6-(methylthio)-8H-1,3-dioxolo[4,5-g][1]benzopyran-8-one | 681806-37-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 6-(methylthio)-8H-1,3-dioxolo[4,5-g][1]benzopyran-8-one
• 英文别名: 6-methylsulfanyl-[1,3]dioxolo[4,5-g]chromen-8-one
• CAS: 681806-37-1
• 化学式: C₁₁H₈O₄S
• 分子量: 236.248
• InChiKey: FYNVDRXRNBRZDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.24
• 重原子数：
  16.0
• 可旋转键数：
  1.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  48.67
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  苯胺 、 6-(methylthio)-8H-1,3-dioxolo[4,5-g][1]benzopyran-8-one 在 对甲苯磺酸 作用下， 以 乙二醇 为溶剂， 反应 4.0h， 以45%的产率得到6-(phenylamino)-8H-1,3-dioxolo[4,5-g][1]benzopyran-8-one
  参考文献：
  名称：

  Pyran derivatives

  摘要：

  The N-substituted tricyclic 2-aminochromone derivatives 1a, 2a, and 2b were obtained by treating the corresponding (methylthio) or (methylsulfinyl) derivatives 10, 11, or 12, respectively, with an excess of the proper amines. Compound 2c was synthesized through the reaction of 2-naphthol with the ethyl N,N-diphenylmalonamate/POCl(3) reagent 14. The N-substituted 4-aminocoumarin bicyclic and tricyclic derivatives 5-8 were prepared by treating the corresponding chloro derivatives with the excess suitable amines. Compounds 1, 2, 5-8 were tested in vitro for their antiproliferative activity (DNA synthesis inhibition in Ehrlich cells) and cytotoxicity (MTT test in HeLa cells). The inhibitory properties of three selected compounds (5c, 5e, 7c) on protein and RNA syntheses in Ehrlich cells were also evaluated. Among the 27 compounds tested, 10 4-aminocoumarin derivatives (5-8) and two 2-aminochromone derivatives (1a and 2a) showed an appreciable antiproliferative activity (IC(50) range: 1.74-13.8 microM), whereas only four compounds 5-8 exhibited a comparable cytotoxic activity (IC(50) range: 4.95-12.9 microM).

  DOI：

  10.1016/s0014-827x(03)00160-5
• 作为产物：
  描述：

  1-(6-hydroxybenzo[d][1,3]dioxol-5-yl)ethan-1-one 在 potassium tert-butylate 、 potassium carbonate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 1.0h， 生成 6-(methylthio)-8H-1,3-dioxolo[4,5-g][1]benzopyran-8-one
  参考文献：
  名称：

  Pyran derivatives

  摘要：

  The N-substituted tricyclic 2-aminochromone derivatives 1a, 2a, and 2b were obtained by treating the corresponding (methylthio) or (methylsulfinyl) derivatives 10, 11, or 12, respectively, with an excess of the proper amines. Compound 2c was synthesized through the reaction of 2-naphthol with the ethyl N,N-diphenylmalonamate/POCl(3) reagent 14. The N-substituted 4-aminocoumarin bicyclic and tricyclic derivatives 5-8 were prepared by treating the corresponding chloro derivatives with the excess suitable amines. Compounds 1, 2, 5-8 were tested in vitro for their antiproliferative activity (DNA synthesis inhibition in Ehrlich cells) and cytotoxicity (MTT test in HeLa cells). The inhibitory properties of three selected compounds (5c, 5e, 7c) on protein and RNA syntheses in Ehrlich cells were also evaluated. Among the 27 compounds tested, 10 4-aminocoumarin derivatives (5-8) and two 2-aminochromone derivatives (1a and 2a) showed an appreciable antiproliferative activity (IC(50) range: 1.74-13.8 microM), whereas only four compounds 5-8 exhibited a comparable cytotoxic activity (IC(50) range: 4.95-12.9 microM).

  DOI：

  10.1016/s0014-827x(03)00160-5