[(S)-1-((S)-1-{[Bis-(4-chloro-phenyl)-phosphinoyl]-hydroxy-methyl}-3-methyl-butylcarbamoyl)-3-methyl-butyl]-carbamic acid benzyl ester | 187976-68-7

• 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-{[Bis-(4-chloro-phenyl)-phosphinoyl]-hydroxy-methyl}-3-methyl-butylcarbamoyl)-3-methyl-butyl]-carbamic acid benzyl ester
• 英文别名: benzyl N-[(2S)-1-[[(2S)-1-bis(4-chlorophenyl)phosphoryl-1-hydroxy-4-methylpentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate
• CAS: 187976-68-7
• 化学式: C₃₂H₃₉Cl₂N₂O₅P
• 分子量: 633.552
• InChiKey: QNFKOIQOGRDTET-MYABOAQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  42
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 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-{[Bis-(4-chloro-phenyl)-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 1.0h， 以30%的产率得到((S)-1-{(S)-1-[Bis-(4-chloro-phenyl)-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 N-甲基吗啉 、 potassium fluoride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 17.5h， 生成 [(S)-1-((S)-1-{[Bis-(4-chloro-phenyl)-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