1-[(benzyloxy)carbonyl]prolyl-N1-({[(1,1'-biphenyl-4-yl)methyl](methoxy)phosphoryl}methyl)leucinamide | 860292-56-4

• 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: 1-[(benzyloxy)carbonyl]prolyl-N1-({[(1,1'-biphenyl-4-yl)methyl](methoxy)phosphoryl}methyl)leucinamide
• 英文别名: 1-[(benzyloxy)carbonyl]prolyl-N¹-({[(1,1'-biphenyl-4-yl)methyl](methoxy)phosphoryl}methyl)leucinamide
• CAS: 860292-56-4
• 化学式: C₃₄H₄₂N₃O₆P
• 分子量: 619.698
• InChiKey: IANZWBXAYADPMC-GREBWDRTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.18
• 重原子数：
  44.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  114.04
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  1-[(benzyloxy)carbonyl]prolyl-N1-({[(1,1'-biphenyl-4-yl)methyl](methoxy)phosphoryl}methyl)leucinamide 在 N,N-二(三甲基硅基)乙酰胺 、 碘代三甲硅烷 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以75%的产率得到[[(2S)-4-methyl-2-[[(2S)-pyrrolidine-2-carbonyl]amino]pentanoyl]amino]methyl-[(4-phenylphenyl)methyl]phosphinic acid
  参考文献：
  名称：

  Design, modelling, synthesis and biological evaluation of peptidomimetic phosphinates as inhibitors of matrix metalloproteinases MMP-2 and MMP-8

  摘要：

  Three novel peptidomimetic phosphinate inhibitors have been synthesized and evaluated as inhibitors of matrix metalloprotemases MMP-2 and MMP-8. Their IC50 values are in the micromolar range, and one of them showed to be the most effective inhibitor of MMP-2. The differences in binding affinities for MMP-2 and MMP-8 of the three phosphinates have been rationalized by means of modelling studies and molecular dynamics simulations. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.079
• 作为产物：
  描述：

  (1,1'-biphenyl-4-yl)methylphosphinic acid 在 1-羟基苯并三唑 、 一水合肼 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 21.0h， 生成 1-[(benzyloxy)carbonyl]prolyl-N1-({[(1,1'-biphenyl-4-yl)methyl](methoxy)phosphoryl}methyl)leucinamide
  参考文献：
  名称：

  Design, modelling, synthesis and biological evaluation of peptidomimetic phosphinates as inhibitors of matrix metalloproteinases MMP-2 and MMP-8

  摘要：

  Three novel peptidomimetic phosphinate inhibitors have been synthesized and evaluated as inhibitors of matrix metalloprotemases MMP-2 and MMP-8. Their IC50 values are in the micromolar range, and one of them showed to be the most effective inhibitor of MMP-2. The differences in binding affinities for MMP-2 and MMP-8 of the three phosphinates have been rationalized by means of modelling studies and molecular dynamics simulations. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.04.079