diphenyl 1-amino-2-(4-(N,N'-bis(tert-butyloxycarbonyl)guanidino)phenyl)ethyl-phosphonate | 913239-29-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: diphenyl 1-amino-2-(4-(N,N'-bis(tert-butyloxycarbonyl)guanidino)phenyl)ethyl-phosphonate
• 英文别名: tert-butyl N-[N'-[4-(2-amino-2-diphenoxyphosphorylethyl)phenyl]-N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]carbamate
• CAS: 913239-29-9
• 化学式: C₃₁H₃₉N₄O₇P
• 分子量: 610.647
• InChiKey: OWFUANBSBKBMID-UHFFFAOYSA-N

物化性质

• 密度：
  1.22±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  43
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  151
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  diphenyl 1-amino-2-(4-(N,N'-bis(tert-butyloxycarbonyl)guanidino)phenyl)ethyl-phosphonate 在 PS-carbodiimide 、 1-羟基苯并三唑 作用下， 以 二氯甲烷 为溶剂， 反应 3.17h， 生成 diphenyl 1-[(N-2-thiophenesulfonyl-D-seryl)-L-alanyl]amino-2-(4-guanidinophenyl)ethanephosphonate trifluoroacetate
  参考文献：
  名称：

  Diphenyl Phosphonate Inhibitors for the Urokinase-Type Plasminogen Activator:  Optimization of the P4 Position

  摘要：

  This paper describes the structure-activity relationship in a series of tripeptidyl diphenyl phosphonate irreversible urokinase plasminogen activator (uPA) inhibitors, originally derived from an arginyltripeptide. uPA is considered an interesting target in anticancer drug design. The selectivity of these inhibitors for uPA is enhanced by the optimization of the P4 position. The most interesting compound shows an IC50 of 5 nM, with a selectivity index of more than 3000 toward other Arg/Lys-specific proteases such as tissue-type plasminogen activator, plasmin, factor Xa, and thrombin. A synthetic strategy for the preparation of small libraries of diphenyl phosphonate analogues of capped tripeptides is described. It is shown that uPA is irreversibly inhibited, and interactions with the active site were modeled. Finally, a diparacetamol phosphonate analogue was developed to circumvent the release of cytotoxic phenol.

  DOI：

  10.1021/jm060622g
• 作为产物：
  描述：

  4-氨基苯乙醇 在 palladium on activated charcoal 氢气 、 copper(II) bis(trifluoromethanesulfonate) 、 戴斯-马丁氧化剂 、 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 18.0h，