3-(4-fluorophenyl)-4,5a,6,7,8,9-hexahydro-1H,3H-pyrano[4,3-b]chromen-1-one | 1491165-67-3

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 3-(4-fluorophenyl)-4,5a,6,7,8,9-hexahydro-1H,3H-pyrano[4,3-b]chromen-1-one
• CAS: 1491165-67-3
• 化学式: C₁₈H₁₇FO₃
• 分子量: 300.33
• InChiKey: XCJMDUJBVVUPSI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.97
• 重原子数：
  22.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  35.53
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(4-fluorophenyl)-4,5a,6,7,8,9-hexahydro-1H,3H-pyrano[4,3-b]chromen-1-one 在 氧气 、 rose bengal 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以96%的产率得到3-(4-fluorophenyl)-3,4,6,7,8,9-hexahydro-4a,9a-epidioxypyrano[4,3-b]chromen-1(5aH)-one
  参考文献：
  名称：

  Design, synthesis, and in vitro cancer cell growth inhibition evaluation and antimalarial testing of trioxanes installed in cyclic 2-enoate substructures

  摘要：

  A novel series of 1,2,4-trioxanes were synthesized from 2H-pyrans via photooxidation, and their antiproliferative and growth factor inhibitory activity has been investigated across a variety of human cancer cell lines. Compounds 5k, 51, 5s, 7a and 7c exhibited the highest activity and selectivity against a human leukemia (MV4-11) cell line (IC50 = 0.5 mu M). Compound 5o showed the highest growth factor inhibitory activity against a melanoma (LOX-IMVI) cancer cell line (GI(50) = 1.0 mu M). A SAR study has confirmed the importance of the 1,2,4-trioxane unit as a pharmacophore for anticancer activity. The computer-assisted database analysis, COMPARE, has suggested that the compounds have unique mechanisms of actions that were different from those of known anticancer drugs. Some of the selected trioxanes were tested against the NF54 strain, albeit showing weak antiplasmodial activity. The molecular docking of trioxanes and hemin reveals that a short distance (130 angstrom) leads to their physical contact. The UV-vis spectroscopic analysis ensured the definite complexation between 1,2,4-trioxanes and hemin. The role of hemin-trioxane interaction in the hemin-induced oxidative damage has been studied using methylene blue as a substrate by UV-vis spectroscopy. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.008
• 作为产物：
  描述：

  1-cyclohexene-1-carboxaldehyde 、 6-(4-fluorophenyl)dihydro-2H-pyran-2,4(3H)-dione 在 乙二胺-N,N’-二乙酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 3-(4-fluorophenyl)-4,5a,6,7,8,9-hexahydro-1H,3H-pyrano[4,3-b]chromen-1-one
  参考文献：
  名称：

  Design, synthesis, and in vitro cancer cell growth inhibition evaluation and antimalarial testing of trioxanes installed in cyclic 2-enoate substructures

  摘要：

  A novel series of 1,2,4-trioxanes were synthesized from 2H-pyrans via photooxidation, and their antiproliferative and growth factor inhibitory activity has been investigated across a variety of human cancer cell lines. Compounds 5k, 51, 5s, 7a and 7c exhibited the highest activity and selectivity against a human leukemia (MV4-11) cell line (IC50 = 0.5 mu M). Compound 5o showed the highest growth factor inhibitory activity against a melanoma (LOX-IMVI) cancer cell line (GI(50) = 1.0 mu M). A SAR study has confirmed the importance of the 1,2,4-trioxane unit as a pharmacophore for anticancer activity. The computer-assisted database analysis, COMPARE, has suggested that the compounds have unique mechanisms of actions that were different from those of known anticancer drugs. Some of the selected trioxanes were tested against the NF54 strain, albeit showing weak antiplasmodial activity. The molecular docking of trioxanes and hemin reveals that a short distance (130 angstrom) leads to their physical contact. The UV-vis spectroscopic analysis ensured the definite complexation between 1,2,4-trioxanes and hemin. The role of hemin-trioxane interaction in the hemin-induced oxidative damage has been studied using methylene blue as a substrate by UV-vis spectroscopy. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.08.008