(S,E)-N-(4-((3-chlorophenyl)amino)quinazolin-6-yl)-1-(5-(4-methoxybenzylidene)-4-oxo-4,5-dihydrothiazol-2-yl)pyrrolidine-2-carboxamide

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S,E)-N-(4-((3-chlorophenyl)amino)quinazolin-6-yl)-1-(5-(4-methoxybenzylidene)-4-oxo-4,5-dihydrothiazol-2-yl)pyrrolidine-2-carboxamide
• 英文别名: (2S)-N-[4-(3-chloroanilino)quinazolin-6-yl]-1-[(5E)-5-[(4-methoxyphenyl)methylidene]-4-oxo-1,3-thiazol-2-yl]pyrrolidine-2-carboxamide
• 化学式: C₃₀H₂₅ClN₆O₃S
• 分子量: 585.086
• InChiKey: QUOXDJAMDRVEPI-MDQJKVKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  41
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-硫代-5-(4-甲氧基苄亚基)噻唑烷-4-酮 在 吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 乙醇 为溶剂， 反应 32.0h， 生成 (S,E)-N-(4-((3-chlorophenyl)amino)quinazolin-6-yl)-1-(5-(4-methoxybenzylidene)-4-oxo-4,5-dihydrothiazol-2-yl)pyrrolidine-2-carboxamide
  参考文献：
  名称：

  Combination of 4-anilinoquinazoline and rhodanine as novel epidermal growth factor receptor tyrosine kinase inhibitors

  摘要：

  A type of novel rhodanine-based 4-anilinoquinazoline, which designed the combination between quinazoline as the backbone and various substituted biological rhodanine groups as the side chain, have been synthesized, and their antiproliferative activities were also evaluated firstly. These compounds displayed good antiproliferative activity and EGFR-TK inhibitory activity. Among them, compound 8d showed good inhibitory activity (IC50 = 2.7 mu M for Hep G2, IC50 = 3.1 mu M for A549) and molecular docking of 8d into EGFR TK active site was also performed, this inhibitor well fitting the active site might well explain its excellent inhibitory activity. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.04.065

文献信息

• Combination of 4-anilinoquinazoline and rhodanine as novel epidermal growth factor receptor tyrosine kinase inhibitors
  作者：Si-Ning Li、Yun-Yun Xu、Jia-Yu Gao、Hong-ran Yin、Shi-Lei Zhang、Huan-Qiu Li

  DOI：10.1016/j.bmc.2015.04.065

  日期：2015.7

  A type of novel rhodanine-based 4-anilinoquinazoline, which designed the combination between quinazoline as the backbone and various substituted biological rhodanine groups as the side chain, have been synthesized, and their antiproliferative activities were also evaluated firstly. These compounds displayed good antiproliferative activity and EGFR-TK inhibitory activity. Among them, compound 8d showed good inhibitory activity (IC50 = 2.7 mu M for Hep G2, IC50 = 3.1 mu M for A549) and molecular docking of 8d into EGFR TK active site was also performed, this inhibitor well fitting the active site might well explain its excellent inhibitory activity. (C) 2015 Elsevier Ltd. All rights reserved.