diphenoxyphosphoryloxy-[(1E,3E,7E)-4,8,12-trimethyltrideca-1,3,7,11-tetraenyl]phosphinic acid | 757220-89-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: diphenoxyphosphoryloxy-[(1E,3E,7E)-4,8,12-trimethyltrideca-1,3,7,11-tetraenyl]phosphinic acid
• CAS: 757220-89-6
• 化学式: C₂₈H₃₆O₆P₂
• 分子量: 530.538
• InChiKey: VGFAMRCNNIHZID-MEQLIVRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.7
• 重原子数：
  36
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  82.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  diphenoxyphosphoryloxy-[(1E,3E,7E)-4,8,12-trimethyltrideca-1,3,7,11-tetraenyl]phosphinic acid 在 N,N-二丁基丁烷-1-胺,磷酸 作用下， 以 四氢呋喃 、 吡啶 为溶剂， 反应 10.0h， 以286 mg的产率得到(E,E,E)-1-pyrophosphono-4,8,12-trimethyl-1,3,7,11-tridecatetraene
  参考文献：
  名称：

  法呢基焦磷酸的乙烯基焦膦酸酯类似物的合成：法呢基蛋白转移酶的新潜在抑制剂

  摘要：

  描述了焦磷酸法呢酯的新生物等排类似物的合成，其中乙烯基焦磷酸酯取代了焦磷酸酯部分。这些化合物是使用 Horner-Wadsworth-Emmons 程序和改进的迈克尔逊反应制备的。已评估它们对法呢基蛋白转移酶的抑制作用。© 2002 Wiley Periodicals, Inc. 杂原子化学 13:654–661, 2002; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.10081

  DOI：

  10.1002/hc.10081
• 作为产物：
  描述：

  Farnesal 在 吡啶 、 三甲基溴硅烷 、 sodium hydride 作用下， 以 甲醇 、 二氯甲烷 、 苯 为溶剂， 反应 10.5h， 生成 diphenoxyphosphoryloxy-[(1E,3E,7E)-4,8,12-trimethyltrideca-1,3,7,11-tetraenyl]phosphinic acid
  参考文献：
  名称：

  法呢基焦磷酸的乙烯基焦膦酸酯类似物的合成：法呢基蛋白转移酶的新潜在抑制剂

  摘要：

  描述了焦磷酸法呢酯的新生物等排类似物的合成，其中乙烯基焦磷酸酯取代了焦磷酸酯部分。这些化合物是使用 Horner-Wadsworth-Emmons 程序和改进的迈克尔逊反应制备的。已评估它们对法呢基蛋白转移酶的抑制作用。© 2002 Wiley Periodicals, Inc. 杂原子化学 13:654–661, 2002; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.10081

  DOI：

  10.1002/hc.10081

文献信息

• Synthesis of Prenyl Pyrophosphonates as New Potent Phosphoantigens Inducing Selective Activation of Human Vγ9Vδ2 T Lymphocytes
  作者：Ibrahim Zgani、Chantal Menut、Michel Seman、Valerie Gallois、Virginie Laffont、Jeanine Liautard、Jean-Pierre Liautard、Marc Criton、Jean-Louis Montero

  DOI：10.1021/jm049861z

  日期：2004.8.1

  gamma9delta2T cells represent the most abundant population of human blood gammadeltaT lymphocytes. They produce and promote strong cytotoxic activity against many pathogens that are implicated in several human infectious diseases. Their activation requires their exposure to small phosphorus-containing antigens in the family of prenyl pyrophosphates and their related biosynthetic precursors such as isopentenyl pyrophosphate (IPP) and dimethylallyl pyrophosphate (DMAPP), which are naturally occurring metabolites in mycobacteria and several other microbial pathogens. The broad specificity in the recognition of these molecules by the T-lymphocyte population expressing a Vgamma9Vdelta2 cell receptor might facilitate their manipulation by designing small potent synthetic agonist ligands. In this paper, we describe the synthesis and the biological evaluation of new pyrophosphonate compounds as new isosteric analogues of natural prenyl pyrophosphates. Several prenyl and alkenyl pyrophosphonate with different chain lengths and degrees of insaturation (24-28, 48-50, and 64-66) were tested as well as the alkoxymethylpyrophosphonic analogue of IPP (compound 76) as its closest isostere. Several of them appeared to be better activators of Vgamma9Vdelta2 T cell proliferation than IPP. These results open the perspective of a potential use of isoprenoides pyrophosphonates as specific immunoregulatory molecules.
• Synthesis of vinyl pyrophosphonate analogues of farnesyl pyrophosphate: New potential inhibitors of farnesyl protein transferase
  作者：Ibrahim Zgani、Chantal Menut、Jean Louis Montéro

  DOI：10.1002/hc.10081

  日期：——

  The synthesis of new bioisosteric analogues of farnesyl pyrophosphate where a vinyl pyrophosphonate replaced the pyrophosphate moiety is described. These compounds have been prepared using a Horner–Wadsworth–Emmons procedure and a modified Michelson reaction. They have been evaluated for the inhibition of farnesyl protein transferase. © 2002 Wiley Periodicals, Inc. Heteroatom Chem 13:654–661, 2002;

  描述了焦磷酸法呢酯的新生物等排类似物的合成，其中乙烯基焦磷酸酯取代了焦磷酸酯部分。这些化合物是使用 Horner-Wadsworth-Emmons 程序和改进的迈克尔逊反应制备的。已评估它们对法呢基蛋白转移酶的抑制作用。© 2002 Wiley Periodicals, Inc. 杂原子化学 13:654–661, 2002; 在线发表于 Wiley InterScience (www.interscience.wiley.com)。DOI 10.1002/hc.10081