2-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-[(4-ethoxy-3-iodophenyl)amino]acrylamide | 846023-41-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-[(4-ethoxy-3-iodophenyl)amino]acrylamide
• 英文别名: 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-[(4-ethoxy-3-iodophenyl)amino]prop-2-enamide；2-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-(4-ethoxy-3-iodoanilino)prop-2-enamide
• CAS: 846023-41-4
• 化学式: C₁₉H₁₆Cl₂IN₃O₃
• 分子量: 532.165
• InChiKey: NMORNRUNTDMUNV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  28
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  83.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-[(4-ethoxy-3-iodophenyl)amino]acrylamide 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.25h， 生成 4-[(2,4-dichloro-5-methoxyphenyl)amino]-6-ethoxy-7-[4-(4-methylpiperazin-1-yl)but-1-ynyl]-3-quinolinecarbonitrile
  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：

  2-碘-4-硝基苯酚 在 铁粉 、 potassium carbonate 、 氯化铵 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 4.0h， 生成 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-[(4-ethoxy-3-iodophenyl)amino]acrylamide
  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

文献信息

• Process for preparation of 4-amino-3-quinolinecarbonitriles
  申请人：Sutherland Wiggins Karen

  公开号：US20050043537A1

  公开（公告）日：2005-02-24

  This invention discloses a process for the preparation of a 4-amino-3-quinolinecarbonitrile comprising combining an amine compound with a cyanoacetic acid and an acid catalyst to yield a cyanoacetamide; condensing the cyanoacetamide with an optionally up to tetra-substituted aniline in an alcoholic solvent and a trialkylorthoformate to yield a 3-amino-2-cyanoacrylamide; combining the 3-amino-2-cyanoacrylamide with phosphorus oxychloride in acetonitrile, butyronitrile, toluene or xylene, optionally in the presence of a catalyst to yield a 4-amino-3-quinolinecarbonitrile and also discloses a process for the preparation of a 7-amino-thieno[3,2-b]pyridine-6-carbonitrile comprising combining a disubstituted 3-amino thiophene with a cyanoacetamide and trialkylorthoformate in an alcoholic solvent to obtain a 3-amino-2-cyanoacrylamide; and combining the 3-amino-2-cyanoacrylamide with phosphorus oxychloride and acetonitrile, butyronitrile, toluene or xylene, optionally in the presence of a catalyst to yield a 7-amino-thieno[3,2-b]pyridine-6-carbonitrile and also discloses a process for the preparation of a 4-amino-3-quinolinecarbonitrile by combining an amine compound with a cyanoacetic acid and a peptide coupling reagent to obtain a suspension; filtering the suspension to yield a cyanoacetamide; condensing the cyanoacetamide with an optionally up to tetra-substituted aniline, an alcoholic solvent, and triethylorthoformate to yield a 3-amino-2-cyanoacrylamide; and combining the 3-amino-2-cyanoacrylamide with phosphorus oxychloride to yield a 4-amino-3-quinolinecarbonitrile.

  这项发明揭示了一种制备4-氨基-3-喹啉碳腈的过程，包括将胺化合物与氰乙酸和酸催化剂结合以产生氰乙酰胺；将氰乙酰胺与醇溶剂和三烷基正甲酸酯中的一个或多个取代苯胺缩合以产生3-氨基-2-氰基丙烯酰胺；将3-氨基-2-氰基丙烯酰胺与氯化磷在乙腈、丁腈、甲苯或二甲苯中结合，可选地在催化剂存在的情况下以产生4-氨基-3-喹啉碳腈，并且还揭示了一种制备7-氨基噻吩[3,2-b]吡啶-6-碳腈的过程，包括将二取代的3-氨基噻吩与氰乙酰胺和三烷基正甲酸酯在醇溶剂中结合以获得3-氨基-2-氰基丙烯酰胺；将3-氨基-2-氰基丙烯酰胺与氯化磷和乙腈、丁腈、甲苯或二甲苯结合，可选地在催化剂存在的情况下以产生7-氨基噻吩[3,2-b]吡啶-6-碳腈，并且还揭示了一种通过将胺化合物与氰乙酸和肽偶联试剂结合以获得悬浮液；过滤悬浮液以产生氰乙酰胺；将氰乙酰胺与一个或多个取代苯胺、醇溶剂和三乙基正甲酸酯缩合以产生3-氨基-2-氰基丙烯酰胺；将3-氨基-2-氰基丙烯酰胺与氯化磷结合以产生4-氨基-3-喹啉碳腈的制备过程。
• 4-[(2,4-Dichloro-5-methoxyphenyl)amino]-6-alkoxy-7-ethynyl-3-quinolinecarbonitriles for the treatment of ischemic injury
  申请人：Boschelli Harris Diane

  公开号：US20060116375A1

  公开（公告）日：2006-06-01

  Compounds of the formula: wherein: R is methyl or ethyl; R′ and R″ are independently alkyl of 1 to 3 carbon atoms, or R′ and R″, taken together with the nitrogen to which they are attached, can form a 5 or 6 membered saturated ring which may optionally contain an additional heteroatom selected from NR′″, O or S(O) n ; n is 0-2; and R′″ is hydrogen or alkyl of 1 to 3 carbon atoms, and pharmaceutically acceptable salts thereof, and their use for inhibiting vascular permeability caused by disease, injury or other trauma.

  该化合物的化学式为：其中：R为甲基或乙基；R′和R″分别是1至3个碳原子的烷基，或者R′和R″与它们所连接的氮原子一起形成一个5或6个成员的饱和环，该环可以选择性地包含一个来自NR′″、O或S（O）n的额外杂原子；n为0-2；R′″为氢或1至3个碳原子的烷基，以及其药学上可接受的盐，并且它们可用于抑制由疾病、损伤或其他创伤引起的血管通透性。
• WO2006/47262
  申请人：——

  公开号：——

  公开（公告）日：——