(4-(3-aminophenoxy)pyridin-2-yl)(pyrrolidin-1-yl)methanone | 1412891-71-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4-(3-aminophenoxy)pyridin-2-yl)(pyrrolidin-1-yl)methanone
• 英文别名: [4-(3-Aminophenoxy)pyridin-2-yl]-pyrrolidin-1-ylmethanone；[4-(3-aminophenoxy)pyridin-2-yl]-pyrrolidin-1-ylmethanone
• CAS: 1412891-71-4
• 化学式: C₁₆H₁₇N₃O₂
• 分子量: 283.33
• InChiKey: ZCRPZFAQNOCKJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  68.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4-(3-aminophenoxy)pyridin-2-yl)(pyrrolidin-1-yl)methanone 、 异硫氰酸-4-(三氟甲氧基)苯酯 以 二氯甲烷 为溶剂， 反应 18.0h， 以77%的产率得到1-(3-((2-(pyrrolidine-1-carbonyl)pyridin-4-yl)oxy)phenyl)-3-(4-(trifluoromethoxy)phenyl)thiourea
  参考文献：
  名称：

  Design, synthesis and biological activities of sorafenib derivatives as antitumor agents

  摘要：

  A series of novel sorafenib derivatives, 9a-w, was designed and synthesized in high yields using various substituted anilines, and their antiproliferative activities against HCT116, PC-3 and MDA-MB-231 cell lines were also evaluated and described. All compounds exhibited potent antiproliferative activity against HCT116 and PC-3 cells with IC50 = 2.8-52.0 and 2.2-45.6 mu M; compounds 9p and 9q demonstrated competitive antiproliferative activities to sorafenib against all three cancer cell lines, the cytotoxicity of compound 9r is more potent than that of sorafenib. Compounds (9g, 9p, 9q and 9r) were chosen for further evaluation of the anti-angiogenesis activity, and showed the inhibition of sprout formation from aortic ring ex vivo. The structures of all the newly synthesized compounds were determined by H-1 NMR, C-13 NMR and HRMS. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.031
• 作为产物：
  描述：

  4-氯吡啶-2-甲酸甲酯 在 potassium tert-butylate 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 (4-(3-aminophenoxy)pyridin-2-yl)(pyrrolidin-1-yl)methanone
  参考文献：
  名称：

  Design, synthesis and biological activities of sorafenib derivatives as antitumor agents

  摘要：

  A series of novel sorafenib derivatives, 9a-w, was designed and synthesized in high yields using various substituted anilines, and their antiproliferative activities against HCT116, PC-3 and MDA-MB-231 cell lines were also evaluated and described. All compounds exhibited potent antiproliferative activity against HCT116 and PC-3 cells with IC50 = 2.8-52.0 and 2.2-45.6 mu M; compounds 9p and 9q demonstrated competitive antiproliferative activities to sorafenib against all three cancer cell lines, the cytotoxicity of compound 9r is more potent than that of sorafenib. Compounds (9g, 9p, 9q and 9r) were chosen for further evaluation of the anti-angiogenesis activity, and showed the inhibition of sprout formation from aortic ring ex vivo. The structures of all the newly synthesized compounds were determined by H-1 NMR, C-13 NMR and HRMS. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.09.031