9-chloro-3,3-dimethyl-6-(40-fluoro-phenyl)-2,4,6-trihydro-(5H)-benzothiazolo[2,3-b]quinazolin-5-one | 1450756-40-7

• 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: 9-chloro-3,3-dimethyl-6-(40-fluoro-phenyl)-2,4,6-trihydro-(5H)-benzothiazolo[2,3-b]quinazolin-5-one
• CAS: 1450756-40-7
• 化学式: C₂₂H₁₈ClFN₂OS
• 分子量: 412.915
• InChiKey: GYBSQAUWDWIAGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.15
• 重原子数：
  28.0
• 可旋转键数：
  1.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  32.67
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为产物：
  描述：

  2-氨基-6-氯苯并噻唑 、 对氟苯甲醛 、 5,5-二甲基-1,3-环己二酮 在 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate 作用下， 反应 0.05h， 以90%的产率得到9-chloro-3,3-dimethyl-6-(40-fluoro-phenyl)-2,4,6-trihydro-(5H)-benzothiazolo[2,3-b]quinazolin-5-one
  参考文献：
  名称：

  Greener synthesis and photo-antiproliferative activity of novel fluorinated benzothiazolo[2, 3-b]quinazolines

  摘要：

  1-Butyl-3-methylimidazolium and inorganic anions such as BF4(-), PF6(-) and PTSA(-) are used as green catalyst and reaction medium for synthesis of fluorinated benzothiazolo[2,3-b]quinazoline-2H-ones analogues via one-pot reaction of 2-amino-6-chlorobenzothiazole (1), fluorinated aldehydes (2) dimedone and (3) using microwave irradiation. The whole procedure is simple and straightforward, and no aqueous work-up is needed. Synthesized compounds are screened for photo-antiproliferative activity against human keratinocytes cell line and carcinoma cell lines like promyelocytic leukemia (HL-60) cells and adenocarcinoma (LoVo) cells. Structure activity relationship studies revealed that the substitution on aryl ring played a dominant role and was responsible for the antiproliferative activity.

  DOI：

  10.1007/s00044-013-0689-y