2,4-dichloro-5-propoxyaniline | 380844-03-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2,4-dichloro-5-propoxyaniline
• CAS: 380844-03-1
• 化学式: C₉H₁₁Cl₂NO
• 分子量: 220.098
• InChiKey: FIUDAEISGGHCLE-UHFFFAOYSA-N

物化性质

• 沸点：
  317.9±37.0 °C(Predicted)
• 密度：
  1.274±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-氯-3-氰基-6,7-二甲氧基喹啉 、 2,4-dichloro-5-propoxyaniline 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以57%的产率得到4-Phenylamino-3-quinolinecarbonitrile deriv. 1e
  参考文献：
  名称：

  Optimization of 4-Phenylamino-3-quinolinecarbonitriles as Potent Inhibitors of Src Kinase Activity

  摘要：

  Subsequent to the discovery of 4-[(2,4-dichlorophenyl)amino]-6,7-dimethoxy-3-quinolinecarbonitrile (1a) as an inhibitor of Src kinase activity (IC50 = 30 nM), several additional analogues were prepared. Optimization of the C-4 anilino group of la led to le, which contains a 2,4-dichloro-5-methoxy-substituted aniline. Replacement of the methoxy group at C-7 of le with a 3-(morpholin-4-yl)propoxy group provided 2c, resulting in increased inhibition of both Src kinase activity and Src-mediated cell proliferation. Analogues of 2c, with other trisubstituted anilines at C-4 were also potent Src inhibitors, and the propoxy group of 2c was preferred over ethoxy, butoxy, or pentoxy. Replacement of the morpholine group of 2c with a 4-methylpiperazine group provided 31a, which had an IC50 of 1.2 nM in the Src enzymatic assay, an IC50 of 100 nM for the inhibition of Src-dependent cell proliferation and was selective for Src over non-Src family kinases. Compound 31a, which had higher 1 and 4 h plasma levels than 2c, effectively inhibited tumor growth in xenograft models.

  DOI：

  10.1021/jm0102250
• 作为产物：
  描述：

  N-(2,4-二氯-5-羟基苯基)乙酰胺 在 sodium hydroxide 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 7.0h， 生成 2,4-dichloro-5-propoxyaniline
  参考文献：
  名称：

  Optimization of 4-Phenylamino-3-quinolinecarbonitriles as Potent Inhibitors of Src Kinase Activity

  摘要：

  Subsequent to the discovery of 4-[(2,4-dichlorophenyl)amino]-6,7-dimethoxy-3-quinolinecarbonitrile (1a) as an inhibitor of Src kinase activity (IC50 = 30 nM), several additional analogues were prepared. Optimization of the C-4 anilino group of la led to le, which contains a 2,4-dichloro-5-methoxy-substituted aniline. Replacement of the methoxy group at C-7 of le with a 3-(morpholin-4-yl)propoxy group provided 2c, resulting in increased inhibition of both Src kinase activity and Src-mediated cell proliferation. Analogues of 2c, with other trisubstituted anilines at C-4 were also potent Src inhibitors, and the propoxy group of 2c was preferred over ethoxy, butoxy, or pentoxy. Replacement of the morpholine group of 2c with a 4-methylpiperazine group provided 31a, which had an IC50 of 1.2 nM in the Src enzymatic assay, an IC50 of 100 nM for the inhibition of Src-dependent cell proliferation and was selective for Src over non-Src family kinases. Compound 31a, which had higher 1 and 4 h plasma levels than 2c, effectively inhibited tumor growth in xenograft models.

  DOI：

  10.1021/jm0102250

文献信息

• EP0185731A4
  申请人：——

  公开号：EP0185731A4

  公开（公告）日：1988-11-02
• HERBICIDAL 2-ARYL-1,2,4-TRIAZINE-3,5(2H,4H)-DIONES AND SULFUR ANALOGS THEREOF
  申请人：FMC Corporation

  公开号：EP0185731A1

  公开（公告）日：1986-07-02
• [EN] HERBICIDAL 2-ARYL-1,2,4-TRIAZINE-3,5(2H,4H)-DIONES AND SULFUR ANALOGS THEREOF
  申请人：FMC CORPORATION

  公开号：WO1986000072A1

  公开（公告）日：1986-01-03

  (EN) Herbicidal 2-aryl-1,2,4-triazine-3,5(2H,4H)-Diones and analogous thiones, where W1 and W2 are oxygen on sulfur; R1 is amino, alkenyl, alkynyl, alkyl or substituted alkyl; R2 is hydrogen, alkenyl, alkynyl, amino, alkyl, substituted alkyl, halo, carboxyl or alkoxycarbonyl.(FR) 2-aryl-1,2,4-triazine-3,5(2H,4H)-diones et thiones analogues herbicides dans lesquelles W1 et W2 sont de l'oxygène sur du souffre; R1 est de l'amino, de l'alkényl, de l'alkynil, de l'alcoyle ou de l'alcoyle substitué; R2 est de l'hydrogène, de l'alkényl, de l'alkynil, de l'amino, de l'alcoyle ou de l'alcoyle substitué, de l'halo, du carboxyle ou de l'alcoxycarbonyle.