5,11,17,23-tetrakis(5-(4-(2-[O-(β-D-galactopyranosyl)-(1->4)-(β-D-glucopyranosyl)thio]ethylcarbamoyl)-1H-1,2,3-triazol-1-yl)pentylcarbamoyl)-25,26,27,28-tetrakis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-calix[4]arene | 1326719-93-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5,11,17,23-tetrakis(5-(4-(2-[O-(β-D-galactopyranosyl)-(1->4)-(β-D-glucopyranosyl)thio]ethylcarbamoyl)-1H-1,2,3-triazol-1-yl)pentylcarbamoyl)-25,26,27,28-tetrakis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-calix[4]arene
• 英文别名: 6-[4-[[3-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]sulfanylpropanoylamino]methyl]triazol-1-yl]-N-[11,17,23-tris[6-[4-[[3-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]sulfanylpropanoylamino]methyl]triazol-1-yl]hexanoylamino]-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: 1326719-93-0
• 化学式: C₁₅₂H₂₃₆N₂₀O₆₄S₄
• 分子量: 3495.91
• InChiKey: MYZMAFISPBUEHN-VXQNXOBRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -14.1
• 重原子数：
  240
• 可旋转键数：
  108
• 环数：
  17.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  1280
• 氢给体数：
  36
• 氢受体数：
  76

反应信息

• 作为产物：
  描述：

  5,11,17,23-tetrakis(5-(4-(2-[O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-1-thio-β-D-glucopyranosyl)thio]ethylcarbamoyl)-1H-1,2,3-triazol-1-yl)pentylcarbamoyl)-25,26,27,28-tetrakis(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)-calix[4]arene 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 5,11,17,23-tetrakis(5-(4-(2-[O-(β-D-galactopyranosyl)-(1->4)-(β-D-glucopyranosyl)thio]ethylcarbamoyl)-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