2-[1'-hydroxy-1'-(3'-chlorophenyl)methyl]-1,4-dimethoxynaphthalene | 1430807-13-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[1'-hydroxy-1'-(3'-chlorophenyl)methyl]-1,4-dimethoxynaphthalene
• 英文别名: (3-Chlorophenyl)-(1,4-dimethoxynaphthalen-2-yl)methanol；(3-chlorophenyl)-(1,4-dimethoxynaphthalen-2-yl)methanol
• CAS: 1430807-13-8
• 化学式: C₁₉H₁₇ClO₃
• 分子量: 328.795
• InChiKey: ZJKTWMZELJPOGW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 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-1'-(3'-chlorophenyl)methyl]-1,4-dimethoxynaphthalene 在 ammonium cerium (IV) nitrate 、 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 2.0h， 生成 2-(3'-chlorbenzoyl)-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：

  1,4-二甲氧基萘-2-甲醛 、 (3-chlorophenyl)magnesium bromide 以 四氢呋喃 为溶剂， 反应 17.0h， 以97%的产率得到2-[1'-hydroxy-1'-(3'-chlorophenyl)methyl]-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.