Methyl 4-[4-(4-heptoxyphenyl)phenyl]benzoate | 1228271-69-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Methyl 4-[4-(4-heptoxyphenyl)phenyl]benzoate
• CAS: 1228271-69-9
• 化学式: C₂₇H₃₀O₃
• 分子量: 402.533
• InChiKey: AAPIHEYYTAEPFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 4-[4-(4-heptoxyphenyl)phenyl]benzoate 在 4-二甲氨基吡啶 、 十六烷基三甲基溴化铵 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 potassium hydroxide 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 二氯甲烷 为溶剂， 反应 99.5h， 生成 methyl ((S)-5-((tert-butoxycarbonyl)amino)-2-(4''-(heptyloxy)-[1,1':4',1''-terphenyl]-4-carboxamido)pentanoyl)-L-threonyl-L-prolinate
  参考文献：
  名称：

  Total synthesis and structure–activity relationships of new echinocandin-like antifungal cyclolipohexapeptides

  摘要：

  A series of new echinocandin-like cyclolipohexapeptides were designed and total synthesized via solution phase [3 + 3]-segment coupling strategy with an attempt to improve antifungal activity. The designed compounds showed potent antifungal activities with broad spectrum. In particular, 11 compounds (i.e. 28a-e, 28g, 28i-j, 29a, 29c and 29e) showed better in vitro antifungal activities against Candida albicans or Aspergillus fumigatus than caspofungin. Moreover, the synthesized compounds provided new SAR information for the echinocandins. The findings in this work suggested that the "left" tripeptide segment of cyclolipohexapeptide scaffold might be a hydrophilic structural motif, whereas the "right" lipopeptide segment was preferred as a hydrophobic core. The amino acid component of the cyclolipohexapeptide scaffold could significantly affect the SAR of the side chains. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.054
• 作为产物：
  描述：

  4-羟基-4'-溴联苯 在 正丁基锂 、 palladium diacetate 、 sodium carbonate 、 potassium carbonate 、 三苯基膦 作用下， 以 丙醇 、 甲基叔丁基醚 、 甲苯 、 丁酮 为溶剂， 反应 14.17h， 生成 Methyl 4-[4-(4-heptoxyphenyl)phenyl]benzoate
  参考文献：
  名称：

  Total synthesis and structure–activity relationships of new echinocandin-like antifungal cyclolipohexapeptides

  摘要：

  A series of new echinocandin-like cyclolipohexapeptides were designed and total synthesized via solution phase [3 + 3]-segment coupling strategy with an attempt to improve antifungal activity. The designed compounds showed potent antifungal activities with broad spectrum. In particular, 11 compounds (i.e. 28a-e, 28g, 28i-j, 29a, 29c and 29e) showed better in vitro antifungal activities against Candida albicans or Aspergillus fumigatus than caspofungin. Moreover, the synthesized compounds provided new SAR information for the echinocandins. The findings in this work suggested that the "left" tripeptide segment of cyclolipohexapeptide scaffold might be a hydrophilic structural motif, whereas the "right" lipopeptide segment was preferred as a hydrophobic core. The amino acid component of the cyclolipohexapeptide scaffold could significantly affect the SAR of the side chains. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.01.054

文献信息

• Total synthesis and structure–activity relationships of new echinocandin-like antifungal cyclolipohexapeptides
  作者：Jianzhong Yao、Hongming Liu、Ting Zhou、Hai Chen、Zhenyuan Miao、Chunquan Sheng、Wannian Zhang

  DOI：10.1016/j.ejmech.2012.01.054

  日期：2012.4

  A series of new echinocandin-like cyclolipohexapeptides were designed and total synthesized via solution phase [3 + 3]-segment coupling strategy with an attempt to improve antifungal activity. The designed compounds showed potent antifungal activities with broad spectrum. In particular, 11 compounds (i.e. 28a-e, 28g, 28i-j, 29a, 29c and 29e) showed better in vitro antifungal activities against Candida albicans or Aspergillus fumigatus than caspofungin. Moreover, the synthesized compounds provided new SAR information for the echinocandins. The findings in this work suggested that the "left" tripeptide segment of cyclolipohexapeptide scaffold might be a hydrophilic structural motif, whereas the "right" lipopeptide segment was preferred as a hydrophobic core. The amino acid component of the cyclolipohexapeptide scaffold could significantly affect the SAR of the side chains. (C) 2012 Elsevier Masson SAS. All rights reserved.