4-Methoxy-10-methyl-2H-naphtho<2,3-b>pyran-2-thione | 219561-78-1

• 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: 4-Methoxy-10-methyl-2H-naphtho<2,3-b>pyran-2-thione
• CAS: 219561-78-1
• 化学式: C₁₅H₁₂O₂S
• 分子量: 256.325
• InChiKey: YJWYEBCCUYEYPF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.63
• 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：
  0.13
• 拓扑面积：
  22.37
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  4-Methoxy-10-methyl-2H-naphtho<2,3-b>pyran-2-thione 在 吡啶盐酸盐 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 1.08h， 生成 10-Methyl-2-(methylthio)-4H-naphtho<2,3-b>pyran-4-one
  参考文献：
  名称：

  Pyran derivatives XX. 2-Aminochromone benzo-fused derivatives with antiproliferative properties

  摘要：

  The N-substituted 2-aminochromones 1 and their benzo-fused derivatives 2-4 described herein were mostly prepared by treating the corresponding (methylthio) derivatives 10-13 with an excess of the proper amines. Only the morpholino derivatives 3d and 4c were obtained from the reaction of the ethyl 3-morpholino-3-oxopropanoate/POCl3 reagent with 1-naphthol or 1-methyl-2-naphthol, respectively. The amino derivatives 1-4, as well as their methylthio analogues 10-13, were tested in vitro for their inhibitory activity on the infectivity of T2 bacteriophage, on the macromolecular synthesis in Ehrlich cells and on the clonal growth capacity of HeLa cells. Several of the angular or linear aminonaphthopyranones 2 and 3 or 4, respectively, and the (methylthio) derivatives 10, 11 and 13 induced a significant inhibition of DNA synthesis, but usually a clearly lower inhibition of clonal growth. Only the Linear 2-amino-10-methyl-4H-naphtho [2,3-b]pyran-4-ones 4a and 4b significantly inhibited the clonal growth in HeLa cells and T2 bacteriophage infectivity, respectively. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00055-x
• 作为产物：
  描述：

  1-甲基萘-2-醇 在 劳森试剂 、 sodium methylate 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 14.0h， 生成 4-Methoxy-10-methyl-2H-naphtho<2,3-b>pyran-2-thione
  参考文献：
  名称：

  Pyran derivatives XX. 2-Aminochromone benzo-fused derivatives with antiproliferative properties

  摘要：

  The N-substituted 2-aminochromones 1 and their benzo-fused derivatives 2-4 described herein were mostly prepared by treating the corresponding (methylthio) derivatives 10-13 with an excess of the proper amines. Only the morpholino derivatives 3d and 4c were obtained from the reaction of the ethyl 3-morpholino-3-oxopropanoate/POCl3 reagent with 1-naphthol or 1-methyl-2-naphthol, respectively. The amino derivatives 1-4, as well as their methylthio analogues 10-13, were tested in vitro for their inhibitory activity on the infectivity of T2 bacteriophage, on the macromolecular synthesis in Ehrlich cells and on the clonal growth capacity of HeLa cells. Several of the angular or linear aminonaphthopyranones 2 and 3 or 4, respectively, and the (methylthio) derivatives 10, 11 and 13 induced a significant inhibition of DNA synthesis, but usually a clearly lower inhibition of clonal growth. Only the Linear 2-amino-10-methyl-4H-naphtho [2,3-b]pyran-4-ones 4a and 4b significantly inhibited the clonal growth in HeLa cells and T2 bacteriophage infectivity, respectively. (C) 1998 Elsevier Science S.A. All rights reserved.

  DOI：

  10.1016/s0014-827x(98)00055-x