5,11,17,23-tetra(2-(Boc-amino)ethyl)-25,27-bis(4-methyleneoxy-4'-methyl-2,2'-bithiazolyl)-26,28-dihydroxycalix[4]arene | 1187776-13-1

• 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-tetra(2-(Boc-amino)ethyl)-25,27-bis(4-methyleneoxy-4'-methyl-2,2'-bithiazolyl)-26,28-dihydroxycalix[4]arene
• CAS: 1187776-13-1
• 化学式: C₇₂H₈₈N₈O₁₂S₄
• 分子量: 1385.8
• InChiKey: CYEPLCOZVULIHU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.98
• 重原子数：
  96.0
• 可旋转键数：
  20.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  263.8
• 氢给体数：
  6.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetra(2-(Boc-amino)ethyl)-25,27-bis(4-methyleneoxy-4'-methyl-2,2'-bithiazolyl)-26,28-dihydroxycalix[4]arene 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 3.0h， 以93%的产率得到5,11,17,23-tetra-(2-aminoethyl)-25,27-bis(4-methyleneoxy-4'-methyl-2,2'-bithiazolyl)-26,28-dihydroxycalix[4]arene tetra-trifluoroacetate salt
  参考文献：
  名称：

  p-Guanidinoethyl calixarene and parent phenol derivatives exhibiting antibacterial activities. Synthesis and biological evaluation

  摘要：

  The tetra-para-guanidinoethyl-calix[4] arene, its distally-disubstituted ether derivatives involving 2,2'-bithiazolyl-or 2,2'-bipyridyl-methyl groups, as well as the para-guanidinoethylphenol and its analogous derivatives have been synthesized, fully characterized and evaluated as antibacterial agents towards both Gram positive and Gram negative reference bacteria. The simple phenolic species showed lower activity than their calixarene analogues, confirming the hypothesis that a synergistic effect should result from the spatial organization of guanidinium and heterocycles on a macrocyclic scaffold. Introduction of the bithiazole and bipyridine substituents enhanced the activity of simple phenol derivatives, reaching, for the two Staphylococcus aureus strains in particular, the values obtained for their calixarenic parents. MTT viability assays were carried out to determine selectivity indexes. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.06.040
• 作为产物：
  描述：

  5,11,17,23-tetra-(2-(Boc-amino)ethyl)-25,26,27,28-calix[4]arene tetrol 、 4-bromomethyl-4'-methyl-2,2'-bithiazole 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 7.5h， 以69%的产率得到5,11,17,23-tetra(2-(Boc-amino)ethyl)-25,27-bis(4-methyleneoxy-4'-methyl-2,2'-bithiazolyl)-26,28-dihydroxycalix[4]arene
  参考文献：
  名称：

  p-Guanidinoethyl calixarene and parent phenol derivatives exhibiting antibacterial activities. Synthesis and biological evaluation

  摘要：

  The tetra-para-guanidinoethyl-calix[4] arene, its distally-disubstituted ether derivatives involving 2,2'-bithiazolyl-or 2,2'-bipyridyl-methyl groups, as well as the para-guanidinoethylphenol and its analogous derivatives have been synthesized, fully characterized and evaluated as antibacterial agents towards both Gram positive and Gram negative reference bacteria. The simple phenolic species showed lower activity than their calixarene analogues, confirming the hypothesis that a synergistic effect should result from the spatial organization of guanidinium and heterocycles on a macrocyclic scaffold. Introduction of the bithiazole and bipyridine substituents enhanced the activity of simple phenol derivatives, reaching, for the two Staphylococcus aureus strains in particular, the values obtained for their calixarenic parents. MTT viability assays were carried out to determine selectivity indexes. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.06.040