2-[1'-hydroxy-2'-(4'-chlorophenyl)methyl]-1,4-naphthoquinone | 6626-97-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-[1'-hydroxy-2'-(4'-chlorophenyl)methyl]-1,4-naphthoquinone
• 英文别名: 2-[(4-Chlorophenyl)(hydroxy)methyl]naphthalene-1,4-dione；2-[(4-chlorophenyl)-hydroxymethyl]naphthalene-1,4-dione
• CAS: 6626-97-7
• 化学式: C₁₇H₁₁ClO₃
• 分子量: 298.726
• InChiKey: KADASKCECXRFJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  丙二酸二甲酯 、 2-[1'-hydroxy-2'-(4'-chlorophenyl)methyl]-1,4-naphthoquinone 在 ammonium cerium(IV) nitrate 作用下， 以 甲醇 为溶剂， 以57%的产率得到3-chloro-5,5-dimethoxycarbonyl-5,6,11,12-tetrahydro-6,11,12-trioxo-naphthacene
  参考文献：
  名称：

  2-苄基-1,4-萘醌与β-二羰基化合物之间的氧化自由基反应

  摘要：

  描述了2-苄基-1,4-萘醌与β-二羰基化合物之间的氧化自由基反应。β-二羰基化合物的乙酸锰（III）或硝酸铈（IV）硝酸铵氧化产生的亲电子碳中心自由基经过有效地加成至醌环的C-C双键。该自由基反应提供了合成萘并5，12-二酮的新方法。

  DOI：

  10.1016/s0040-4020(01)00754-2
• 作为产物：
  描述：

  1,4-二甲氧基萘-2-甲醛 在 ammonium cerium (IV) nitrate 作用下， 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 17.0h， 生成 2-[1'-hydroxy-2'-(4'-chlorophenyl)methyl]-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

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.
• Oxidative free radical reactions between 2-benzyl-1,4-naphthoquinones and β-dicarbonyl compounds
  作者：An-I Tsai、Yi-Lung Wu、Che-Ping Chuang

  DOI：10.1016/s0040-4020(01)00754-2

  日期：2001.9

  Oxidative free radical reactions between 2-benzyl-1,4-naphthoquinones and β-dicarbonyl compounds are described. Electrophilic carbon-centered radicals produced by the manganese(III) acetate or cerium(IV) ammonium nitrate oxidation of β-dicarbonyl compounds undergo efficient addition to a C–C double bond of quinone ring. This free radical reaction provides a novel method for the synthesis of naphthacene-5

  描述了2-苄基-1,4-萘醌与β-二羰基化合物之间的氧化自由基反应。β-二羰基化合物的乙酸锰（III）或硝酸铈（IV）硝酸铵氧化产生的亲电子碳中心自由基经过有效地加成至醌环的C-C双键。该自由基反应提供了合成萘并5，12-二酮的新方法。