4-(4-aminophenylthio)-N-cyclohexylpicolinamide | 1417344-67-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-(4-aminophenylthio)-N-cyclohexylpicolinamide
• CAS: 1417344-67-2
• 化学式: C₁₈H₂₁N₃OS
• 分子量: 327.45
• InChiKey: GRUIXQGUHYDSHI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  68.01
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-(4-aminophenylthio)-N-cyclohexylpicolinamide 、 4-氯-3-三氟甲基硫氰酸苯酯 以 二氯甲烷 为溶剂， 反应 22.0h， 以71.7%的产率得到4-(4-(3-(4-chloro-3-(trifluoromethyl)phenyl)thioureido)phenylthio)-N-cyclohexylpicolinamide
  参考文献：
  名称：

  Thiourea and thioether derivatives of sorafenib: synthesis, crystal structure, and antiproliferative activity

  摘要：

  A series of novel sorafenib derivatives containing diaryl thiourea and thioether, 9a-u, was designed and synthesized, and their antiproliferative activities against HCT116 and MDA-MB-231 cell lines were also evaluated and described. Most compounds exhibited potent antiproliferative activity against HCT116 cells with IC50 = 1.8-80.4 mu M. Compounds 9p, 9r, and 9s demonstrated competitive antiproliferative activities to sorafenib, against all two cancer cell lines. The structures of all the newly synthesized compounds were determined by H-1 NMR, C-13 NMR, and HRMS, and compound 9n was characterized by single-crystal X-ray diffraction. Primary structure-activity relationships (SAR) have also been established.

  DOI：

  10.1007/s00044-012-0400-8
• 作为产物：
  描述：

  2-吡啶甲酸 在 光气 、 potassium tert-butylate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 4-(4-aminophenylthio)-N-cyclohexylpicolinamide
  参考文献：
  名称：

  Thiourea and thioether derivatives of sorafenib: synthesis, crystal structure, and antiproliferative activity

  摘要：

  A series of novel sorafenib derivatives containing diaryl thiourea and thioether, 9a-u, was designed and synthesized, and their antiproliferative activities against HCT116 and MDA-MB-231 cell lines were also evaluated and described. Most compounds exhibited potent antiproliferative activity against HCT116 cells with IC50 = 1.8-80.4 mu M. Compounds 9p, 9r, and 9s demonstrated competitive antiproliferative activities to sorafenib, against all two cancer cell lines. The structures of all the newly synthesized compounds were determined by H-1 NMR, C-13 NMR, and HRMS, and compound 9n was characterized by single-crystal X-ray diffraction. Primary structure-activity relationships (SAR) have also been established.

  DOI：

  10.1007/s00044-012-0400-8