3-[[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy]-2,2-dimethyl-3H-benzo[g][1]benzofuran-4,5-dione | 1439359-40-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: 3-[[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy]-2,2-dimethyl-3H-benzo[g][1]benzofuran-4,5-dione
• CAS: 1439359-40-6
• 化学式: C₂₃H₂₆O₈
• 分子量: 430.455
• InChiKey: AMDWNEOUUQNSLQ-HDWZVLIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-hydroxy-3-(2-methylprop-1-enyl)naphthalene-1,2-dione 在 甲烷磺酸 、 溴 作用下， 以 氯仿 为溶剂， 生成 3-[[(3aR,4R,6R,6aR)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-6-yl]methoxy]-2,2-dimethyl-3H-benzo[g][1]benzofuran-4,5-dione
  参考文献：
  名称：

  A new approach for the synthesis of 3-substituted cytotoxic nor-β-lapachones

  摘要：

  Several studies have demonstrated the cytotoxic potential of nor-beta-lapachone derivative against cancer cells. Considering nor-beta-lapachone as an important prototype, a set of new 3-substituted nor-beta-lapachones was synthesized by a new synthetic route that involves the use of synthetic intermediate generated for coupling with several nucleophiles containing the carbohydrate and 2H-pyrazole substituent moieties. All the compounds were screened against four tumor cell lines. Two of the compounds showed moderate cytotoxicity, while the other compounds strongly inhibit all tested cancer cell lines.

  DOI：

  10.1590/s0103-50532013000100003

文献信息

• A new approach for the synthesis of 3-substituted cytotoxic nor-β-lapachones
  作者：Mariana F. C. Cardoso、Illana M. C. B. da Silva、Helvécio M. dos Santos Júnior、David R. Rocha、Ana Jérsia Araújo、Claudia Pessoa、Manoel O. de Moraes、Letícia V. C. Lotufo、Fernando de C. da Silva、Wilson C. Santos、Vitor F. Ferreira

  DOI：10.1590/s0103-50532013000100003

  日期：——

  Several studies have demonstrated the cytotoxic potential of nor-beta-lapachone derivative against cancer cells. Considering nor-beta-lapachone as an important prototype, a set of new 3-substituted nor-beta-lapachones was synthesized by a new synthetic route that involves the use of synthetic intermediate generated for coupling with several nucleophiles containing the carbohydrate and 2H-pyrazole substituent moieties. All the compounds were screened against four tumor cell lines. Two of the compounds showed moderate cytotoxicity, while the other compounds strongly inhibit all tested cancer cell lines.