6-methoxy-8-(3-phthalimidopropylamino)-4-methyl-5-(3-trifluoromethylphenyloxy)-quinoline | 955995-50-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 6-methoxy-8-(3-phthalimidopropylamino)-4-methyl-5-(3-trifluoromethylphenyloxy)-quinoline
• 英文别名: 6-methoxy-8-(3-phthalimidopropylamino)-4-methyl-5-(3-trifluoromethylphenyloxy)quinoline；6-Methoxy-8-(3-phthalimidopropylamino)-4-methyl-5-(3-trifluoromethylphenyloxy) quinoline；2-[3-[[6-methoxy-4-methyl-5-[3-(trifluoromethyl)phenoxy]quinolin-8-yl]amino]propyl]isoindole-1,3-dione
• CAS: 955995-50-3
• 化学式: C₂₉H₂₄F₃N₃O₄
• 分子量: 535.522
• InChiKey: STCVLFVIZVRCJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  39
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  80.8
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  6-methoxy-8-(3-phthalimidopropylamino)-4-methyl-5-(3-trifluoromethylphenyloxy)-quinoline 在 肼 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 3.0h， 生成 6-methoxy-8-[(3-aminopropyl)amino]-4-methyl-5-(3-trifluoromethylphenyloxy)quinoline succinate
  参考文献：
  名称：

  WO2007/127930

  摘要：

  公开号：
• 作为产物：
  描述：

  2-(3-碘丙基)-1H-异吲哚-1,3(2H)-二酮 、 8-amino-6-methoxy-4-methyl-5-(3-trifluoromethylphenoxy)quinoline 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以72%的产率得到6-methoxy-8-(3-phthalimidopropylamino)-4-methyl-5-(3-trifluoromethylphenyloxy)-quinoline
  参考文献：
  名称：

  Synthesis and anti-breast cancer activities of substituted quinolines

  摘要：

  Promising anti-breast cancer agents derived from substituted quinolines were discovered. The quinolines were readily synthesized in a large scale from a sequence of reactions starting from 4-acetamidoanisole. The Michael addition product was isolated as the reaction intermediate in the ring closing reaction of 4-amino-5-nitro-2-(3-trifluoromethylphenyloxy) anisole with methyl vinyl ketone leading to 6-methoxy-4-methyl-8-nitro-5-(3-trifluoromethylphenyloxy) quinoline (14). The amino function of 8-amino-6-methoxy-4- methyl-5-(3-trifluoromethylphenyloxy) quinoline, prepared from 14, was connected to various side chains via alkylation with N( 3-iodopropyl) phthalimide, Michael addition with acrylonitrile, and reductive amination with various heterocycle carboxaldehydes, such as imidazole-4-carboxaldehyde, thiophene-2-carboxaldehyde, and 2-furaldehyde. Effects of the substituted quinolines on cell viability of T47D breast cancer cells using trypan blue exclusion assay were examined. The results showed that the IC50 value of 6-methoxy-8-[(2-furanylmethyl) amino]-4-methyl-5-(3-trifluoromethylphenyloxy) quinoline is 16 +/- 3 nM, the lowest IC50 out of all the quinolines tested. IC50 values of three other quinolines are in the nanomolar range, a desirable range for pharmacological testing. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.04.024

文献信息

• Compounds affecting gap junction activity
  申请人：Hua Duy H.

  公开号：US08809368B2

  公开（公告）日：2014-08-19

  This invention relates to novel quinoline compounds which affect gap junction activity. Also provided are methods of using such compounds and compositions containing the compounds to treat gap junction disorders.

  本发明涉及影响间隙连接活性的新奎奴啉化合物。还提供了使用这种化合物的方法和含有该化合物的组合物来治疗间隙连接障碍。
• COMPOUNDS AFFECTING GAP JUNCTION ACTIVITY
  申请人：HUA Duy H.

  公开号：US20090143425A1

  公开（公告）日：2009-06-04

  This invention relates to novel quinoline compounds which affect gap junction activity. Also provided are methods of using such compounds and compositions containing the compounds to treat gap junction disorders.

  本发明涉及新型喹啉化合物，其影响间隙连接活性。还提供了使用这种化合物的方法和含有这种化合物的组合物来治疗间隙连接障碍。
• US8809368B2
  申请人：——

  公开号：US8809368B2

  公开（公告）日：2014-08-19
• [EN] COMPOUNDS AFFECTING GAP JUNCTION ACTIVITY<br/>[FR] COMPOSÉS POUR INFLUENCER UNE ACTIVITÉ DE JONCTIONS LACUNAIRES
  申请人：UNIV KANSAS STATE

  公开号：WO2007127930A2

  公开（公告）日：2007-11-08

  [EN] ThThis invention relates to novel quinoline compounds which affect gap junction activity. Also provided are methods of using such compounds and compositions containing the compounds to treat gap junction disorders.
  [FR] La présente invention concerne de nouveaux composés de la quinoléine qui affectent l'activité des jonctions lacunaires. Elle concerne aussi des méthodes pour utiliser de tels composés et des compositions qui contiennent les composés pour traiter des troubles de jonctions lacunaires.
• Synthesis and anti-breast cancer activities of substituted quinolines
  作者：Aibin Shi、Thu A. Nguyen、Srinivas K. Battina、Sandeep Rana、Dolores J. Takemoto、Peter K. Chiang、Duy H. Hua

  DOI：10.1016/j.bmcl.2008.04.024

  日期：2008.6

  Promising anti-breast cancer agents derived from substituted quinolines were discovered. The quinolines were readily synthesized in a large scale from a sequence of reactions starting from 4-acetamidoanisole. The Michael addition product was isolated as the reaction intermediate in the ring closing reaction of 4-amino-5-nitro-2-(3-trifluoromethylphenyloxy) anisole with methyl vinyl ketone leading to 6-methoxy-4-methyl-8-nitro-5-(3-trifluoromethylphenyloxy) quinoline (14). The amino function of 8-amino-6-methoxy-4- methyl-5-(3-trifluoromethylphenyloxy) quinoline, prepared from 14, was connected to various side chains via alkylation with N( 3-iodopropyl) phthalimide, Michael addition with acrylonitrile, and reductive amination with various heterocycle carboxaldehydes, such as imidazole-4-carboxaldehyde, thiophene-2-carboxaldehyde, and 2-furaldehyde. Effects of the substituted quinolines on cell viability of T47D breast cancer cells using trypan blue exclusion assay were examined. The results showed that the IC50 value of 6-methoxy-8-[(2-furanylmethyl) amino]-4-methyl-5-(3-trifluoromethylphenyloxy) quinoline is 16 +/- 3 nM, the lowest IC50 out of all the quinolines tested. IC50 values of three other quinolines are in the nanomolar range, a desirable range for pharmacological testing. (C) 2008 Elsevier Ltd. All rights reserved.