 potassium fluoride 、 氢气 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.5h， 生成 ((S)-1-{(S)-1-[(Dimethyl-phosphinoyl)-hydroxy-methyl]-3-methyl-butylcarbamoyl}-3-methyl-butyl)-carbamic acid benzyl 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