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.
• Optimization of 4-Phenylamino-3-quinolinecarbonitriles as Potent Inhibitors of Src Kinase Activity
  作者：Diane H. Boschelli、Fei Ye、Yanong D. Wang、Minu Dutia、Steve L. Johnson、Biqi Wu、Karen Miller、Dennis W. Powell、Deanna Yaczko、Mairead Young、Mark Tischler、Kim Arndt、Carolyn Discafani、Carlo Etienne、Jay Gibbons、Janet Grod、Judy Lucas、Jennifer M. Weber、Frank Boschelli

  DOI：10.1021/jm0102250

  日期：2001.11.1

  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.