diethyl ((E,E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraenyl)phosphonate | 150466-36-7

• 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: diethyl ((E,E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraenyl)phosphonate
• 英文别名: (E,E,E)-1-diethylphosphono-4,8,12-trimethyl-1,3,7,11-tridecatetraene；diethyl (E,E,E)-4,8,12-trimethyltrideca-1,3,7,11-tetraenylphosphonate；(1E,3E,7E)-1-diethoxyphosphoryl-4,8,12-trimethyltrideca-1,3,7,11-tetraene
• CAS: 150466-36-7
• 化学式: C₂₀H₃₅O₃P
• 分子量: 354.47
• InChiKey: SEIGPRSGRUEVFL-CABIWMKPSA-N

物化性质

• 沸点：
  452.5±45.0 °C(Predicted)
• 密度：
  0.959±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  24
• 可旋转键数：
  12
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  diethyl ((E,E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraenyl)phosphonate 在 吡啶 、 三正丁胺 、 三甲基溴硅烷 、 N,N-二丁基丁烷-1-胺,磷酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.5h， 生成 triammonium (E,E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraenylpyrophosphonate
  参考文献：
  名称：

  Synthesis of Prenyl Pyrophosphonates as New Potent Phosphoantigens Inducing Selective Activation of Human Vγ9Vδ2 T Lymphocytes

  摘要：

  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.

  DOI：

  10.1021/jm049861z
• 作为产物：
  描述：

  Farnesal 、 亚甲基二磷酸四乙酯 在 sodium hydride 作用下， 以 苯 为溶剂， 反应 2.0h， 以60%的产率得到diethyl ((E,E,E)-4,8,12-trimethyl-1,3,7,11-tridecatetraenyl)phosphonate
  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

• Phosphonates useful as modulators of t $g(g)9$g(d)2 lymphocyte activity
  申请人：Montero Jean-Louis

  公开号：US20060241087A1

  公开（公告）日：2006-10-26

  The invention concerns novel phosphonate derivatives, preparation method, use thereof as ligands modulating T γ9δ2 lymphocyte activity and pharmaceutical compositions comprising them.

  这项发明涉及新型膦酸酯衍生物，其制备方法，以及将其用作调节T γ9δ2淋巴细胞活性的配体和包含它们的药物组合物。
• Phosphonate and bisphosphonate analogues of farnesyl pyrophosphate as potential inhibitors of farnesyl protein transferase
  作者：Sarah A Holstein、Diana M Cermak、David F Wiemer、Kriste Lewis、Raymond J Hohl

  DOI：10.1016/s0968-0896(98)00034-0

  日期：1998.6

  Several phosphonate and bisphosphonate analogues of farnesyl pyrophosphate have been prepared for an examination of their ability to inhibit farnesyl protein transferase (FPTase). A Horner-Wadsworth-Emmons condensation of farnesal or geranial with tetraethyl methylenediphosphonate gave the desired vinyl phosphonates, while alkylation of the dimethyl methylphosphonate anion with a terpenoid bromide

  制备了法呢基焦磷酸的几种膦酸酯和双膦酸酯类似物，以检查其抑制法呢基蛋白转移酶（FPTase）的能力。法呢醛或香叶醛与亚甲基二膦酸四乙酯的霍纳-沃兹沃思-埃蒙斯缩合反应得到所需的乙烯基膦酸酯，而甲基膦酸二甲酯阴离子与萜类溴化物烷基化得到相应的饱和膦酸酯。亚甲基二膦酸四乙酯与法呢基溴的烷基化反应得到预期的双膦酸烷基酯，其通过制备亚硒酸苯基酯，氧化为亚硒酸酯并消除而转化为其α，β-不饱和衍生物。以类似的方式，通过与法呢基溴反应，将膦酰基乙酸三乙酯转化为法呢基焦磷酸酯类似物。制备相应的酸后，测试每种化合物对FPTase的抑制作用，浓度最高可达10 microM。这些化合物对FPTase活性的影响变化很大，范围从抑制到令人惊讶地增强。
• 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
• Phosphonate vs. phosphinate elimination during olefination of aldehydes
  作者：Mahavir Prashad

  DOI：10.1016/0040-4039(93)85013-m

  日期：1993.3

  Olefination of aldehydes with O,O,O-triethyl methylmethylenephosphonophosphinate in the presence of magnesium bromide etherate and triethylamine leads to a selective elimination of the phosphonate group over the phosphinate to yield alkenyl(methyl)phosphinates in a convenient manner.

  在溴化镁醚化物和三乙胺的存在下，用O，O，O-三乙基甲基亚甲基膦膦酸酯进行醛的烯烃化导致膦酸酯基上的膦酸酯基的选择性消除，从而以方便的方式产生链烯基（甲基）次膦酸酯。
• Phosphonates useful as modulators of T-gamma-9-delta-2 activity
  申请人：Montero Jean-Louis

  公开号：US20100204184A1

  公开（公告）日：2010-08-12

  The invention concerns novel phosphonate derivatives, preparation method, use thereof as ligands modulating T γ9δ2 lymphocyte activity and pharmaceutical compositions comprising them.

  这项发明涉及新型膦酸盐衍生物、其制备方法，以及将其用作调节T γ9δ2淋巴细胞活性的配体和包含它们的制药组合物。