octaethyl{[25,26,27,28-tetrahydroxypentacyclo[19.3.1.1(3,7).1(9,13).1(15,19)]octacosa-1(25),3(28),4,6,9(27),10,12,15(26),16,18,21,23-dodecaene-5,11,17,23-tetrayl]tetramethanediyl}tetrakis(phosphonate) | 124028-46-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: octaethyl{[25,26,27,28-tetrahydroxypentacyclo[19.3.1.1(3,7).1(9,13).1(15,19)]octacosa-1(25),3(28),4,6,9(27),10,12,15(26),16,18,21,23-dodecaene-5,11,17,23-tetrayl]tetramethanediyl}tetrakis(phosphonate)
• 英文别名: 5,11,17,23-tetra-[(diethylphosphono)methyl]-25,27,26,28-tetrahydroxycalix[4]arene；5,11,17,23-tetrakis[(diethylphosphono)methyl]-25,26,27,28-tetrahydroxycalix[4]arene；5,11,17,23-Tetrakis(diethoxyphosphorylmethyl)pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaene-25,26,27,28-tetrol
• CAS: 124028-46-2
• 化学式: C₄₈H₆₈O₁₆P₄
• 分子量: 1024.95
• InChiKey: VJSPNQSNHMOHEG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  68
• 可旋转键数：
  24
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  223
• 氢给体数：
  4
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  octaethyl{[25,26,27,28-tetrahydroxypentacyclo[19.3.1.1(3,7).1(9,13).1(15,19)]octacosa-1(25),3(28),4,6,9(27),10,12,15(26),16,18,21,23-dodecaene-5,11,17,23-tetrayl]tetramethanediyl}tetrakis(phosphonate) 在 盐酸 作用下， 反应 20.0h， 生成 5,11,17,23-tetrakis(dihydroxyphosphonoyl)methyl-25,26,27,28-tetrahydroxycalix<4>arene
  参考文献：
  名称：

  卡利沙芳烃的氯甲基化和新型水溶性大环宿主的合成

  摘要：

  在室温下，使用氯甲基正辛基醚和 SnCl4 在氯仿中对 calix[4]芳烃 1a 以及 calix[6]芳烃 1b 和 calix[8]芳烃 1c 的甲醚进行氯甲基化，首次以良好的产率进行了。氯甲基化产物 2a-c 已被用作中间体，在卡利沙芳烃上引入膦酸基团，使这些大环具有水溶性，并可能在宿主客体化学中发挥作用。

  DOI：

  10.1016/s0040-4020(01)80077-6
• 作为产物：
  描述：

  杯[4]芳烃 在 溶剂黄146 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.5h， 生成 octaethyl{[25,26,27,28-tetrahydroxypentacyclo[19.3.1.1(3,7).1(9,13).1(15,19)]octacosa-1(25),3(28),4,6,9(27),10,12,15(26),16,18,21,23-dodecaene-5,11,17,23-tetrayl]tetramethanediyl}tetrakis(phosphonate)
  参考文献：
  名称：

  四[{-[（二乙基膦酰基）甲基]}杯[4]芳烃的新型高效合成途径

  摘要：

  四[对-（卤代甲基）]和四[对-（氨基甲基）]杯[4]芳烃衍生物已应用了各种操作条件，以改善5,11,17,23-四[[二乙基膦酰基）的合成甲基] -25,26,27,28-四羟基杯[4]芳烃。选择了两个新的高产合成途径，第一个涉及25,26,27,28-四羟基-5,11,17,23-四[[三甲基氨基）甲基]杯[4]芳烃，四碘化物，DMF和10当量。亚磷酸三乙酯（（EtO）3 P），而另一种是5,11,17,23-四（溴甲基）-25,26,27,28-四羟基杯[4]芳烃，CH 2 Cl 2，并且只有4个当量。（ETO）的2 P.

  DOI：

  10.1002/hlca.201100413

文献信息

• A new water-soluble calix[4]arene podand incorporating p-phosphonate groups and 2,2′-bipyridine units
  作者：Nicolas Psychogios、Jean-Bernard Regnouf-de-Vains

  DOI：10.1016/s0040-4039(02)01843-9

  日期：2002.10

  A new water-soluble calix[4]arene-based bipyridyl podand was prepared by incorporation at the upper rim of four phosphonate groups; the association of its hydrophilic and chelating properties was positively evaluated in the complexation of copper(I) in water.

