5,11,17,23-tetra-[2-((N,N'-di-Boc)guanidino)ethyl]-25,26,27,28-calix[4]arene tetrol | 888781-22-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚满类
• 英文名称: 5,11,17,23-tetra-[2-((N,N'-di-Boc)guanidino)ethyl]-25,26,27,28-calix[4]arene tetrol
• CAS: 888781-22-4
• 化学式: C₈₀H₁₁₆N₁₂O₂₀
• 分子量: 1565.87
• InChiKey: UUZRUQKZCXYEDG-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]-25,26,27,28-calix[4]arene tetrol 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 1.0h， 以95%的产率得到para-guanidinoethylcalix[4]arene tetratrifluoroacetate
  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)-25,26,27,28-calix[4]arene tetrol tetra-trifluoroacetate salt 在 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 以65%的产率得到5,11,17,23-tetra-[2-((N,N'-di-Boc)guanidino)ethyl]-25,26,27,28-calix[4]arene tetrol
  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

文献信息

• Functional organisation and gain of activity: The case of the antibacterial tetra-para-guanidinoethyl-calix[4]arene
  作者：Maxime Mourer、Raphaël E. Duval、Chantal Finance、Jean-Bernard Regnouf-de-Vains

  DOI：10.1016/j.bmcl.2006.02.072

  日期：2006.6

  The antibacterial activities of the para-guanidinoethylphenol and of its cyclic tetramer, the tetra-para-guanidinoethylcalix[4]arene, have been evaluated on reference Gram-positive and Gram-negative bacteria. Antibiotic disk diffusion assays completed by micromethod technique were employed to determine if a synergistic effect could be expected from the spatial organisation of the monomer into its cyclic tetrameric analogue. Disk diffusion assays and microdilution experiments revealed better properties for the calixarene species, with a real and important gain of activity with regards to the monomer. (c) 2006 Elsevier Ltd. All rights reserved.