1-(4-((diethylamino)methyl)phenyl)-3-(4-((3-ethynylphenyl)amino)quinazolin-6-yl)urea

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 1-(4-((diethylamino)methyl)phenyl)-3-(4-((3-ethynylphenyl)amino)quinazolin-6-yl)urea
• 英文别名: 1-[4-(Diethylaminomethyl)phenyl]-3-[4-(3-ethynylanilino)quinazolin-6-yl]urea；1-[4-(diethylaminomethyl)phenyl]-3-[4-(3-ethynylanilino)quinazolin-6-yl]urea
• 化学式: C₂₈H₂₈N₆O
• 分子量: 464.57
• InChiKey: KSNTXYJZCVBDNF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  82.2
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-乙氨基甲基苯甲酸 在 氯化亚砜 、 sodium azide 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 4.0h， 生成 1-(4-((diethylamino)methyl)phenyl)-3-(4-((3-ethynylphenyl)amino)quinazolin-6-yl)urea
  参考文献：
  名称：

  Combination of 4-anilinoquinazoline, arylurea and tertiary amine moiety to discover novel anticancer agents

  摘要：

  In present study, 4-anilinoquinazolines scaffold, arylurea and tertiary amine moiety were combined to design, synthesize gefitinib analogs and discover novel anticancer agents. A series of 4-anilinoquinazoline derivatives (1, 2, 3 and 4) bearing arylurea and tertiary amine moiety at its 6-position were synthesized. Their antiproliferative activities in vitro were evaluated via MTT assay against A431 cell and A549 cell. The SAR of the title compounds was discussed. The compounds 2d, 2i and 2j with potent antiproliferative activities were evaluated their inhibitory activity against EGFR-TK. Compound 2j displayed potent inhibitory activity against EGFR-TK. In addition, compound 2j, at 50 mg/kg, can completely inhibit cancer growth in established nude mouse A549 xenograft model in vivo. These results suggest that the 4-anilinoquinazoline derivatives bearing diarylurea and tertiary amino moiety at its 6-position can serve as anticancer agents and EGFR inhibitors. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.12.001

文献信息

• Combination of 4-anilinoquinazoline, arylurea and tertiary amine moiety to discover novel anticancer agents
  作者：Sai-Jie Zuo、Sai Zhang、Shuai Mao、Xiao-Xiao Xie、Xue Xiao、Min-Hnag Xin、Wei Xuan、Yuan-Yuan He、Yong-Xiao Cao、San-Qi Zhang

  DOI：10.1016/j.bmc.2015.12.001

  日期：2016.1

  In present study, 4-anilinoquinazolines scaffold, arylurea and tertiary amine moiety were combined to design, synthesize gefitinib analogs and discover novel anticancer agents. A series of 4-anilinoquinazoline derivatives (1, 2, 3 and 4) bearing arylurea and tertiary amine moiety at its 6-position were synthesized. Their antiproliferative activities in vitro were evaluated via MTT assay against A431 cell and A549 cell. The SAR of the title compounds was discussed. The compounds 2d, 2i and 2j with potent antiproliferative activities were evaluated their inhibitory activity against EGFR-TK. Compound 2j displayed potent inhibitory activity against EGFR-TK. In addition, compound 2j, at 50 mg/kg, can completely inhibit cancer growth in established nude mouse A549 xenograft model in vivo. These results suggest that the 4-anilinoquinazoline derivatives bearing diarylurea and tertiary amino moiety at its 6-position can serve as anticancer agents and EGFR inhibitors. (C) 2015 Elsevier Ltd. All rights reserved.