(E)-2-(3-hydroxy-1,4-dioxo-1,4-dihydronaphthalene-2-yl)vinyl acetate | 1091627-08-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (E)-2-(3-hydroxy-1,4-dioxo-1,4-dihydronaphthalene-2-yl)vinyl acetate
• 英文别名: (E)-2-(3-hydroxy-1,4-dioxo-1,4-dihydronaphthalen-2-yl)vinyl acetate
• CAS: 1091627-08-5
• 化学式: C₁₄H₁₀O₅
• 分子量: 258.23
• InChiKey: ZBHPHZASMUPQBM-VOTSOKGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  80.67
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  2-(1-hydroxy-3,4-dioxonaphthalen-2-yl)acetaldehyde 、 乙酸酐 在 吡啶 作用下， 反应 12.0h， 以80%的产率得到(E)-2-(3-hydroxy-1,4-dioxo-1,4-dihydronaphthalene-2-yl)vinyl acetate
  参考文献：
  名称：

  Semisynthesis and antitumoral activity of 2-acetylfuranonaphthoquinone and other naphthoquinone derivatives from lapachol

  摘要：

  Ozonolysis of lapachol (1), resulting in an unusual formation of a potent antitumor agent 2-acetylfuranonaphthoquinone (3) along with the expected aldehyde 6, is described. The reaction of lapachol (1) with CAN in dry acetonitrile leading to biologically active furanonaphthoquinones is also reported. The antitumoral activity of the tested compounds on human DU-145 prostate carcinoma cells was evaluated following XTT assay. The results revealed that 2-(1-methylethenyl)-2,3-dihydronaphtho[2,3-b]furan-4,9-dione (5), beta-lapachone (10) and dehydro-beta-lapachone diacetate (11) showed 100% inhibition at 25 mu g/ml. All the tested samples showed dose-dependent activity. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.09.053

文献信息

• Semisynthesis and antitumoral activity of 2-acetylfuranonaphthoquinone and other naphthoquinone derivatives from lapachol
  作者：Kenneth O. Eyong、Ponminor S. Kumar、Victor Kuete、Gabriel N. Folefoc、Ephriam A. Nkengfack、Sundarababu Baskaran

  DOI：10.1016/j.bmcl.2008.09.053

  日期：2008.10

  Ozonolysis of lapachol (1), resulting in an unusual formation of a potent antitumor agent 2-acetylfuranonaphthoquinone (3) along with the expected aldehyde 6, is described. The reaction of lapachol (1) with CAN in dry acetonitrile leading to biologically active furanonaphthoquinones is also reported. The antitumoral activity of the tested compounds on human DU-145 prostate carcinoma cells was evaluated following XTT assay. The results revealed that 2-(1-methylethenyl)-2,3-dihydronaphtho[2,3-b]furan-4,9-dione (5), beta-lapachone (10) and dehydro-beta-lapachone diacetate (11) showed 100% inhibition at 25 mu g/ml. All the tested samples showed dose-dependent activity. (C) 2008 Elsevier Ltd. All rights reserved.