N-(6-(4-(3-(3-chlorophenyl)ureido)phenyl)pyridin-2-yl)acrylamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: N-(6-(4-(3-(3-chlorophenyl)ureido)phenyl)pyridin-2-yl)acrylamide
• 英文别名: N-[6-[4-[(3-chlorophenyl)carbamoylamino]phenyl]pyridin-2-yl]prop-2-enamide
• 化学式: C₂₁H₁₇ClN₄O₂
• 分子量: 392.845
• InChiKey: XFYBEVQJFKVXIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  83.1
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  间氯苯异氰酸酯 在 四(三苯基膦)钯 、 potassium carbonate 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 0.5h， 生成 N-(6-(4-(3-(3-chlorophenyl)ureido)phenyl)pyridin-2-yl)acrylamide
  参考文献：
  名称：

  Discovery of novel anti-angiogenesis agents. Part 8: Diaryl thiourea bearing 1 H -indazole-3-amine as multi-target RTKs inhibitors

  摘要：

  VEGFR-2, TIE-2, and EphB4 are essential for both angiogenesis and tumorigenesis. Herein, we designed and prepared three classes of multi-target inhibitors based on the extensive sequence homology along the kinase domain of angiogenic RTKs. Biological evaluation indicated that these multi-target inhibitors exhibited considerable potential as novel anti-angiogeneic and anticancer agents. Among them, a diaryl thiourea bearing 1H-indazole-3-amine (16a) displayed the most potent RTK inhibition and excellent selectivity. It also showed inhibition on viability of human umbilical vein endothelial cells and anti proliferation against a broad spectrum of cancer cells. Therefore, 1H-indazole-3-amine could serve as a promising hinge binding group for multi-target inhibitors of VEGFR-2, Tie-2, and EphB4. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.10.008

文献信息

• 一种具有抗肿瘤活性的双芳基脲化合物及其 制备方法和应用
  申请人：西安交通大学

  公开号：CN106748991B

  公开（公告）日：2020-03-17

  本发明提供了一种具有抗肿瘤活性的双芳基脲化合物及其制备方法和应用，该化合物的结构式为其中R1为氢或卤素基团，R2为烷烃基团或卤素基团。该化合物对VEGFR‑2激酶有很好的抑制活性，能够通过抑制VEGFR‑2激酶的活性，阻断其诱导的信号通路，抑制肿瘤细胞的增生和迁移，从而可应用于抗肿瘤药物的制备。且该化合物的制备方法具有原料易得，反应条件温和，反应过程操作简单，所用试剂便宜的优点。
• Discovery of novel anti-angiogenesis agents. Part 8: Diaryl thiourea bearing 1 H -indazole-3-amine as multi-target RTKs inhibitors
  作者：Ying Sun、Yuanyuan Shan、Chuansheng Li、Ru Si、Xiaoyan Pan、Binghe Wang、Jie Zhang

  DOI：10.1016/j.ejmech.2017.10.008

  日期：2017.12

  VEGFR-2, TIE-2, and EphB4 are essential for both angiogenesis and tumorigenesis. Herein, we designed and prepared three classes of multi-target inhibitors based on the extensive sequence homology along the kinase domain of angiogenic RTKs. Biological evaluation indicated that these multi-target inhibitors exhibited considerable potential as novel anti-angiogeneic and anticancer agents. Among them, a diaryl thiourea bearing 1H-indazole-3-amine (16a) displayed the most potent RTK inhibition and excellent selectivity. It also showed inhibition on viability of human umbilical vein endothelial cells and anti proliferation against a broad spectrum of cancer cells. Therefore, 1H-indazole-3-amine could serve as a promising hinge binding group for multi-target inhibitors of VEGFR-2, Tie-2, and EphB4. (C) 2017 Elsevier Masson SAS. All rights reserved.