5,11,17,23-tetrakis(carboxymethyl)calix[4]arene-25,26,27,28-tetrol | 155562-05-3

• 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-tetrakis(carboxymethyl)calix[4]arene-25,26,27,28-tetrol
• 英文别名: 2-[11,17,23-Tris(carboxymethyl)-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]acetic acid
• CAS: 155562-05-3
• 化学式: C₃₆H₃₂O₁₂
• 分子量: 656.643
• InChiKey: IEOIGIQLKJHJBW-UHFFFAOYSA-N

物化性质

• 沸点：
  931.6±65.0 °C(Predicted)
• 密度：
  1.507±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  48
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  230
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetrakis(carboxymethyl)calix[4]arene-25,26,27,28-tetrol 在 氢氧化钾 、 乙酸酐 、 potassium carbonate 、 sodium iodide 作用下， 以 乙醇 、 水 、 丙酮 为溶剂， 反应 84.0h， 生成 bisanhydride of 5,11,17,23-tetrakis(carboxymethyl)-25,26,27,28-tetrakis(benzyloxy)calix[4]arene
  参考文献：
  名称：

  Synthesis and Reactions of Calix[4]arene Bisanhydrides¹

  摘要：

  The tetrabenzyl ether, tetra-p-bromobenzenesulfonate, and tetra-p-methylbenzenesulfonate of p-carboxymethylcalix[4]arene in the 1,3-alternate conformation have been converted to the corresponding bisanhydrides. Reactions of the bisanhydrides with alcohols or amines afford calix[4]arenes carrying two carboxymethyl and two carboalkoxymethyl or two amidomethyl groups on the upper rim positions. The substitution pattern that is established confers molecular chirality on the calixarenes.

  DOI：

  10.1021/jo9822636
• 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 6.0h， 生成 5,11,17,23-tetrakis(carboxymethyl)calix[4]arene-25,26,27,28-tetrol
  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

• Design and synthesis of new polyphosphorylated upper-rim modified calix[4]arenes as potential and selective chelating agents of uranyl ion
  作者：Evelyne Migianu-Griffoni、Cyrille Mbemba、Ramon Burgada、Delphine Lecerclé、Frédéric Taran、Marc Lecouvey

  DOI：10.1016/j.tet.2008.11.076

  日期：2009.2

  New upper-rim polyphosphorylated calix[4]arenes were designed for decorporation of uranium in case of nuclear contamination. A ligand system containing four preorganized 1-hydroxymethylene-1,1-bisphosphonic acid moieties anchored onto a calix[4]arene platform has been developed. Three calix[4]arene-bisphosphonates were efficiently prepared in multi-step syntheses with a variable carbon chain length

  设计了一种新的上边缘多磷酸化杯[4]芳烃，用于在核污染的情况下使铀脱附。已经开发了一种配体系统，该系统包含锚定在杯[4]芳烃平台上的四个预组织的1-羟基亚甲基-1,1-双膦酸部分。通过多步合成有效地制备了三种杯[4]芳烃-双膦酸酯，双膦酸酯和杯[4]芳烃之间的碳链长度可变。确定了对铀酰离子的亲和常数，并将其与双（HEDP）和三（HEDP）膦酸酯（被称为铀酰的有效配体）的亲和常数进行了比较。
• Calixpenams: synthesis, characterization, and biological evaluation of penicillins V and X clustered by calixarene scaffold
  作者：Fazel NASUHI PUR、Karim AKBARI DILMAGHANI

  DOI：10.3906/kim-1307-32

  日期：——

  Four 6-aminopenicillanic acid moieties were grafted at either rim of calix[4]arene, giving 2 novel generations of penicillin, which were named calixpenam. Antibiotic tests showed that they have amplified activity with respect to the corresponding penams against 3 gram-positive nonpenicillinase-producing strains of Streptococcus.

  在卡利克[4]炔的两端接枝了四个 6-氨基青霉烷酸分子，从而产生了两代新型青霉素，并将其命名为卡利克青霉烷。抗生素测试表明，与相应的青霉烷胺相比，它们对 3 种革兰氏阳性不产青霉素酶链球菌菌株的活性有所提高。
• 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.