2-Methoxy-8-nitro-benzo[c]chromen-6-one | 179898-40-9

• 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: 2-Methoxy-8-nitro-benzo[c]chromen-6-one
• 英文别名: 2-Methoxy-8-nitrobenzo[c]chromen-6-one
• CAS: 179898-40-9
• 化学式: C₁₄H₉NO₅
• 分子量: 271.229
• InChiKey: IISMAKSLLQEKLC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  81.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-Methoxy-8-nitro-benzo[c]chromen-6-one 在 tin(ll) chloride 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以95%的产率得到8-Amino-2-methoxy-benzo[c]chromen-6-one
  参考文献：
  名称：

  Development of progesterone receptor antagonists from 1,2-dihydrochromeno[3,4-f]quinoline agonist pharmacophore

  摘要：

  A series of 1,2-dihydrochromeno[3,4-f]quinoline derivatives was synthesized and tested in biological assays to evaluate the nonsteroidal progesterone receptor modulator pharmacophore (4) as antiprogestins. A number of potent analogues were identified by modification of the substituents at the D-ring. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00256-7
• 作为产物：
  描述：

  2-溴-5-硝基苯甲酸甲酯 在 sodium hydroxide 、 四(三苯基膦)钯 、 sodium hydride 、 sodium carbonate 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 22.0h， 生成 2-Methoxy-8-nitro-benzo[c]chromen-6-one
  参考文献：
  名称：

  Development of progesterone receptor antagonists from 1,2-dihydrochromeno[3,4-f]quinoline agonist pharmacophore

  摘要：

  A series of 1,2-dihydrochromeno[3,4-f]quinoline derivatives was synthesized and tested in biological assays to evaluate the nonsteroidal progesterone receptor modulator pharmacophore (4) as antiprogestins. A number of potent analogues were identified by modification of the substituents at the D-ring. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00256-7

文献信息

• 5-Aryl-1,2-dihydro-5<i>H</i>-chromeno[3,4-<i>f</i>]quinolines as Potent, Orally Active, Nonsteroidal Progesterone Receptor Agonists:  The Effect of D-Ring Substituents
  作者：James P. Edwards、Sarah J. West、Keith B. Marschke、Dale E. Mais、Marco M. Gottardis、Todd K. Jones

  DOI：10.1021/jm9705770

  日期：1998.1.1

  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.
• Development of progesterone receptor antagonists from 1,2-dihydrochromeno[3,4-f]quinoline agonist pharmacophore
  作者：Lin Zhi、Josef D Ringgenberg、James P Edwards、Christopher M Tegley、Sarah J West、Barbara Pio、Mehrnouch Motamedi、Todd K Jones、Keith B Marschke、Dale E Mais、William T Schrader

  DOI：10.1016/s0960-894x(03)00256-7

  日期：2003.6

  A series of 1,2-dihydrochromeno[3,4-f]quinoline derivatives was synthesized and tested in biological assays to evaluate the nonsteroidal progesterone receptor modulator pharmacophore (4) as antiprogestins. A number of potent analogues were identified by modification of the substituents at the D-ring. (C) 2003 Elsevier Science Ltd. All rights reserved.