2-chloromethyl-3-methylnaphtho[1,2-b]furan-4,5-dione | 1617512-12-5

• 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: 2-chloromethyl-3-methylnaphtho[1,2-b]furan-4,5-dione
• CAS: 1617512-12-5
• 化学式: C₁₄H₉ClO₃
• 分子量: 260.677
• InChiKey: AWCTWXODGAYSGE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.37
• 重原子数：
  18.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  47.28
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-chloromethyl-3-methylnaphtho[1,2-b]furan-4,5-dione 在 NADPH 、 NAD(P)H:quinone oxidoreductase-1 、 potassium carbonate 、 potassium iodide 作用下， 以 aq. phosphate buffer 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.08h， 生成
  参考文献：
  名称：

  2-Substituted 3-methylnaphtho[1,2-b]furan-4,5-diones as novel L-shaped ortho-quinone substrates for NAD(P)H:quinone oxidoreductase (NQO1)

  摘要：

  A series of L-shaped ortho-quinone analogs were designed by analyzing the binding mode with NQO1. Metabolic studies demonstrated that compounds 2m, 2n and 2q exhibited higher metabolic rates than beta-lapachone. The docking studies, which supported the rationalization of the metabolic studies, constituted a prospective rational basis for the development of optimized ortho-quinone analogs. Besides, good substrates (2m, 2n and 2r) for NQO1 showed higher selective toxicity than beta-lapachone toward A549 (NQO1-rich) cancer cells versus H596 (NQO1-deficient) cells. Determination of superoxide (O-2(center dot-)) production and in vitro cytotoxicity evaluation in the presence of the NQO1 inhibitor dicoumarol confirmed that the ortho-quinones exerted their antitumor activity through NQO1-mediated ROS production by redox cycling. It was suggested that the L-shaped quinone substrates for NQO1 possessed better specificity and safety than beta-lapachone. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.041
• 作为产物：
  描述：

  3-methyl-2-morpholino-2,3-dihydronaphtho[1,2-b]furan-5-ol 在 盐酸 、 potassium dihydrogenphosphate 作用下， 以 四氢呋喃 、 水 、 乙酸乙酯 、 丙酮 为溶剂， 反应 19.0h， 生成 2-chloromethyl-3-methylnaphtho[1,2-b]furan-4,5-dione
  参考文献：
  名称：

  2-Substituted 3-methylnaphtho[1,2-b]furan-4,5-diones as novel L-shaped ortho-quinone substrates for NAD(P)H:quinone oxidoreductase (NQO1)

  摘要：

  A series of L-shaped ortho-quinone analogs were designed by analyzing the binding mode with NQO1. Metabolic studies demonstrated that compounds 2m, 2n and 2q exhibited higher metabolic rates than beta-lapachone. The docking studies, which supported the rationalization of the metabolic studies, constituted a prospective rational basis for the development of optimized ortho-quinone analogs. Besides, good substrates (2m, 2n and 2r) for NQO1 showed higher selective toxicity than beta-lapachone toward A549 (NQO1-rich) cancer cells versus H596 (NQO1-deficient) cells. Determination of superoxide (O-2(center dot-)) production and in vitro cytotoxicity evaluation in the presence of the NQO1 inhibitor dicoumarol confirmed that the ortho-quinones exerted their antitumor activity through NQO1-mediated ROS production by redox cycling. It was suggested that the L-shaped quinone substrates for NQO1 possessed better specificity and safety than beta-lapachone. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.05.041