8-chloro-6H-1,3-dioxolo[4,5-g][1]benzopyran-6-one | 147806-38-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 8-chloro-6H-1,3-dioxolo[4,5-g][1]benzopyran-6-one
• 英文别名: 4-chloroayapin；8-Chloro-[1,3]dioxolo[4,5-g]chromen-6-one
• CAS: 147806-38-0
• 化学式: C₁₀H₅ClO₄
• 分子量: 224.6
• InChiKey: ZQBFBHKKEPMSRL-UHFFFAOYSA-N

物化性质

• 熔点：
  188-189 °C(Solv: ethyl acetate (141-78-6))
• 沸点：
  389.5±42.0 °C(Predicted)
• 密度：
  1.63±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-chloro-6H-1,3-dioxolo[4,5-g][1]benzopyran-6-one 在 溶剂黄146 、 锌 作用下， 反应 0.5h， 以48%的产率得到[1,3]二氧杂环戊并[4,5-g]苯并吡喃-6-酮
  参考文献：
  名称：

  Soman, Shubhangi S.; Trivedi, K. N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 3, p. 372 - 373

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(6-hydroxybenzo[d][1,3]dioxol-5-yl)ethan-1-one 在 sodium 、 三氯氧磷 作用下， 反应 11.0h， 生成 8-chloro-6H-1,3-dioxolo[4,5-g][1]benzopyran-6-one
  参考文献：
  名称：

  Soman, Shubhangi S.; Trivedi, K. N., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 3, p. 372 - 373

  摘要：

  DOI：

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).