2-chloro-5-ethoxy-4-methylaniline | 380844-08-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-chloro-5-ethoxy-4-methylaniline
• CAS: 380844-08-6
• 化学式: C₉H₁₂ClNO
• 分子量: 185.653
• InChiKey: GQYNMKMWAULXGL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  12
• 可旋转键数：
  2
• 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-chloro-5-ethoxy-4-methylaniline 在 吡啶盐酸盐 作用下， 以 乙二醇乙醚 为溶剂， 反应 3.0h， 以62%的产率得到4-(2-Chloro-5-ethoxy-4-methylanilino)-6,7-dimethoxyquinoline-3-carbonitrile
  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：

  4-chloro-2-methyl-5-nitro-phenol 在 盐酸 、 铁粉 、 potassium carbonate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 10.5h， 生成 2-chloro-5-ethoxy-4-methylaniline
  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

• AMIDE DERIVATIVE AND PHARMACEUTICAL COMPOSITION CONTAINING THE SAME
  申请人：Kato Shiro

  公开号：US20100249399A1

  公开（公告）日：2010-09-30

  Disclosed is a compound having a strong affinity to serotonin-4 receptors, which is useful as an enterokinesis-promoting agent or a digestive tract function-improving agent. Specifically, disclosed is a compound represented by Formula (1) or a pharmaceutically acceptable salt thereof. Also specifically disclosed is a pharmaceutical composition containing a compound represented by Formula (1) or a pharmaceutically acceptable salt thereof. [In Formula (1), Ar represents a group represented by Formula (Ar-1) or Formula (Ar-2).]

  揭示了一种具有强烈亲和力的化合物，对5-羟色胺-4受体具有亲和力，可用作促进肠动力或改善消化道功能的药剂。具体地，揭示了一种由化学式（1）表示的化合物或其药学上可接受的盐。还具体揭示了一种含有由化学式（1）表示的化合物或其药学上可接受的盐的药物组合物。【在化学式（1）中，Ar代表由化学式（Ar-1）或化学式（Ar-2）表示的基团。】
• US7906510B2
  申请人：——

  公开号：US7906510B2

  公开（公告）日：2011-03-15