  通过在四个膦酸酯基团的上边缘结合，制备了一种新的基于水溶性杯[4]芳烃的联吡啶荚果。在水中铜（I）的络合过程中，对其亲水性和螯合性能的关联得到了积极的评估。
• Anti-mycobacterial activities of some cationic and anionic calix[4]arene derivatives
  作者：Maxime Mourer、Hugues Massimba Dibama、Patricia Constant、Mamadou Daffé、Jean-Bernard Regnouf-de-Vains

  DOI：10.1016/j.bmc.2012.01.041

  日期：2012.3

  Various polycharged calix[4]arenes were assayed as anti-mycobacterial agents against Mycobacterium tuberculosis, H37Rv strain. The sulfonate, carboxylate and phosphonate anionic species displayed no activity. Cationic derivatives integrating four aminoethyl groups at the upper rim and two 6,6′-dimethyl-2,2′-bipyridyl- or 4,4′-dimethyl-2,2′-bithiazolyl subunits at the lower rim were also found inactive

  测定了多种带电荷的杯[4]芳烃作为抗结核分枝杆菌H 37 Rv菌株的分枝杆菌药物。磺酸盐，羧酸盐和膦酸盐阴离子物质没有活性。还发现阳离子衍生物在下边缘集成了四个氨基乙基，在下边缘集成了两个6,6'-二甲基-2,2'-联吡啶基-或4,4'-二甲基-2,2'-噻唑基亚基，对结核分枝杆菌，而未取代的和5,5'-二甲基-2,2'-联吡啶-类似物的MIC值分别为3.2和0.8μM。除6,6'-二甲基-2,2'-联吡啶基衍生物外，在上缘引入胍基乙基对未取代的5,5'-二甲基-2,2具有很高的抗分枝杆菌活性。 '-联吡啶基–和4,4'-二甲基-2,2'-联氮唑基类似物，其MIC值分别为0.8、0.8和1.6μM，与目前的市售抗结核药相似。还针对耐异烟肼菌株MYC5165评估了另外五种活性物质，从而产生了令人关注的微摩尔或亚微摩尔MIC和IC 50值，约为50。活性比异烟肼高4–125倍。这些初步结果对于开发新型抗结核病药物具有吸引力。
• Thiacalix[4]arene as molecular platform for design of alkaline phosphatase inhibitors
  作者：A. I. Vovk、L. A. Kononets、V. Yu. Tanchuk、A. B. Drapailo、V. I. Kalchenko、V. P. Kukhar

  DOI：10.1007/s10847-009-9607-9

  日期：2010.4

  Effect of thiacalix[4]arene platform on inhibition of alkaline phosphatase by macrocyclic phosphonate is presented in this article. Using tetrakis(dihydroxyphosphorylmethyl) derivatives we have found that phosphonate inhibitor on thiacalix[4]arene platform has displayed stronger inhibition properties towards alkaline phosphatases from bovine intestine mucosa, shrimp and human placenta than its structural calix[4]arene analogue. For elucidation of the molecular mechanism of the inhibition the tested macrocyclic compounds were docked computationally to the active site of alkaline phosphatase from shrimp. The role of thiacalix[4]arene platform in formation of the enzyme-inhibitor complex is discussed. Thiacalix[4]arene as molecular platform for design of alkaline phosphatase inhibitors

  本文介绍了硫杂六[4]炔平台对大环膦酸盐抑制碱性磷酸酶的影响。通过使用四(二羟基磷酰甲基)衍生物，我们发现硫杂[4]炔平台上的膦酸盐抑制剂对牛肠粘膜、虾和人类胎盘中的碱性磷酸酶的抑制作用要强于其结构上的钙[4]炔类似物。为了阐明抑制作用的分子机制，对测试的大环化合物与虾碱性磷酸酶的活性位点进行了对接计算。讨论了硫杂[4]烯平台在形成酶-抑制剂复合物中的作用。硫杂[4]炔作为设计碱性磷酸酶抑制剂的分子平台
• Synthesis and anti-HIV evaluation of water-soluble calixarene-based bithiazolyl podands
  作者：Maxime Mourer、Nicolas Psychogios、Géraldine Laumond、Anne-Marie Aubertin、Jean-Bernard Regnouf-de-Vains

  DOI：10.1016/j.bmc.2009.11.016

  日期：2010.1

  Nine anionic water-soluble calix[4] arene species, incorporating sulfonate, carboxylate or phosphonate groups, six of them incorporating two 2,2'-bithiazole subunits in alternate position at the lower rim, have been synthesised and evaluated as anti-HIV agents on various HIV strains and cells of the lymphocytic lineage (HIV-1 III B/MT4, HIV-1 LAI/CEM-SS, HIV-1 Bal/PBMC), using AZT as reference compound. A toxicity was detected for a minority of compounds on PBMC whereas for the others no cellular toxicity was measured at concentrations up to 100 mu M. Most of the compounds have an antiviral activity in a 10-50 mu M range, and one of them, sulfonylated, displays its activity, whatever the tropism of the virus, at a micromolar concentration. (C) 2009 Elsevier Ltd. All rights reserved.