6-Bromo-2-[[2-(2,6-dichloroanilino)phenyl]methyl]-3-[4-[[4-(diethylamino)-2-hydroxyphenyl]methylideneamino]phenyl]quinazolin-4-one | 1111775-90-6

• 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: 6-Bromo-2-[[2-(2,6-dichloroanilino)phenyl]methyl]-3-[4-[[4-(diethylamino)-2-hydroxyphenyl]methylideneamino]phenyl]quinazolin-4-one
• CAS: 1111775-90-6
• 化学式: C₃₈H₃₂BrCl₂N₅O₂
• 分子量: 741.514
• InChiKey: SGMLMDAUMINWJT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  48
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  80.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-Bromo-2-[[2-(2,6-dichloroanilino)phenyl]methyl]-3-[4-[[4-(diethylamino)-2-hydroxyphenyl]methylideneamino]phenyl]quinazolin-4-one 、 氯乙酰氯 在 三乙胺 作用下， 以 1,4-二氧六环 为溶剂， 以67%的产率得到6-Bromo-3-[4-[3-chloro-2-[4-(diethylamino)-2-hydroxyphenyl]-4-oxoazetidin-1-yl]phenyl]-2-[[2-(2,6-dichloroanilino)phenyl]methyl]quinazolin-4-one
  参考文献：
  名称：

  Synthesis and antimicrobial activities of 2-azetidinyl-4-quinazolinone derivatives of diclofenac analogue

  摘要：

  A new class of 2-azetidinyl-4-quinazolinones 6a-k was synthesized by multi-step process, starting from 2-[2-(2,6-dichlorophenyl)amino]phenyl acetic acid 1. Acid 1 was easily converted to acid chloride 2, which on cyclization reaction with 5-bromo anthranilic acid yielded benzoxazinone 3. The condensation reaction of 3 with benzene-1,4-diamine afforded 4-quinazolinone 4. Finally the title compound 6a-k was synthesized from 4-quinazolinone 4 by Schiff base formation 5a-k with aromatic aldehyde and then cyclization reaction with chloroacetylchloride. The in vitro antimicrobial activity of compounds 5a-k and 6a-k were tested. These compounds showed pronounced antimicrobial activity when 4-Cl and 4-OCH (3) groups were present.

  DOI：

  10.1007/s00044-010-9345-y
• 作为产物：
  描述：

  双氯芬酸 在 吡啶 、 氯化亚砜 、 溶剂黄146 作用下， 以 乙醇 、 苯 为溶剂， 反应 2.0h， 生成 6-Bromo-2-[[2-(2,6-dichloroanilino)phenyl]methyl]-3-[4-[[4-(diethylamino)-2-hydroxyphenyl]methylideneamino]phenyl]quinazolin-4-one
  参考文献：
  名称：

  Synthesis and antimicrobial activities of 2-azetidinyl-4-quinazolinone derivatives of diclofenac analogue

  摘要：

  A new class of 2-azetidinyl-4-quinazolinones 6a-k was synthesized by multi-step process, starting from 2-[2-(2,6-dichlorophenyl)amino]phenyl acetic acid 1. Acid 1 was easily converted to acid chloride 2, which on cyclization reaction with 5-bromo anthranilic acid yielded benzoxazinone 3. The condensation reaction of 3 with benzene-1,4-diamine afforded 4-quinazolinone 4. Finally the title compound 6a-k was synthesized from 4-quinazolinone 4 by Schiff base formation 5a-k with aromatic aldehyde and then cyclization reaction with chloroacetylchloride. The in vitro antimicrobial activity of compounds 5a-k and 6a-k were tested. These compounds showed pronounced antimicrobial activity when 4-Cl and 4-OCH (3) groups were present.

  DOI：

  10.1007/s00044-010-9345-y