4-(cyclohexylamino)-5,6-benzocoumarin | 18420-75-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 4-(cyclohexylamino)-5,6-benzocoumarin
• 英文别名: 1-(cyclohexylamino)-3H-naphtho[2,1-b]pyran-3-one；3H-Naphtho[2,1-b]pyran-3-one, 1-(cyclohexylamino)-；1-(cyclohexylamino)benzo[f]chromen-3-one
• CAS: 18420-75-2
• 化学式: C₁₉H₁₉NO₂
• 分子量: 293.365
• InChiKey: BEXSHOZPOGVLPM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3H-萘并[2,1-b]吡喃-3-酮,1-羟基- 在 三乙胺 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 4-(cyclohexylamino)-5,6-benzocoumarin
  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

文献信息

• Chavda, Mausami; Shah, Anamik; Bhatt, Surendra, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2003, vol. 42, # 6, p. 1502 - 1507
  作者：Chavda, Mausami、Shah, Anamik、Bhatt, Surendra、Deo, Keshav、Kundu, Pareshnath

  DOI：——

  日期：——
• Pyran derivatives
  作者：Mario Di Braccio、Giancarlo Grossi、Giorgio Roma、Cristina Marzano、Franca Baccichetti、Morena Simonato、Franco Bordin

  DOI：10.1016/s0014-827x(03)00160-5

  日期：2003.11

  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).