4-(azidomethyl)-2'-(3-bromophenyl)-2,4'-bioxazole | 1447274-07-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(azidomethyl)-2'-(3-bromophenyl)-2,4'-bioxazole
• CAS: 1447274-07-8
• 化学式: C₁₃H₈BrN₅O₂
• 分子量: 346.143
• InChiKey: ZYQHWBBEZKWPAZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  100.82
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  4-(azidomethyl)-2'-(3-bromophenyl)-2,4'-bioxazole 在 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 1-羟基苯并三唑 、 caesium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 7.08h， 生成 methyl 2'-(3'-(4-((2-(((t-butoxy)carbonyl)amino)-3-methylbutanamido)methyl)-[2,4'-bioxazol]-2'-yl)-[1,1'-biphenyl]-3-yl)-[2,4'-bioxazole]-4-carboxylate
  参考文献：
  名称：

  Macrocyclic biphenyl tetraoxazoles: Synthesis, evaluation as G-quadruplex stabilizers and cytotoxic activity

  摘要：

  A series of macrocyclic biphenyl tetraoxazoles was synthesized. The latter stages of the synthetic approach allowed for the addition of varied N-protected alpha-amino acids, which were subsequently deprotected and condensed to provide the desired macrocycles. Improved yields could be realized in the macrocyclization step of their synthesis relative to other macrocyclic G-quadruplex stabilizers. These 24-membered macrocycles were evaluated for their ability to stabilize G-quadruplex DNA and for their relative cytotoxicity against human tumor cells. These biphenyl tetraoxazoles were not strong ligands for G-quadruplex DNA relative to other macrocyclic polyoxazoles. This reduced stabilizing potential did correlate with their comparatively lower cytotoxic activity as observed in the human tumor cell lines, RPMI 8402 and KB3-1. These studies provide useful insights into the conformational requirements for the development of selective and more potent G-quadruplex ligands. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.033
• 作为产物：
  描述：

  methyl 2-(1-(3-bromobenzamido)-2-((triisopropylsilyl)oxy)ethyl)oxazole-4-carboxylate 在 锂硼氢 、 三氯溴甲烷 、 二乙胺基三氟化硫 、 叠氮磷酸二苯酯 、 氟化氢吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 吡啶 、 乙醇 、 二氯甲烷 为溶剂， 反应 39.0h， 生成 4-(azidomethyl)-2'-(3-bromophenyl)-2,4'-bioxazole
  参考文献：
  名称：

  Macrocyclic biphenyl tetraoxazoles: Synthesis, evaluation as G-quadruplex stabilizers and cytotoxic activity

  摘要：

  A series of macrocyclic biphenyl tetraoxazoles was synthesized. The latter stages of the synthetic approach allowed for the addition of varied N-protected alpha-amino acids, which were subsequently deprotected and condensed to provide the desired macrocycles. Improved yields could be realized in the macrocyclization step of their synthesis relative to other macrocyclic G-quadruplex stabilizers. These 24-membered macrocycles were evaluated for their ability to stabilize G-quadruplex DNA and for their relative cytotoxicity against human tumor cells. These biphenyl tetraoxazoles were not strong ligands for G-quadruplex DNA relative to other macrocyclic polyoxazoles. This reduced stabilizing potential did correlate with their comparatively lower cytotoxic activity as observed in the human tumor cell lines, RPMI 8402 and KB3-1. These studies provide useful insights into the conformational requirements for the development of selective and more potent G-quadruplex ligands. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.05.033