5,11,17,23-tetrakis(dihydroxyphosphonoyl)methyl-25,26,27,28-tetrahydroxycalix<4>arene | 124006-40-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 5,11,17,23-tetrakis(dihydroxyphosphonoyl)methyl-25,26,27,28-tetrahydroxycalix<4>arene
• 英文别名: p-Methylphosphonatocalix[4]arene；[25,26,27,28-tetrahydroxy-11,17,23-tris(phosphonomethyl)-5-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-dodecaenyl]methylphosphonic acid
• CAS: 124006-40-2
• 化学式: C₃₂H₃₆O₁₆P₄
• 分子量: 800.523
• InChiKey: HXGDFDVLRPRMJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  52
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  311
• 氢给体数：
  12
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetrakis(dihydroxyphosphonoyl)methyl-25,26,27,28-tetrahydroxycalix<4>arene 在 sodium hydroxide 作用下， 以 水 为溶剂， 以87%的产率得到5,11,17,23-tetrakis(hydroxyphosphonoyl)methyl-25,26,27,28-tetrahydroxycalix[4]arene sodium salt
  参考文献：
  名称：

  Synthesis and anti-HIV evaluation of water-soluble calixarene-based bithiazolyl podands

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2009.11.016
• 作为产物：
  描述：

  5,11,17,23-tetra(chloromethyl)-25,26,27,28-tetra-hydroxycalix[4]arene 在 盐酸 作用下， 反应 26.0h， 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

文献信息

• 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
• Improvement of catalytic activity of Candida rugosa lipase in the presence of calix[4]arene bearing iminodicarboxylic/phosphonic acid complexes modified iron oxide nanoparticles
  作者：Elif Ozyilmaz、Mevlut Bayrakci、Mustafa Yilmaz

  DOI：10.1016/j.bioorg.2015.12.001

  日期：2016.4

  In the present study, iron oxide magnetite nanoparticles, prepared through a co-precipitation method, were coated with phosphonic acid or iminodicarboxylic acid derivatives of calix[4]arene to modulate their surfaces with different acidic groups. Candida rugosa lipase was then directly immobilized onto the modified nanoparticles through sol-gel encapsulation. The catalytic activities and enantioselectivities of the two encapsulated lipases in the hydrolysis reaction of (R/S)-naproxen methyl ester and (R/S)-2-phenoxypropionic acid methyl ester were assessed. The results showed that the activity and enantioselectivity of the lipase were improved when the lipase was encapsulated in the presence of calixarene-based additives; the encapsulated lipase with the phosphonic acid derivative of calix[4]arene had an excellent rate of enantioselectivity against the (R/S)-naproxen methyl and (R/S)-2-phenoxypropionic acid methyl esters, with E = 350 and 246, respectively, compared to the free enzyme. The encapsulated lipases (Fe-Calix-N(COOH)) and (Fe-Calix-P) showed good loading ability and little loss of enzyme activity, and the stability of the catalyst was very good; they only lost 6-11% of the enzyme's activity after five batches. (C) 2015 Elsevier Inc. All rights reserved.
• ALMI, MARIO;ARDUINI, ARTURO;CASNATI, ALESSANDRO;POCHINI, ANDREA;UNGARO, R+, TETRAHEDRON., 45,(1989) N, C. 2177-2182
  作者：ALMI, MARIO、ARDUINI, ARTURO、CASNATI, ALESSANDRO、POCHINI, ANDREA、UNGARO, R+

  DOI：——

  日期：——