2-(1,2-dihydroxypropan-2-yl)-5-methoxy-11-methyl-1,11-dihydrobenzofuro[4,5-b][1,8]naphthyridin-6(2H)-one | 1334911-25-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(1,2-dihydroxypropan-2-yl)-5-methoxy-11-methyl-1,11-dihydrobenzofuro[4,5-b][1,8]naphthyridin-6(2H)-one
• CAS: 1334911-25-9
• 化学式: C₁₉H₂₀N₂O₅
• 分子量: 356.378
• InChiKey: IRSLEIKQOBPSRT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.14
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  93.81
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-(1,2-dihydroxypropan-2-yl)-5-methoxy-11-methyl-1,11-dihydrobenzofuro[4,5-b][1,8]naphthyridin-6(2H)-one 在 吡啶 、 咪唑 、 4-二甲氨基吡啶 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成
  参考文献：
  名称：

  Design, synthesis and anticancer activity of novel dihydrobenzofuro[4,5-b][1,8]naphthyridin-6-one derivatives

  摘要：

  On the basis of the chemical structures of psorospermin with a xanthone template and acronycine derivatives with an acridone template, rac-1 and rac-2 constructed on an 1,2-dihydrobenzofuro[4,5-b] [1,8] naphthyridin-6(11H)-one scaffold were designed and synthesized as potential anticancer agents. Their anticancer activities were evaluated against five human cancer cell lines. Rac-2 showed similar anticancer activity to doxorubicin and rac-1 exhibited even higher anticancer activity against LNCaP (IC50 = 0.14 mu M), DU145 ( IC50 = 0.15 mu M), PC3 ( IC50 = 0.30 mu M) and MCF-7 ( IC50 = 0.26 mu M) cancer lines than doxorubicin and rac-2. Also, rac-1 revealed very potent anticancer activity ( IC50 = 0.15 mu M) against MCF-7/ADR cell (doxorubicin-resistant breast cancer cell) lines and induced G2/M phase arrest of the cell cycle in MCF-7/ADR cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.016
• 作为产物：
  描述：

  5-methoxy-11-methyl-2-(prop-1-en-2-yl)-1,11-dihydrobenzofuro[4,5-b][1,8]naphthyridin-6(2H)-one 在 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 水 、 丙酮 为溶剂， 生成 2-(1,2-dihydroxypropan-2-yl)-5-methoxy-11-methyl-1,11-dihydrobenzofuro[4,5-b][1,8]naphthyridin-6(2H)-one
  参考文献：
  名称：

  Design, synthesis and anticancer activity of novel dihydrobenzofuro[4,5-b][1,8]naphthyridin-6-one derivatives

  摘要：

  On the basis of the chemical structures of psorospermin with a xanthone template and acronycine derivatives with an acridone template, rac-1 and rac-2 constructed on an 1,2-dihydrobenzofuro[4,5-b] [1,8] naphthyridin-6(11H)-one scaffold were designed and synthesized as potential anticancer agents. Their anticancer activities were evaluated against five human cancer cell lines. Rac-2 showed similar anticancer activity to doxorubicin and rac-1 exhibited even higher anticancer activity against LNCaP (IC50 = 0.14 mu M), DU145 ( IC50 = 0.15 mu M), PC3 ( IC50 = 0.30 mu M) and MCF-7 ( IC50 = 0.26 mu M) cancer lines than doxorubicin and rac-2. Also, rac-1 revealed very potent anticancer activity ( IC50 = 0.15 mu M) against MCF-7/ADR cell (doxorubicin-resistant breast cancer cell) lines and induced G2/M phase arrest of the cell cycle in MCF-7/ADR cells. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.016