sodium;(2S)-2-[[[ethoxy(hydroxy)phosphoryl]-(2-hydroxyphenyl)methyl]amino]-3-(1H-indol-3-yl)propanoate | 1363568-25-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: sodium;(2S)-2-[[[ethoxy(hydroxy)phosphoryl]-(2-hydroxyphenyl)methyl]amino]-3-(1H-indol-3-yl)propanoate
• CAS: 1363568-25-5
• 化学式: C₂₀H₂₂N₂O₆P*Na
• 分子量: 440.368
• InChiKey: XOBTZRBDJMITNS-XRZIKPEHSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.95
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  水杨醛 、 亚磷酸二乙酯 、 L-色氨酸 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 以41%的产率得到sodium;(2S)-2-[[[ethoxy(hydroxy)phosphoryl]-(2-hydroxyphenyl)methyl]amino]-3-(1H-indol-3-yl)propanoate
  参考文献：
  名称：

  Exploration of α-aminophosphonate N-derivatives as novel, potent and selective inhibitors of protein tyrosine phosphatases

  摘要：

  Seventeen alpha-aminophosphonates are synthesized. Their compositions and structures are established by EA, UV, FT-IR, H-1 NMR, C-13 NMR, P-31 NMR and ESI-MS. Compounds 1-4 are confirmed by X-ray crystallography. PIP inhibition shows compounds 1-5, 12, 15 are moderate competitive inhibitors with some selectivity. The most potent inhibitor is compound 5 with the lowest IC50 value about 6.64 mu M against PTP1B, about 2-fold and 25-fold stronger than against TCPTP and PTP-MEG2 while it doesn't inhibit SHP-1 and SHP-2. The binding constant of 5 to PTP1B is 2.23 x 10(5) M-1 and binding ratio approximates 1:1. Cell viability and apoptosis assays indicate 5 is cell permeable with lower cytotoxicity. The results indicate alpha-aminophosphonates are possibly developed to effective and selective inhibitors of PTPs. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.038

文献信息

• Exploration of α-aminophosphonate N-derivatives as novel, potent and selective inhibitors of protein tyrosine phosphatases
  作者：Qingming Wang、Miaoli Zhu、Ruiting Zhu、Liping Lu、Caixia Yuan、Shu Xing、Xueqi Fu、Yuhua Mei、Qingwei Hang

  DOI：10.1016/j.ejmech.2012.01.038

  日期：2012.3

  Seventeen alpha-aminophosphonates are synthesized. Their compositions and structures are established by EA, UV, FT-IR, H-1 NMR, C-13 NMR, P-31 NMR and ESI-MS. Compounds 1-4 are confirmed by X-ray crystallography. PIP inhibition shows compounds 1-5, 12, 15 are moderate competitive inhibitors with some selectivity. The most potent inhibitor is compound 5 with the lowest IC50 value about 6.64 mu M against PTP1B, about 2-fold and 25-fold stronger than against TCPTP and PTP-MEG2 while it doesn't inhibit SHP-1 and SHP-2. The binding constant of 5 to PTP1B is 2.23 x 10(5) M-1 and binding ratio approximates 1:1. Cell viability and apoptosis assays indicate 5 is cell permeable with lower cytotoxicity. The results indicate alpha-aminophosphonates are possibly developed to effective and selective inhibitors of PTPs. (C) 2012 Elsevier Masson SAS. All rights reserved.