2-hydroxymethyl-5-(2-hydroxynaphthyl)naphtho[2,1-d]oxazole | 1612164-86-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-hydroxymethyl-5-(2-hydroxynaphthyl)naphtho[2,1-d]oxazole
• 英文别名: 1-[2-(Hydroxymethyl)benzo[g][1,3]benzoxazol-5-yl]naphthalen-2-ol
• CAS: 1612164-86-9
• 化学式: C₂₂H₁₅NO₃
• 分子量: 341.366
• InChiKey: HOVKFJJVPZBOIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  66.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-hydroxymethyl-5-(2-hydroxynaphthyl)naphtho[2,1-d]oxazole 、 乙酸酐 反应 2.0h， 以90%的产率得到2-methoxy-carbonylmethyl-5-(2-acetyloxynaphthyl)naphtho[2,1-d]oxazole
  参考文献：
  名称：

  Synthesis, molecular structure, DNA-binding, cytotoxicity, apoptosis and antioxidant activity of compounds containing aryloxazole

  摘要：

  Three novel aryloxazole compounds 1-3 were synthesized and characterized. The crystal structures of compounds 2 and 3 show that N atom locates at β-position and O atom at α-position in naphthalene cycle. The DNA binding constants for compounds 1-3 are 4.44 × 10(3), 5.31 × 10(3) and 2.64 × 10(3) M(-1), respectively. The viscosity measurements indicate that these compounds intercalate between the DNA base pairs. Upon irradiation, compounds 1-3 can effectively cleave pBR322 DNA. The cytotoxicity of the compounds against BEL-7402, A549, MG-63 and SKBR-3 were assayed by MTT method. The apoptosis and cell cycle arrest were investigated towards A549 cells. The antioxidant activities of the compounds against hydroxyl radicals were also explored.

  DOI：

  10.1016/j.ejmech.2014.04.053
• 作为产物：
  描述：

  C.I.酸性橙108 、 2-萘酚 在 copper dichloride 作用下， 以 乙腈 为溶剂， 反应 20.0h， 以40%的产率得到2-hydroxymethyl-5-(2-hydroxynaphthyl)naphtho[2,1-d]oxazole
  参考文献：
  名称：

  Synthesis, molecular structure, DNA-binding, cytotoxicity, apoptosis and antioxidant activity of compounds containing aryloxazole

  摘要：

  Three novel aryloxazole compounds 1-3 were synthesized and characterized. The crystal structures of compounds 2 and 3 show that N atom locates at β-position and O atom at α-position in naphthalene cycle. The DNA binding constants for compounds 1-3 are 4.44 × 10(3), 5.31 × 10(3) and 2.64 × 10(3) M(-1), respectively. The viscosity measurements indicate that these compounds intercalate between the DNA base pairs. Upon irradiation, compounds 1-3 can effectively cleave pBR322 DNA. The cytotoxicity of the compounds against BEL-7402, A549, MG-63 and SKBR-3 were assayed by MTT method. The apoptosis and cell cycle arrest were investigated towards A549 cells. The antioxidant activities of the compounds against hydroxyl radicals were also explored.

  DOI：

  10.1016/j.ejmech.2014.04.053