phenyl phosphate tri-n-butylammonium salt | 90290-56-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磷酸及其衍生物
• 英文名称: phenyl phosphate tri-n-butylammonium salt
• 英文别名: phenylphosphate tributylammonium salt；N,N-dibutylbutan-1-amine;phenyl dihydrogen phosphate
• CAS: 90290-56-5
• 化学式: C₆H₇O₄P*C₁₂H₂₇N
• 分子量: 359.446
• InChiKey: BHZBQSNQJNXQBJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.85
• 重原子数：
  24.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  70.0
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  phenyl phosphate tri-n-butylammonium salt 在 N,N'-羰基二(1,2,4-三氮唑) 、 三丁基焦磷酸铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 phenyl triphosphate
  参考文献：
  名称：

  Synthesis of Non-Nucleoside Triphosphate Analogues, a New Type of Substrates for Terminal Deoxynucleotidyl Transferase

  摘要：

  A series of non-nucleoside triphosphate analogues were synthesized. In place of the nucleoside fragment, substituents bearing aromatic groups were introduced; the triphosphate component was replaced at alpha, beta, or gamma -positions by phosphonates. alpha-[2-N-(9-Fluorenylmethoxycarbonyl)aminoethylphosphonyl]-beta,gamma -difluoromethylenediphosphonate (IIc) revealed the best substrate properties toward terminal deoxynucleotidyl transferase.

  DOI：

  10.1080/15257770008045460

文献信息

• Synthesis and evaluation of multisubstrate inhibitors of an oncogene-encoded tyrosine-specific protein kinase. 1
  作者：Carolyn H. Kruse、Kenneth G. Holden、M. Lynn Pritchard、John A. Feild、David J. Rieman、Russell G. Greig、George Poste

  DOI：10.1021/jm00117a015

  日期：1988.9

  The synthesis and testing of potential multisubstrate inhibitors of tyrosine-specific protein kinases are described. One of the substrates, ATP, was mimicked by the known kinase inhibitor 5'-[4-(fluorosulfonyl)benzoyl]adenosine, which was covalently linked via the sulfonyl moiety to tyrosine mimics. The resulting multisubstrate inhibitors were tested for their ability to inhibit the transfer of phosphate

  描述了酪氨酸特异性蛋白激酶潜在的多底物抑制剂的合成和测试。底物之一，ATP，是由已知的激酶抑制剂5'-[4-（氟磺酰基）苯甲酰基]腺苷模拟的，后者通过磺酰基部分与酪氨酸模拟物共价连接。测试了所得的多底物抑制剂通过p60v-abl抑制磷酸从ATP转移到蛋白质受体的能力，p60v-abl是由Abelson鼠白血病病毒（A-MuLV）的转化基因（v-abl）编码的酪氨酸激酶。尽管一系列抑制剂显示出中等强度的活性（IC50值低至19 microM），酪氨酸模拟物的修饰没有产生大的影响，这表明它们不作为多底物抑制剂起作用，而是主要通过所有抑制剂共有的腺苷部分结合。通过发现抑制剂缺乏特异性，在相当的浓度下抑制丝氨酸激酶的发现，加强了这种解释。
• Pyrimidine Ribonucleotides with Enhanced Selectivity as P2Y₆ Receptor Agonists: Novel 4-Alkyloxyimino, (S)-Methanocarba, and 5′-Triphosphate γ-Ester Modifications
  作者：Hiroshi Maruoka、Matthew O. Barrett、Hyojin Ko、Dilip K. Tosh、Artem Melman、Lauren E. Burianek、Ramachandran Balasubramanian、Barkin Berk、Stefano Costanzi、T. Kendall Harden、Kenneth A. Jacobson

  DOI：10.1021/jm100287t

  日期：2010.6.10

  The P2Y(6) receptor is a cytoprotective G-protein-coupled receptor (GPCR) activated by UDP (EC50 = 0.30 mu M). We compared and combined modifications to enhance P2Y(6) receptor agonist selectivity, including ribose ring constraint, 5-iodo and 4-alkyloxyimino modifications, and phosphate modifications such as alpha,beta-methylene and extension of the terminal phosphate group into gamma-esters of UTP analogues. The conformationally constrained (S)-methanocarba-UDP is a full agonist (EC50 = 0.042 mu M). 4-Methoxyimino modification of pyrimidine enhanced P2Y(6), preserved P2Y(2) and P2Y(4), and abolished P2Y(14) receptor potency, in the appropriate nucleotide. N-4-Benzyloxy-CDP (15, MRS2964) and N-4-methoxy-Cp3U Cp3U (12, MRS2957) were potent, selective P2Y(6) receptor agonists (EC50 of 0.026 and 0.012 mu M, respectively). A hydrophobic binding region near the nucleobase was explored with receptor modeling and docking. UTP-gamma-aryl and cycloalkyl phosphoesters displayed only intermediate P2Y(6) receptor potency but had enhanced stability in acid and cell membranes. UTP-glucose was inactive, but its (S)-methanocarba analogue and N-4-methoxycytidine 5'-triphospho-gamma-[1]glucose were active (EC50 of 2.47 and 0.18 mu M, respectively). Thus, the potency, selectivity, and stability of pyrimidine nucleotides as P2Y(6) receptor agonists may be enhanced by modest structural changes.
• KRUSE, CAROLYN H.;HOLDEN, KENNETH G.;OFFEN, PRISCILLA H.;PRITCHARD, M. LY+, J. MED. CHEM., 31,(1988) N 9, C. 1768-1772
  作者：KRUSE, CAROLYN H.、HOLDEN, KENNETH G.、OFFEN, PRISCILLA H.、PRITCHARD, M. LY+

  DOI：——

  日期：——