8-Amino-3-fluorobenzo[c]chromen-6-one | 179898-14-7

• 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-Amino-3-fluorobenzo[c]chromen-6-one
• CAS: 179898-14-7
• 化学式: C₁₃H₈FNO₂
• 分子量: 229.21
• InChiKey: VPVKIFJYJZPOBW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-Amino-3-fluorobenzo[c]chromen-6-one 在 三乙基硅烷 、 正丁基锂 、 三氟化硼乙醚 、 碘 作用下， 以 二氯甲烷 为溶剂， 反应 39.0h， 生成 5-(4-Chloro-phenyl)-8-fluoro-2,2,4-trimethyl-2,5-dihydro-1H-6-oxa-1-aza-chrysene
  参考文献：
  名称：

  5-Aryl-1,2-dihydro-5H-chromeno[3,4-f]quinolines as Potent, Orally Active, Nonsteroidal Progesterone Receptor Agonists:  The Effect of D-Ring Substituents

  摘要：

  Several 5-(4-chlorophenyl)-1,2-dihydro-5H-chromeno[3,4-f]quinolines were prepared to determine the effects of substitution at C(8) and C(9) on the progestational activity of this pharmacophore. In combination with a halogen (F or Cl) at C(9), replacement of the C(5) aryl group with variously substituted aryl groups resulted in optimization of the progestational activity, affording compounds with in vitro activity greater than that of progesterone as measured by a cotransfection assay using human progesterone receptor subtype-B (hPR-B). Binding affinities (K-i) to hPR-A were subnanomolar in many cases. These in vitro effects were verified in vivo using a rodent model. Compound 10 (LG120794, 9-chloro-5-(4-chlorophenyl)-1,2-dihydro-2,2,4-trimethyl-5H-chromeno[3,4-f]quinoline] was more potent than medroxyprogesterone acetate at counterpoising the effects of estradiol benzoate in the uterine wet weight assay using immature rats.

  DOI：

  10.1021/jm9705770
• 作为产物：
  描述：

  4-fluoro-2-methoxyphenylboronic acid 在 palladium on activated charcoal 四(三苯基膦)钯 、 三氯化铝 、 氯化亚砜 、 氢气 、 sodium carbonate 、 溶剂黄146 作用下， 以 乙酸乙酯 、 1,2-二氯乙烷 为溶剂， 反应 19.67h， 生成 8-Amino-3-fluorobenzo[c]chromen-6-one
  参考文献：
  名称：

  5-Aryl-1,2-dihydro-5H-chromeno[3,4-f]quinolines as Potent, Orally Active, Nonsteroidal Progesterone Receptor Agonists:  The Effect of D-Ring Substituents

  摘要：

  Several 5-(4-chlorophenyl)-1,2-dihydro-5H-chromeno[3,4-f]quinolines were prepared to determine the effects of substitution at C(8) and C(9) on the progestational activity of this pharmacophore. In combination with a halogen (F or Cl) at C(9), replacement of the C(5) aryl group with variously substituted aryl groups resulted in optimization of the progestational activity, affording compounds with in vitro activity greater than that of progesterone as measured by a cotransfection assay using human progesterone receptor subtype-B (hPR-B). Binding affinities (K-i) to hPR-A were subnanomolar in many cases. These in vitro effects were verified in vivo using a rodent model. Compound 10 (LG120794, 9-chloro-5-(4-chlorophenyl)-1,2-dihydro-2,2,4-trimethyl-5H-chromeno[3,4-f]quinoline] was more potent than medroxyprogesterone acetate at counterpoising the effects of estradiol benzoate in the uterine wet weight assay using immature rats.

  DOI：

  10.1021/jm9705770