2-(1-hydroxy-1-phenylmethyl)-1,4-dimethoxynaphthalene | 1098224-86-2

• 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-phenylmethyl)-1,4-dimethoxynaphthalene
• 英文别名: 2-(1-hydroxybenzyl)-1,4-dimethoxynaphthalene；(1,4-Dimethoxynaphthalen-2-yl)-phenylmethanol
• CAS: 1098224-86-2
• 化学式: C₁₉H₁₈O₃
• 分子量: 294.35
• InChiKey: KWVOGZKDFFNHRM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  22
• 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-phenylmethyl)-1,4-dimethoxynaphthalene 在 三乙基硅烷 、 四丙基高钌酸铵 、 三氟化硼乙醚 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 2-苄基-1,4-二甲氧基萘
  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-基)-苯基甲酮 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 3.0h， 以99%的产率得到2-(1-hydroxy-1-phenylmethyl)-1,4-dimethoxynaphthalene
  参考文献：
  名称：

  金属盐介导的 2-取代-1,4-萘醌的自由基反应

  摘要：

  描述了银 (II) 和锰 (III) 介导的 2-取代-1,4-萘醌自由基反应。α-酮酸与硝酸银 (I) 和过硫酸盐的氧化脱羧产生的酰基自由基在 2-(1-羟烷基)-1,4-萘醌和 2-(1-氨基烷基)-1,4-萘醌。该反应为合成萘并[2,3-c]呋喃-4,9-二酮和苯并[f]异吲哚-4,9-二酮提供了一种有效的方法。在O 2 存在下，β-酮酯的乙酸锰(III)氧化也产生酰基自由基，然后自由基加成为2-(1-酰胺基-烷基)-1,4-萘醌，随后苯并[ f]iso-indole-4,9-diones 产生。

  DOI：

  10.1002/ejoc.201000272

文献信息

• Synthesis and Cytotoxicity of Analogues of the Marine Secondary Metabolite, 2-Deoxylapachol
  作者：Suthananda N. Sunassee、Albert W.W. van Wyk、Omolaja Osoniyi、Denver T. Hendricks、Michael T. Davies-Coleman

  DOI：10.3184/030823407x270437

  日期：2007.12

  The syntheses of four 2-substituted 1,4 naphthoquinones, related to the marine natural product 2-deoxylapachol, are reported. All four synthetic compounds were cytotoxic to WHCO1 oesophageal cancer cells.

  四个 2-取代 1,4 萘醌的合成，与海洋天然产物 2-deoxylapachol 相关。所有四种合成化合物对 WHCO1 食管癌细胞都有细胞毒性。
• 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.
• Metal Salt Mediated Radical Reactions of 2-Substituted-1,4-Naphthoquinones
  作者：Zhen-Yu Lin、Yu-Ling Chen、Chih-Shone Lee、Che-Ping Chuang

  DOI：10.1002/ejoc.201000272

  日期：——

  bond of 2-(1-hydroxyalkyl)-1,4-naphthoquinones and 2-(1-amidoalkyl)-1,4-naphthoquinones. This reaction provides an effective method for the synthesis of naphtho[2,3-c]furan-4,9-diones and benzo[f]isoindole-4,9-diones. In the presence of O 2 , manganese(III) acetate oxidation of β-keto esters also generates acyl radicals, which then undergo radical addition to 2-(1-amido-alkyl)-1,4-naphthoquinones, and

  描述了银 (II) 和锰 (III) 介导的 2-取代-1,4-萘醌自由基反应。α-酮酸与硝酸银 (I) 和过硫酸盐的氧化脱羧产生的酰基自由基在 2-(1-羟烷基)-1,4-萘醌和 2-(1-氨基烷基)-1,4-萘醌。该反应为合成萘并[2,3-c]呋喃-4,9-二酮和苯并[f]异吲哚-4,9-二酮提供了一种有效的方法。在O 2 存在下，β-酮酯的乙酸锰(III)氧化也产生酰基自由基，然后自由基加成为2-(1-酰胺基-烷基)-1,4-萘醌，随后苯并[ f]iso-indole-4,9-diones 产生。