3-cyano-6-methoxy-4-[(3,4,5-trimethoxyphenyl)amino]quinolin-7-yl trifluoromethanesulfonate | 907191-66-6

• 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: 3-cyano-6-methoxy-4-[(3,4,5-trimethoxyphenyl)amino]quinolin-7-yl trifluoromethanesulfonate
• 英文别名: 3-Cyano-6-methoxy-4-[(3,4,5-trimethoxyphenyl)amino]quinolin-7-yl trifluoromethanesulfonate；[3-cyano-6-methoxy-4-(3,4,5-trimethoxyanilino)quinolin-7-yl] trifluoromethanesulfonate
• CAS: 907191-66-6
• 化学式: C₂₁H₁₈F₃N₃O₇S
• 分子量: 513.451
• InChiKey: PEHJOEKRMNJTRS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  35
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  137
• 氢给体数：
  1
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  3-cyano-6-methoxy-4-[(3,4,5-trimethoxyphenyl)amino]quinolin-7-yl trifluoromethanesulfonate 、 1-(3-丁炔-1-基)-4-甲基哌嗪 在 三乙胺 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三苯基膦 作用下， 以 N-甲基吡咯烷酮 为溶剂， 反应 4.0h， 生成 6-Methoxy-7-(4-(4-methylpiperazin-1-yl)but-1-ynyl)-4-(3,4,5-trimethoxyphenylamino)quinoline-3-carbonitrile
  参考文献：
  名称：

  Inhibition of Src kinase activity by 7-ethynyl-4-phenylamino-3-quinolinecarbonitriles: Identification of SKS-927

  摘要：

  Of a series of 7-ethynyl-3-quinolinecarbonitriles, the most potent Src inhibitory activity was observed with 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[4-(4-methylpiperazin-1-yl)but-1-ynyl]-3-quinolinecarbonitrile (SKS-927). Variation of the solubilizing amine tail or removal of the methoxy group from either C-6 of the quinoline core or C-5 of the aniline headpiece led to reduced activity. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.11.077
• 作为产物：
  描述：

  3,4,5-三甲氧基苯胺 、 (4-chloro-3-cyano-6-methoxy-7-quinolyl)trifluoromethanesulfonate 在 吡啶盐酸盐 作用下， 以 乙二醇乙醚 为溶剂， 生成 3-cyano-6-methoxy-4-[(3,4,5-trimethoxyphenyl)amino]quinolin-7-yl trifluoromethanesulfonate
  参考文献：
  名称：

  Further studies on ethenyl and ethynyl-4-phenylamino-3-quinolinecarbonitriles: identification of a subnanomolar Src kinase inhibitor

  摘要：

  Several new ethynyl- and ethenyl-4-phenylamino-3-quinolinecarbonitriles were synthesized and tested for Src inhibition. Derivatives bearing an ethenyl or ethynyl substituent at C-6 showed decreased Src inhibitory activity. Incorporation of an ethenylpyridine N-oxide group at C-7 provided 20b, a 0.6 nM inhibitor of Src enzymatic activity with excellent cellular potency. (c) 2005 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2005.01.004

文献信息

• PREPARATION OF 7-ALKENYL-3 QUINOLINECARBONITRILES VIA A PALLADIUM MEDIATED COUPLING REACTION
  申请人：Wang Yanong Daniel

  公开号：US20090099356A1

  公开（公告）日：2009-04-16

  The present invention is directed to a process for preparing compounds of formula (I): wherein A, R 1 -R 3 , X, s, t, u, m and Z are defined herein, comprising the step of reacting a reagent of formula (II): in the presence of Pd(O) metal with a compound of formula (III): or salts thereof. Another aspect of this invention is a method of preparing compounds of formula (VI).

  本发明涉及一种制备化合物的方法，其化学式如下（I）：其中A、R1-R3、X、s、t、u、m和Z在此处定义，包括以下步骤：在Pd（O）金属存在下，将化学式（II）的试剂与化学式（III）的化合物或其盐反应。本发明的另一个方面是制备化合物的方法，其化学式为（VI）。
• 7-(Aryl/heteroaryl-2-ylethynyl)-4-phenylamino-3-quinolinecarbonitriles as new Src kinase inhibitors: Addition of water solubilizing groups
  作者：Biqi Wu、Ana Carolina Barrios Sosa、Diane H. Boschelli、Frank Boschelli、Erick E. Honores、Jennifer M. Golas、Dennis W. Powell、Yanong D. Wang

  DOI：10.1016/j.bmcl.2006.05.015

  日期：2006.8

  necarbonitriles with a 7-ethynyl group substituted by a pyridine, phenyl or thiophene ring containing basic water solubilizing groups were prepared and evaluated as Src kinase inhibitors. Of these new analogs, potent activity was observed with compounds having a (2,4-dichloro-5-methoxyphenyl)amino group at C-4, a methoxy or ethoxy group at C-6, and a pyridyl group bearing a dimethylamine or N-methylpiperazine

  制备具有被含碱性水增溶基团的吡啶，苯基或噻吩环取代的7-乙炔基的新的4-苯基氨基-3-喹啉甲腈，并将其评价为Src激酶抑制剂。在这些新的类似物中，观察到具有在C-4具有（2,4-二氯-5-甲氧基苯基）氨基，在C-6具有甲氧基或乙氧基以及带有二甲胺或N的吡啶基的化合物的有效活性。 -甲基哌嗪在C-7的乙炔基上。
• Further studies on ethenyl and ethynyl-4-phenylamino-3-quinolinecarbonitriles: identification of a subnanomolar Src kinase inhibitor
  作者：Ana Carolina Barrios Sosa、Diane H. Boschelli、Biqi Wu、Yan Wang、Jennifer M. Golas

  DOI：10.1016/j.bmcl.2005.01.004

  日期：2005.3

  Several new ethynyl- and ethenyl-4-phenylamino-3-quinolinecarbonitriles were synthesized and tested for Src inhibition. Derivatives bearing an ethenyl or ethynyl substituent at C-6 showed decreased Src inhibitory activity. Incorporation of an ethenylpyridine N-oxide group at C-7 provided 20b, a 0.6 nM inhibitor of Src enzymatic activity with excellent cellular potency. (c) 2005 Published by Elsevier Ltd.
• Inhibition of Src kinase activity by 7-ethynyl-4-phenylamino-3-quinolinecarbonitriles: Identification of SKS-927
  作者：Diane H. Boschelli、Ana Carolina Barrios Sosa、Jennifer M. Golas、Frank Boschelli

  DOI：10.1016/j.bmcl.2006.11.077

  日期：2007.3

  Of a series of 7-ethynyl-3-quinolinecarbonitriles, the most potent Src inhibitory activity was observed with 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-methoxy-7-[4-(4-methylpiperazin-1-yl)but-1-ynyl]-3-quinolinecarbonitrile (SKS-927). Variation of the solubilizing amine tail or removal of the methoxy group from either C-6 of the quinoline core or C-5 of the aniline headpiece led to reduced activity. (c) 2006 Elsevier Ltd. All rights reserved.