5,11,17,23-tetra-(ethoxycarbonylmethyl)-25,26,27,28-tetrahydroxycalix[4]arene | 200879-91-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5,11,17,23-tetra-(ethoxycarbonylmethyl)-25,26,27,28-tetrahydroxycalix[4]arene
• 英文别名: Ethyl 2-[11,17,23-tris(2-ethoxy-2-oxoethyl)-25,26,27,28-tetrahydroxy-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]acetate；ethyl 2-[11,17,23-tris(2-ethoxy-2-oxoethyl)-25,26,27,28-tetrahydroxy-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]acetate
• CAS: 200879-91-0
• 化学式: C₄₄H₄₈O₁₂
• 分子量: 768.858
• InChiKey: HWJYUTRRFQRZBQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  56
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  186
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  6-(bromomethyl)-6'-methyl-2,2'-bipyridine 、 5,11,17,23-tetra-(ethoxycarbonylmethyl)-25,26,27,28-tetrahydroxycalix[4]arene 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 以57%的产率得到Ethyl 2-[11,17,23-tris(2-ethoxy-2-oxoethyl)-26,28-dihydroxy-25,27-bis[[6-(6-methylpyridin-2-yl)pyridin-2-yl]methoxy]-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]acetate
  参考文献：
  名称：

  New water-soluble calix[4]arene-based bipyridyl podands incorporating carboxylate groups

  摘要：

  New calixarene-based bis-bipyridyl podands incorporating two sodium (4-oxo)-butanoate or four sodium carboxymethyl groups at the upper rim were synthesised and fully characterised. The (4-oxo)-butanoate derivative bearing unsubstituted bipyridyl arms was not soluble in water at neutral pH, while its 4,4'-dicarboxylate analogue was perfectly soluble, as were the carboxymethyl derivatives. The association of water solubility to the chelating behaviour of the bipyridyl subunits resulted in the ability to complex the unstable copper(I) cation in water, even in the presence of bovine serum albumin. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.01.088
• 作为产物：
  描述：

  5,11,17,23-tetracyanomethyl-25,26,27,28-tetra(benzyloxy)calix[4]arene 在 硫酸 、 水 、 溶剂黄146 作用下， 反应 9.0h， 生成 5,11,17,23-tetra-(ethoxycarbonylmethyl)-25,26,27,28-tetrahydroxycalix[4]arene
  参考文献：
  名称：

  Upper Rim Substitution of Calixarenes: Carboxylic Acids

  摘要：

  单取代（5a）、双取代（4a 和 4b）以及四取代（1a）对位氰基甲基卡利克斯[4]芳烃和双（氰基甲基）卡利克斯[6]芳烃（6a）经过酸和碱诱导的水解反应，转化为相应的对位羧基甲基卡利克斯[4]芳烃（5b、4c、4d、2a 和 6b），而这些产物又进一步转化为甲酯（5c、4e、4f、2b）和乙酯（5d、4g、2c）。然而，立体障碍化合物 7 和 8 及其对应的单体 10 和 11 中的氰基甲基在严格条件下对此反应表现出惰性，未能发生水解。甲酯 2b 可转化为 1,3-二苄基醚（3b）、1,3-二苄酸酯（3c）、四苄基醚（3a）和四苄酸酯（3d）。

  DOI：

  10.1055/s-1997-1359

文献信息

• 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.
• Upper Rim Substitution of Calixarenes: Carboxylic Acids
  作者：Shiv Kumar Sharma、Suseela Kanamathareddy、C. David Gutsche

  DOI：10.1055/s-1997-1359

  日期：1997.11

  The mono- (5a), bis- (4a and 4b), and tetrakis (1a)-p-cyanomethylcalix[4]arenes as well as the bis(cyanomethyl)calix[6]arene (6a) have been transformed both by acid and base induced hydrolysis to the corresponding p-carboxymethylcalix[4]arenes 5b, 4c, 4d, 2a, and 6b which, in turn, were converted to the methyl (5c, 4e, 4f, 2b) and ethyl (5d, 4g, 2c) esters. The cyanomethyl groups in the sterically hindered compounds 7 and 8 and their corresponding monomers 10 and 11, however, were inert to hydrolysis, even under strenuous conditions. The methyl ester 2b can be converted to the 1,3-dibenzyl ether (3b) and the 1,3-dibenzoate (3c) as well as the tetrabenzyl ether (3a) and tetrabenzoate (3d).

  单取代（5a）、双取代（4a 和 4b）以及四取代（1a）对位氰基甲基卡利克斯[4]芳烃和双（氰基甲基）卡利克斯[6]芳烃（6a）经过酸和碱诱导的水解反应，转化为相应的对位羧基甲基卡利克斯[4]芳烃（5b、4c、4d、2a 和 6b），而这些产物又进一步转化为甲酯（5c、4e、4f、2b）和乙酯（5d、4g、2c）。然而，立体障碍化合物 7 和 8 及其对应的单体 10 和 11 中的氰基甲基在严格条件下对此反应表现出惰性，未能发生水解。甲酯 2b 可转化为 1,3-二苄基醚（3b）、1,3-二苄酸酯（3c）、四苄基醚（3a）和四苄酸酯（3d）。
• New water-soluble calix[4]arene-based bipyridyl podands incorporating carboxylate groups
  作者：Maxime Mourer、Jean-Bernard Regnouf-de-Vains

  DOI：10.1016/j.tetlet.2006.01.088

  日期：2006.3

  New calixarene-based bis-bipyridyl podands incorporating two sodium (4-oxo)-butanoate or four sodium carboxymethyl groups at the upper rim were synthesised and fully characterised. The (4-oxo)-butanoate derivative bearing unsubstituted bipyridyl arms was not soluble in water at neutral pH, while its 4,4'-dicarboxylate analogue was perfectly soluble, as were the carboxymethyl derivatives. The association of water solubility to the chelating behaviour of the bipyridyl subunits resulted in the ability to complex the unstable copper(I) cation in water, even in the presence of bovine serum albumin. (c) 2006 Elsevier Ltd. All rights reserved.