2-(guanidino)ethyl-4-[4-methyleneoxy-4'-methyl-2,2'-bithiazolyl]-benzene trifluoroacetate salt | 1350179-95-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(guanidino)ethyl-4-[4-methyleneoxy-4'-methyl-2,2'-bithiazolyl]-benzene trifluoroacetate salt
• 英文别名: 2-[2-[4-[[2-(4-Methyl-1,3-thiazol-2-yl)-1,3-thiazol-4-yl]methoxy]phenyl]ethyl]guanidine;2,2,2-trifluoroacetic acid
• CAS: 1350179-95-1
• 化学式: C₂HF₃O₂*C₁₇H₁₉N₅OS₂
• 分子量: 487.527
• InChiKey: FULQGBPHENLFDV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  193
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  [2-((N,N'-di-Boc)-guanidino)ethyl]-4-[4-methyleneoxy-4'-methyl-2,2'-bithiazolyl]-benzene 、 三氟乙酸 以 二氯甲烷 为溶剂， 反应 3.0h， 以98%的产率得到2-(guanidino)ethyl-4-[4-methyleneoxy-4'-methyl-2,2'-bithiazolyl]-benzene 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

文献信息

• p-Guanidinoethyl calixarene and parent phenol derivatives exhibiting antibacterial activities. Synthesis and biological evaluation
  作者：Maxime Mourer、Hugues Massimba Dibama、Stéphane Fontanay、Marion Grare、Raphaël E. Duval、Chantal Finance、Jean-Bernard Regnouf-de-Vains

  DOI：10.1016/j.bmc.2009.06.040

  日期：2009.8

  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.