5,11,17,23-tetrakis-(6-azidohexanamido)-25,26,27,28-tetrakis-[2-(2-(2-methoxyethoxy)ethoxy)ethoxy]-calix[4]arene | 1326719-90-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5,11,17,23-tetrakis-(6-azidohexanamido)-25,26,27,28-tetrakis-[2-(2-(2-methoxyethoxy)ethoxy)ethoxy]-calix[4]arene
• 英文别名: 6-azido-N-[11,17,23-tris(6-azidohexanoylamino)-25,26,27,28-tetrakis[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]-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]hexanamide
• CAS: 1326719-90-7
• 化学式: C₈₀H₁₂₀N₁₆O₂₀
• 分子量: 1625.93
• InChiKey: YYKDRFZCHNAOMP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.1
• 重原子数：
  116
• 可旋转键数：
  68
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  322
• 氢给体数：
  4
• 氢受体数：
  28

反应信息

• 作为反应物：
  描述：

  2-[2-(2-propargyloxyethoxy)ethoxy]ethanol-2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-Dgalactopyranosyl)-β-D-glucopyranoside 、 5,11,17,23-tetrakis-(6-azidohexanamido)-25,26,27,28-tetrakis-[2-(2-(2-methoxyethoxy)ethoxy)ethoxy]-calix[4]arene 在 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以80%的产率得到5,11,17,23-tetrakis[5-(4-(2-(2-(2-[(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyloxy)]ethoxy)ethoxy)ethoxymethyl)1H-1,2,3-triazol-1-yl)pentylcarbamoyl]-25,26,27,28-tetrakis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-calix[4]arene
  参考文献：
  名称：

  Glycoclusters presenting lactose on calix[4]arene cores display trypanocidal activity

  摘要：

  A new series of water-soluble tetravalent glycoclusters incorporating beta-lactosyl residues attached to a central calix[4]arene core was synthesised using azide-alkyne Cu(I)-catalysed cycloaddition ('click chemistry'). Carbohydrate moieties were attached either to the upper or lower rim of rigid cone-shaped or partial cone macrocycles via 14-21 atom spacer arms. The glycoclusters with a C(4)-symmetrical arrangement of beta-lactosyl residues showed trypanocidal activity, with one of them showing comparable activity to established anti-trypanosomal drug benznidazole in in vitro anti-parasite assays. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.065
• 作为产物：
  描述：

  叠氮-C5-琥珀酰亚胺酯 、 5,11,17,23-tetraamino-25,26,27,28-tetrakis[2-(2-(2-methoxyethoxy)ethoxy)ethoxy]-calix[4]arene 以 二氯甲烷 为溶剂， 反应 17.0h， 以85%的产率得到5,11,17,23-tetrakis-(6-azidohexanamido)-25,26,27,28-tetrakis-[2-(2-(2-methoxyethoxy)ethoxy)ethoxy]-calix[4]arene
  参考文献：
  名称：

  Glycoclusters presenting lactose on calix[4]arene cores display trypanocidal activity

  摘要：

  A new series of water-soluble tetravalent glycoclusters incorporating beta-lactosyl residues attached to a central calix[4]arene core was synthesised using azide-alkyne Cu(I)-catalysed cycloaddition ('click chemistry'). Carbohydrate moieties were attached either to the upper or lower rim of rigid cone-shaped or partial cone macrocycles via 14-21 atom spacer arms. The glycoclusters with a C(4)-symmetrical arrangement of beta-lactosyl residues showed trypanocidal activity, with one of them showing comparable activity to established anti-trypanosomal drug benznidazole in in vitro anti-parasite assays. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.06.065

文献信息

• Glycoclusters presenting lactose on calix[4]arene cores display trypanocidal activity
  作者：Eva Galante、Corrada Geraci、Sebastiano Sciuto、Vanessa L. Campo、Ivone Carvalho、Renata Sesti-Costa、Paulo M.M. Guedes、João S. Silva、Lionel Hill、Sergey A. Nepogodiev、Robert A. Field

  DOI：10.1016/j.tet.2011.06.065

  日期：2011.8

  A new series of water-soluble tetravalent glycoclusters incorporating beta-lactosyl residues attached to a central calix[4]arene core was synthesised using azide-alkyne Cu(I)-catalysed cycloaddition ('click chemistry'). Carbohydrate moieties were attached either to the upper or lower rim of rigid cone-shaped or partial cone macrocycles via 14-21 atom spacer arms. The glycoclusters with a C(4)-symmetrical arrangement of beta-lactosyl residues showed trypanocidal activity, with one of them showing comparable activity to established anti-trypanosomal drug benznidazole in in vitro anti-parasite assays. (C) 2011 Elsevier Ltd. All rights reserved.