4-Chloro-10-methyl-2H-naphtho<2,3-b>pyran-2-one | 68884-71-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异香豆素及其衍生物
• 英文名称: 4-Chloro-10-methyl-2H-naphtho<2,3-b>pyran-2-one
• 英文别名: 4-chloro-10-methyl-benzo[g]chromen-2-one；2-Oxo-4-chlor-10-methyl-2H-naphtho-pyran；4-chloro-10-methylbenzo[g]chromen-2-one
• CAS: 68884-71-9
• 化学式: C₁₄H₉ClO₂
• 分子量: 244.677
• InChiKey: HHKJZZKKGSVHTN-UHFFFAOYSA-N

物化性质

• 熔点：
  178-179 °C(Solv: benzene (71-43-2))
• 沸点：
  428.7±45.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  17.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  30.21
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-Chloro-10-methyl-2H-naphtho<2,3-b>pyran-2-one 在 劳森试剂 、 sodium methylate 、 吡啶盐酸盐 、 potassium carbonate 作用下， 以 丙酮 、 甲苯 为溶剂， 反应 4.58h， 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：

  4-吗啉丙酸 b-氧代-乙酯 、 1-甲基萘-2-醇 在 三氯氧磷 作用下， 生成 4-Chloro-10-methyl-2H-naphtho<2,3-b>pyran-2-one 、 10-Methyl-4-morpholino-2H-naphtho<2,3-b>pyran-2-one 、 10-Methyl-2-morpholino-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

文献信息

• Coumarin, chromone, and 4(3H)-pyrimidinone novel bicyclic and tricyclic derivatives as antiplatelet agents: synthesis, biological evaluation, and comparative molecular field analysis
  作者：Giorgio Roma、Mario Di Braccio、Antonio Carrieri、Giancarlo Grossi、Giuliana Leoncini、Maria Grazia Signorello、Angelo Carotti

  DOI：10.1016/s0968-0896(02)00307-3

  日期：2003.1

  As a further part of our chemical and biological studies in this field, we describe the multistep preparations of the properly substituted 2-(1-piperazinyl)chromone 1b, 4-(1-piperazinyl)coumarins 5c-h, their linear benzo-fused analogues 4a,b and 8a,b, bicyclic (15e-g) and tricyclic (15h,i) fused derivatives of 6-(1-piperazinyl)pyrimidin-4(3H)-one, and of the 4H-pyrido[1,2-a]pyrimidine derivatives 9b

  作为我们在该领域化学和生物学研究的另一部分，我们描述了正确取代的2-（1-哌嗪基）色酮1b，4-（1-哌嗪基）香豆素5c-h及其线性苯并稠合的多步制备方法类似物4a，b和8a，b，6-（1-哌嗪基）嘧啶-4（3H）-one和4H-吡啶基的双环（15e-g）和三环（15h，i）稠合衍生物[1， 2-a]嘧啶衍生物9b，c。体外评估ADP，胶原蛋白或Ca（2+）离子载体A23187在富含血小板的血浆中诱导的对人血小板聚集的抑制特性显示化合物5d-g和15f，g，i的高活性依此顺序，香豆素5g和5d被证明是最有效的体外抗血小板药。因此，为了也考虑4-氨基香豆素的结构分类，
• 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).