5,11,17,23-tetra-tert-butyl-25-(3-bromopropyloxy)-27-(3-nalidixoylpropyloxy)-26,28-dihydroxycalix[4]arene | 1352929-05-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 5,11,17,23-tetra-tert-butyl-25-(3-bromopropyloxy)-27-(3-nalidixoylpropyloxy)-26,28-dihydroxycalix[4]arene
• CAS: 1352929-05-5
• 化学式: C₆₂H₇₇BrN₂O₇
• 分子量: 1042.21
• InChiKey: XBJUVVUNLFWHQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.79
• 重原子数：
  72.0
• 可旋转键数：
  11.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  120.11
• 氢给体数：
  2.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  5,11,17,23-tetra-tert-butyl-25-(3-bromopropyloxy)-27-(3-nalidixoylpropyloxy)-26,28-dihydroxycalix[4]arene 、 penicillin V potassium 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以73%的产率得到3-[[5,11,17,23-tetratert-butyl-27-[3-(1-ethyl-7-methyl-4-oxo-1,8-naphthyridine-3-carbonyl)oxypropoxy]-26,28-dihydroxy-25-pentacyclo[19.3.1.13,7.19,13.115,19]octacosa-1(24),3,5,7(28),9,11,13(27),15(26),16,18,21(25),22-dodecaenyl]oxy]propyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-[(2-phenoxyacetyl)amino]-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
  参考文献：
  名称：

  Molecular drug-organiser: Synthesis, characterization and biological evaluation of penicillin V and/or nalidixic acid calixarene-based podands

  摘要：

  Two well-known antibiotic heterocycles, the 'quinolone' nalidixic acid and the beta-lactam penicillin V, active at different levels of the bacterial growth process, have been attached via an ether-ester junction to the p-tert-butylcalix[4] arene lower rim, in alternate position. The resulting hydrophobic molecular drug-organisers were fully characterized, and evaluated over two Gram negative and three Gram positive reference strains, using disk diffusion assays with disks impregnated with solution of title compound in pure DMSO. An interesting activity was observed over Staphylococcus aureus ATCC 25923 with the dissymmetrical podand incorporating one penicillin and one nalidixic ester moieties. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.031
• 作为产物：
  描述：

  5,11,17,23-tetra-tert-butyl-25-(3-bromopropyloxy)-26,27,28-trihydroxycalix[4]arene 、 bromopropyl nalidixate 在 potassium carbonate 作用下， 以 乙腈 为溶剂， 反应 48.5h， 以20%的产率得到5,11,17,23-tetra-tert-butyl-25-(3-bromopropyloxy)-27-(3-nalidixoylpropyloxy)-26,28-dihydroxycalix[4]arene
  参考文献：
  名称：

  Molecular drug-organiser: Synthesis, characterization and biological evaluation of penicillin V and/or nalidixic acid calixarene-based podands

  摘要：

  Two well-known antibiotic heterocycles, the 'quinolone' nalidixic acid and the beta-lactam penicillin V, active at different levels of the bacterial growth process, have been attached via an ether-ester junction to the p-tert-butylcalix[4] arene lower rim, in alternate position. The resulting hydrophobic molecular drug-organisers were fully characterized, and evaluated over two Gram negative and three Gram positive reference strains, using disk diffusion assays with disks impregnated with solution of title compound in pure DMSO. An interesting activity was observed over Staphylococcus aureus ATCC 25923 with the dissymmetrical podand incorporating one penicillin and one nalidixic ester moieties. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.031