<(diphenoxyphosphinyl)methyl>phosphonic acid | 107701-15-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: <(diphenoxyphosphinyl)methyl>phosphonic acid
• 英文别名: Diphenoxyphosphorylmethylphosphonic acid
• CAS: 107701-15-5
• 化学式: C₁₃H₁₄O₆P₂
• 分子量: 328.198
• InChiKey: BVHMLKMKVRPWJQ-UHFFFAOYSA-N

物化性质

• 沸点：
  519.8±56.0 °C(Predicted)
• 密度：
  1.457±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  <(diphenoxyphosphinyl)methyl>phosphonic acid 、 beta-D-半乳糖五乙酸酯 170.0 ℃ 、6.67 Pa 条件下， 反应 0.08h， 生成 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl 1-<<(diphenoxyphosphinyl)methyl>phosphonate>
  参考文献：
  名称：

  Synthesis of certain nucleoside methylenediphosphonate sugars as potential inhibitors of glycosyltransferases

  摘要：

  The synthesis of alpha-D-glucopyranosyl 1-(methylenediphosphonate) (11), alpha-D-galactopyranosyl 1-(methylenediphosphonate) (14), and alpha-D-mannopyranosyl 1-(methylenediphosphonate) (17) has been accomplished. [(Di-phenoxyphosphinyl)methyl]phosphonic acid (diphenyl-MDP) (5), synthesized by two different procedures, was fused with beta-D-glucopyranose pentaacetate followed by catalytic hydrogenation to give 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl methylenediphosphonate (glucose-MDP) (10). The anomeric configuration of 10 was assigned on the basis of NMR spectral studies. Condensation of 10 with 2',3'-di-O-acetyladenosine was accomplished by using 1-(mesitylene-2-sulfonyl)-3-nitro-1,2,4-triazole (MSNT) as coupling agent, and removal of the blocking groups gave adenosine 5'-[(alpha-D-glucopyranosylhydroxyphosphinyl)methyl]phosphonate (20). Uridine 5'-[(alpha-D-galactopyranosylhydroxyphosphinyl)methyl] phosphonate (23) and guanosine 5'-[(alpha-D-mannopyranosylhydroxyphosphinyl)methyl]phosphonate (26) were similarly prepared. Using a specific glycoprotein galactosyltransferase (EC 2.4.1.38) assay, uridine 5'-[(alpha-D-galactopyranosylhydroxyphosphinyl)methyl]phosphonate (23) demonstrated competitive inhibition with an apparent Ki of 97 microM. The adenosine analogue did not inhibit the enzyme. None of the above compounds show any in vitro antitumor or antiviral activity. Such specific inhibitors of glycosyltransferases may serve as specific probes to study various glycosyltransferases that might be involved in the process of metastasis.

  DOI：

  10.1021/jm00391a021
• 作为产物：
  描述：

  bis(trimethylsilyl) <(diphenoxyphosphinyl)methyl>phosphonate 在 水 、 碳酸氢铵 作用下， 生成 <(diphenoxyphosphinyl)methyl>phosphonic acid
  参考文献：
  名称：

  Synthesis of certain nucleoside methylenediphosphonate sugars as potential inhibitors of glycosyltransferases

  摘要：

  The synthesis of alpha-D-glucopyranosyl 1-(methylenediphosphonate) (11), alpha-D-galactopyranosyl 1-(methylenediphosphonate) (14), and alpha-D-mannopyranosyl 1-(methylenediphosphonate) (17) has been accomplished. [(Di-phenoxyphosphinyl)methyl]phosphonic acid (diphenyl-MDP) (5), synthesized by two different procedures, was fused with beta-D-glucopyranose pentaacetate followed by catalytic hydrogenation to give 2,3,4,6-tetra-O-acetyl-alpha-D-glucopyranosyl methylenediphosphonate (glucose-MDP) (10). The anomeric configuration of 10 was assigned on the basis of NMR spectral studies. Condensation of 10 with 2',3'-di-O-acetyladenosine was accomplished by using 1-(mesitylene-2-sulfonyl)-3-nitro-1,2,4-triazole (MSNT) as coupling agent, and removal of the blocking groups gave adenosine 5'-[(alpha-D-glucopyranosylhydroxyphosphinyl)methyl]phosphonate (20). Uridine 5'-[(alpha-D-galactopyranosylhydroxyphosphinyl)methyl] phosphonate (23) and guanosine 5'-[(alpha-D-mannopyranosylhydroxyphosphinyl)methyl]phosphonate (26) were similarly prepared. Using a specific glycoprotein galactosyltransferase (EC 2.4.1.38) assay, uridine 5'-[(alpha-D-galactopyranosylhydroxyphosphinyl)methyl]phosphonate (23) demonstrated competitive inhibition with an apparent Ki of 97 microM. The adenosine analogue did not inhibit the enzyme. None of the above compounds show any in vitro antitumor or antiviral activity. Such specific inhibitors of glycosyltransferases may serve as specific probes to study various glycosyltransferases that might be involved in the process of metastasis.

  DOI：

  10.1021/jm00391a021

文献信息

• Modulators of 5′-nucleotidase, ecto and the use thereof
  申请人：ARCUS BIOSCIENCES, INC.

  公开号：US10981944B2

  公开（公告）日：2021-04-20

  Compounds that modulate the conversion of AMP to adenosine by 5′-nucleotidase, ecto, and compositions containing the compounds and methods for synthesizing the compounds, are described herein. The use of such compounds and compositions for the treatment and/or prevention of a diverse array of diseases, disorders and conditions, including cancer- and immune-related disorders, that are mediated by 5′-nucleotidase, ecto is also provided.

  本文描述了调节 5′-核苷酸酶将 AMP 转化为腺苷的化合物，以及含有这些化合物的组合物和合成这些化合物的方法。还提供了这些化合物和组合物用于治疗和/或预防由 5′-核苷酸酶外切酶介导的各种疾病、失调和病症，包括癌症和免疫相关失调。
• LANG G.; HERRMANN E., Z. ANORG. UND ALLG. CHEM., 536,(1986) N 5, 187-196
  作者：LANG G.、 HERRMANN E.

  DOI：——

  日期：——
• ——
  作者：LANG G.、 HERRMANN E.、 SCHUBERT I.

  DOI：——

  日期：——
• VAGHEFI, M. M.;BERNACKI, R. J.;HENNEN, W. J.;ROBINS, R. K., J. MED. CHEM., 30,(1987) N 8, 1391-1399
  作者：VAGHEFI, M. M.、BERNACKI, R. J.、HENNEN, W. J.、ROBINS, R. K.

  DOI：——

  日期：——
• MODULATORS OF 5'-NUCLEOTIDASE, ECTO AND THE USE THEREOF
  申请人：Arcus Biosciences, Inc.

  公开号：EP3399984A1

  公开（公告）日：2018-11-14