diethyl 2-naphthyloxymethylphosphonate | 157768-47-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: diethyl 2-naphthyloxymethylphosphonate
• 英文别名: 2-(Diethoxyphosphorylmethoxy)naphthalene
• CAS: 157768-47-3
• 化学式: C₁₅H₁₉O₄P
• 分子量: 294.287
• InChiKey: QTSIJZGZEZQAOM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  diethyl 2-naphthyloxymethylphosphonate 在 盐酸 作用下， 生成 (Naphthalen-2-yloxymethyl)-phosphonic acid
  参考文献：
  名称：

  A nonhydrolyzable analogue of phosphotyrosine, and related aryloxymethano- and aryloxyethano-phosphonic acids as motifs for inhibition of phosphatases

  摘要：

  Nonhydrolyzable analogues of both stereoisomers of phosphotyrosine, and a series of related aryloxy (or thio) methyl and aryloxy (or thio) ethyl phosphonic acids of the general formula RX-(CH2) -PO3H2 (where X = O or S and n = 1 or 2), have been tested as nonhydrolyzable mimetics of phosphatase substrates. These compounds were tested against a panel of phosphatases (two alkaline phosphatases, a protein-tyrosine phosphatase, and two serine/threonine phosphatases) with different active site motifs. The compounds exhibit competitive inhibition toward all enzymes tested, with the best inhibition expressed toward the Ser/Thr phosphatases. The stereoisomers of the phosphotyrosine analogues exhibited an unexpected difference in their inhibitory properties toward the protein-tyrosine phosphatase from Yersinia. The K-i for the D isomer is 33-fold lower than that of the (L) isomer, and is more than an order of magnitude lower than the reported K, of the substrate L-phosphotyrosine. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.008
• 作为产物：
  描述：

  羟甲基膦酸二乙酯 在 potassium tert-butylate 、 三乙胺 作用下， 以 乙醚 、 二甲基亚砜 为溶剂， 生成 diethyl 2-naphthyloxymethylphosphonate
  参考文献：
  名称：

  A nonhydrolyzable analogue of phosphotyrosine, and related aryloxymethano- and aryloxyethano-phosphonic acids as motifs for inhibition of phosphatases

  摘要：

  Nonhydrolyzable analogues of both stereoisomers of phosphotyrosine, and a series of related aryloxy (or thio) methyl and aryloxy (or thio) ethyl phosphonic acids of the general formula RX-(CH2) -PO3H2 (where X = O or S and n = 1 or 2), have been tested as nonhydrolyzable mimetics of phosphatase substrates. These compounds were tested against a panel of phosphatases (two alkaline phosphatases, a protein-tyrosine phosphatase, and two serine/threonine phosphatases) with different active site motifs. The compounds exhibit competitive inhibition toward all enzymes tested, with the best inhibition expressed toward the Ser/Thr phosphatases. The stereoisomers of the phosphotyrosine analogues exhibited an unexpected difference in their inhibitory properties toward the protein-tyrosine phosphatase from Yersinia. The K-i for the D isomer is 33-fold lower than that of the (L) isomer, and is more than an order of magnitude lower than the reported K, of the substrate L-phosphotyrosine. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.008

文献信息

• Cornforth, John; Wilson, John R. H., Journal of the Chemical Society. Perkin transactions I, 1994, # 14, p. 1897 - 1900
  作者：Cornforth, John、Wilson, John R. H.

  DOI：——

  日期：——
• Synthesis and characterization of a novel class of protein tyrosine phosphatase inhibitors
  作者：Omar A. Ibrahimi、Li Wu、Kang Zhao*、Zhong-Yin Zhang

  DOI：10.1016/s0960-894x(00)00019-6

  日期：2000.3

  Nonpeptidyl aryloxymethylphosphonates were prepared and evaluated as protein tyrosine phosphatase inhibitors. The results suggest that aryloxymethylphosphonates are effective nonhydrolyzable phosphotyrosine surrogates and provide further insight into the molecular mechanisms by which phosphate mimics inhibit phosphatase function. (C) 2000 Elsevier Science Ltd. All rights resereved.
• A nonhydrolyzable analogue of phosphotyrosine, and related aryloxymethano- and aryloxyethano-phosphonic acids as motifs for inhibition of phosphatases
  作者：Subashree Iyer、Jarod M. Younker、Przemyslaw G. Czyryca、Alvan C. Hengge

  DOI：10.1016/j.bmcl.2004.09.008

  日期：2004.12

  Nonhydrolyzable analogues of both stereoisomers of phosphotyrosine, and a series of related aryloxy (or thio) methyl and aryloxy (or thio) ethyl phosphonic acids of the general formula RX-(CH2) -PO3H2 (where X = O or S and n = 1 or 2), have been tested as nonhydrolyzable mimetics of phosphatase substrates. These compounds were tested against a panel of phosphatases (two alkaline phosphatases, a protein-tyrosine phosphatase, and two serine/threonine phosphatases) with different active site motifs. The compounds exhibit competitive inhibition toward all enzymes tested, with the best inhibition expressed toward the Ser/Thr phosphatases. The stereoisomers of the phosphotyrosine analogues exhibited an unexpected difference in their inhibitory properties toward the protein-tyrosine phosphatase from Yersinia. The K-i for the D isomer is 33-fold lower than that of the (L) isomer, and is more than an order of magnitude lower than the reported K, of the substrate L-phosphotyrosine. (C) 2004 Elsevier Ltd. All rights reserved.