methyl-2-[(4-ethynylphenoxy)methyl]benzoxazole-5-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: methyl-2-[(4-ethynylphenoxy)methyl]benzoxazole-5-carboxylate
• 英文别名: Methyl 2-[(4-ethynylphenoxy)methyl]-1,3-benzoxazole-5-carboxylate；methyl 2-[(4-ethynylphenoxy)methyl]-1,3-benzoxazole-5-carboxylate
• 化学式: C₁₈H₁₃NO₄
• 分子量: 307.306
• InChiKey: KTTWKJHIQYONTI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  61.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl-2-[(4-ethynylphenoxy)methyl]benzoxazole-5-carboxylate 、 decaborane 以 甲苯 、 乙腈 为溶剂， 反应 18.0h， 以14%的产率得到methyl 2-[(4-carboranylphenoxy)methyl]benzoxazole-5-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of ortho-carborane containing benzoxazole as an inhibitor of hypoxia inducible factor (HIF)-1 transcriptional activity

  摘要：

  ortho-Carborane and adamantane containing benzoxazoles were synthesized by intramolecular dehydration of the corresponding phenoxyacetanilides. Among the compounds synthesized, ortho-carborane containing benzoxazole 2b which has a carboxylic group on the benzoxazole ring, exhibited significant inhibition of hypoxia-induced HIF-1 transcriptional activity with the IC50 value of 14.4 mu M toward HeLa cell-based reporter gene assay. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.04.007
• 作为产物：
  描述：

  对碘苯氧乙酸 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 四丁基氟化铵 、 1-羟基苯并三唑 、 对甲苯磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三苯基膦 、 N,N-二乙基苯胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 5.5h， 生成 methyl-2-[(4-ethynylphenoxy)methyl]benzoxazole-5-carboxylate
  参考文献：
  名称：

  Synthesis and biological evaluation of ortho-carborane containing benzoxazole as an inhibitor of hypoxia inducible factor (HIF)-1 transcriptional activity

  摘要：

  ortho-Carborane and adamantane containing benzoxazoles were synthesized by intramolecular dehydration of the corresponding phenoxyacetanilides. Among the compounds synthesized, ortho-carborane containing benzoxazole 2b which has a carboxylic group on the benzoxazole ring, exhibited significant inhibition of hypoxia-induced HIF-1 transcriptional activity with the IC50 value of 14.4 mu M toward HeLa cell-based reporter gene assay. (C) 2013 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.jorganchem.2013.04.007

文献信息

• Synthesis and biological evaluation of ortho-carborane containing benzoxazole as an inhibitor of hypoxia inducible factor (HIF)-1 transcriptional activity
  作者：Hiroyuki Nakamura、Yuka Yasui、Hyun Seung Ban

  DOI：10.1016/j.jorganchem.2013.04.007

  日期：2013.12

  ortho-Carborane and adamantane containing benzoxazoles were synthesized by intramolecular dehydration of the corresponding phenoxyacetanilides. Among the compounds synthesized, ortho-carborane containing benzoxazole 2b which has a carboxylic group on the benzoxazole ring, exhibited significant inhibition of hypoxia-induced HIF-1 transcriptional activity with the IC50 value of 14.4 mu M toward HeLa cell-based reporter gene assay. (C) 2013 Elsevier B.V. All rights reserved.