[4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-[(S)-2-((S)-3-methyl-1-phenylcarbamoyl-butylcarbamoyl)-4-phenyl-butyl]-phosphinic acid | 223550-60-5

• 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: [4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-[(S)-2-((S)-3-methyl-1-phenylcarbamoyl-butylcarbamoyl)-4-phenyl-butyl]-phosphinic acid
• 英文别名: [(2S)-2-[[(2S)-1-anilino-4-methyl-1-oxopentan-2-yl]carbamoyl]-4-phenylbutyl]-[4-(1,3-dioxoisoindol-2-yl)butyl]phosphinic acid
• CAS: 223550-60-5
• 化学式: C₃₅H₄₂N₃O₆P
• 分子量: 631.709
• InChiKey: NWYFRVGJVQHAJF-JOMNFKBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  45
• 可旋转键数：
  16
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  133
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-[(S)-2-((S)-3-methyl-1-phenylcarbamoyl-butylcarbamoyl)-4-phenyl-butyl]-phosphinic acid 在 重氮甲烷 、 sodium hydroxide 、 肼 作用下， 生成 (4-Amino-butyl)-[(S)-2-((S)-3-methyl-1-phenylcarbamoyl-butylcarbamoyl)-4-phenyl-butyl]-phosphinic acid
  参考文献：
  名称：

  Phosphinic acid inhibitors of matrix metalloproteinases

  摘要：

  The matrix metalloproteinase stromelysin-1 (MMP-3) is inhibited more strongly by peptidyl phosphinic acid 7 than by its corresponding phosphonamidate and phosphonate analogs. Extending a benzyl group at P-1' to a phenylethyl group in 8 further increases the potency (K-i = 1.4 nM). Enhanced potency with an extended substituent into the P-3 region was observed.

  DOI：

  10.1016/0960-894x(96)00023-6
• 作为产物：
  描述：

  在 palladium on activated charcoal N,O-双三甲硅基乙酰胺 、 氢气 、 N,N-二异丙基乙胺 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 [4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-[(S)-2-((S)-3-methyl-1-phenylcarbamoyl-butylcarbamoyl)-4-phenyl-butyl]-phosphinic acid
  参考文献：
  名称：

  Phosphinic acid inhibitors of matrix metalloproteinases

  摘要：

  The matrix metalloproteinase stromelysin-1 (MMP-3) is inhibited more strongly by peptidyl phosphinic acid 7 than by its corresponding phosphonamidate and phosphonate analogs. Extending a benzyl group at P-1' to a phenylethyl group in 8 further increases the potency (K-i = 1.4 nM). Enhanced potency with an extended substituent into the P-3 region was observed.

  DOI：

  10.1016/0960-894x(96)00023-6

文献信息

• Phosphinic acid inhibitors of matrix metalloproteinases
  作者：Charles G. Caldwell、Soumya P. Sahoo、Scott A. Polo、Randall R. Eversole、Thomas J. Lanza、Sander G. Mills、Lisa M. Niedzwiecki、Maria Izquierdo-Martin、Benedict C. Chang、Richard K. Harrison、David W. Kuo、T.-Y. Lin、Ross L. Stein、Philippe L. Durette、William K. Hagmann

  DOI：10.1016/0960-894x(96)00023-6

  日期：1996.2

  The matrix metalloproteinase stromelysin-1 (MMP-3) is inhibited more strongly by peptidyl phosphinic acid 7 than by its corresponding phosphonamidate and phosphonate analogs. Extending a benzyl group at P-1' to a phenylethyl group in 8 further increases the potency (K-i = 1.4 nM). Enhanced potency with an extended substituent into the P-3 region was observed.