5,11,17,23-tetra-[2-((N,N'-di-Boc)guanidino)ethyl]-25,27-bis(6-methyleneoxy-6'-methyl-2,2'-bipyridyl)-26,28-dihydroxycalix[4]arene | 1187776-20-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 5,11,17,23-tetra-[2-((N,N'-di-Boc)guanidino)ethyl]-25,27-bis(6-methyleneoxy-6'-methyl-2,2'-bipyridyl)-26,28-dihydroxycalix[4]arene
• CAS: 1187776-20-0
• 化学式: C₁₀₄H₁₃₆N₁₆O₂₀
• 分子量: 1930.32
• InChiKey: QDXDUZJBOSIOHM-UHFFFAOYSA-N

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetra-[2-((N,N'-di-Boc)guanidino)ethyl]-25,27-bis(6-methyleneoxy-6'-methyl-2,2'-bipyridyl)-26,28-dihydroxycalix[4]arene 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 3.0h， 以74%的产率得到5,11,17,23-tetra-(2-guanidinoethyl)-25,27-bis(6-methyleneoxy-6'-methyl-2,2'-bipyridyl)-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：

  1,3-二-BOC-2-(三氟甲基磺酰)胍 、 5,11,17,23-tetra-(2-aminoethyl)-25,27-bis(6-methyleneoxy-6'-methyl-2,2'-bipyridyl)-26,28-dihydroxycalix[4]arene hexa-trifluoroacetate salt 在 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 以76%的产率得到5,11,17,23-tetra-[2-((N,N'-di-Boc)guanidino)ethyl]-25,27-bis(6-methyleneoxy-6'-methyl-2,2'-bipyridyl)-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