2-(1'-hydroxy-3'-phenylpropyl)-1,4-dimethoxynaphthalene | 1430807-04-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1'-hydroxy-3'-phenylpropyl)-1,4-dimethoxynaphthalene
• 英文别名: 1-(1,4-Dimethoxynaphthalen-2-yl)-3-phenylpropan-1-ol；1-(1,4-dimethoxynaphthalen-2-yl)-3-phenylpropan-1-ol
• CAS: 1430807-04-7
• 化学式: C₂₁H₂₂O₃
• 分子量: 322.404
• InChiKey: FYKLUHUBNGQKPO-UHFFFAOYSA-N

物化性质

• 沸点：
  516.2±50.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  24
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(1'-hydroxy-3'-phenylpropyl)-1,4-dimethoxynaphthalene 在 ammonium cerium (IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 以98%的产率得到2-(1'-oxo-3'-phenylpropyl)-1,4-naphthoquinone
  参考文献：
  名称：

  Cytotoxicity of lapachol, β-lapachone and related synthetic 1,4-naphthoquinones against oesophageal cancer cells

  摘要：

  Naphthoquinones have been found to have a wide range of biological activities, including cytotoxicity to cancer cells. The secondary metabolites lapachol, alpha- and beta-lapachone and a series of 25 related synthetic 1,4-naphthoquinones were screened against the oesophageal cancer cell line (WHCO1). Most of the compounds exhibited enhanced cytotoxicity (IC50 1.6-11.7 mu M) compared to the current drug of choice cisplatin (IC50 = 16.5 mu M). This study also established that the two new synthetic halogenated compounds 12a and 16a (IC50 = 3.0 and 7.3 mu M) and the previously reported compound 11a (IC50 = 3.9 mu M), were non-toxic to NIH3T3 normal fibroblast cells. Cell death of oesophageal cancer cells by processes involving PARP cleavage caused by 11a was shown to be associated with elevated c-Jun levels, suggesting a role for this pathway in the mechanism of action of this cohort of naphthoquinone compounds. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.048
• 作为产物：
  描述：

  magnesium,ethylbenzene,bromide 、 1,4-二甲氧基萘-2-甲醛 以 四氢呋喃 为溶剂， 反应 17.0h， 以60%的产率得到2-(1'-hydroxy-3'-phenylpropyl)-1,4-dimethoxynaphthalene
  参考文献：
  名称：

  Cytotoxicity of lapachol, β-lapachone and related synthetic 1,4-naphthoquinones against oesophageal cancer cells

  摘要：

  Naphthoquinones have been found to have a wide range of biological activities, including cytotoxicity to cancer cells. The secondary metabolites lapachol, alpha- and beta-lapachone and a series of 25 related synthetic 1,4-naphthoquinones were screened against the oesophageal cancer cell line (WHCO1). Most of the compounds exhibited enhanced cytotoxicity (IC50 1.6-11.7 mu M) compared to the current drug of choice cisplatin (IC50 = 16.5 mu M). This study also established that the two new synthetic halogenated compounds 12a and 16a (IC50 = 3.0 and 7.3 mu M) and the previously reported compound 11a (IC50 = 3.9 mu M), were non-toxic to NIH3T3 normal fibroblast cells. Cell death of oesophageal cancer cells by processes involving PARP cleavage caused by 11a was shown to be associated with elevated c-Jun levels, suggesting a role for this pathway in the mechanism of action of this cohort of naphthoquinone compounds. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.12.048

文献信息

• Cytotoxicity of lapachol, β-lapachone and related synthetic 1,4-naphthoquinones against oesophageal cancer cells
  作者：Suthananda N. Sunassee、Clinton G.L. Veale、Nelusha Shunmoogam-Gounden、Omalaja Osoniyi、Denver T. Hendricks、Mino R. Caira、Jo-Anne de la Mare、Adrienne L. Edkins、Antônio V. Pinto、Eufrânio N. da Silva Júnior、Michael T. Davies-Coleman

  DOI：10.1016/j.ejmech.2012.12.048

  日期：2013.4

  Naphthoquinones have been found to have a wide range of biological activities, including cytotoxicity to cancer cells. The secondary metabolites lapachol, alpha- and beta-lapachone and a series of 25 related synthetic 1,4-naphthoquinones were screened against the oesophageal cancer cell line (WHCO1). Most of the compounds exhibited enhanced cytotoxicity (IC50 1.6-11.7 mu M) compared to the current drug of choice cisplatin (IC50 = 16.5 mu M). This study also established that the two new synthetic halogenated compounds 12a and 16a (IC50 = 3.0 and 7.3 mu M) and the previously reported compound 11a (IC50 = 3.9 mu M), were non-toxic to NIH3T3 normal fibroblast cells. Cell death of oesophageal cancer cells by processes involving PARP cleavage caused by 11a was shown to be associated with elevated c-Jun levels, suggesting a role for this pathway in the mechanism of action of this cohort of naphthoquinone compounds. (C) 2013 Elsevier Masson SAS. All rights reserved.