2-[(p-dimethylaminobenzylidene)hydrazinomethyl]-3-[4-(p-chlorophenyl)thiazol-2-yl]-6-bromoquinazolin-4-one | 935702-25-3

• 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: 2-[(p-dimethylaminobenzylidene)hydrazinomethyl]-3-[4-(p-chlorophenyl)thiazol-2-yl]-6-bromoquinazolin-4-one
• CAS: 935702-25-3
• 化学式: C₂₇H₂₂BrClN₆OS
• 分子量: 593.934
• InChiKey: FQZARDYIWUKPTJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.11
• 重原子数：
  37.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  75.41
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-[(p-dimethylaminobenzylidene)hydrazinomethyl]-3-[4-(p-chlorophenyl)thiazol-2-yl]-6-bromoquinazolin-4-one 、 巯基乙酸 在 zinc(II) chloride 作用下， 以 苯 为溶剂， 以51%的产率得到3-[[6-Bromo-3-[4-(4-chlorophenyl)-1,3-thiazol-2-yl]-4-oxoquinazolin-2-yl]methylamino]-2-[4-(dimethylamino)phenyl]-1,3-thiazolidin-4-one
  参考文献：
  名称：

  Synthesis of 3-[4′-(p-chlorophenyl)-thiazol-2′-yl]-2-[(substituted azetidinone/thiazolidinone)-aminomethyl]-6-bromoquinazolin-4-ones as anti-inflammatory agent

  摘要：

  N-Chloroacetyl-5-bromoanthranilic acid (1), 3-[4'-(p-chlorophenyl)-thiazol-2'-yl]-2-chloromethyl-6-bromoquinazolin-4-one (2), 3-[4'-(p-chlorophenyl)-thiazol-2'-yl]-2-hydrazinomethyl-6-bromoquinazolin-4-one (3), 3-[4'-(p-chlorophenyl)-thiazol-2'-yl]-2- substituted benzylidene aminomethyl-6-bromoquinazolin-4-ones (4-11), 2-[(4'-oxo-3'-chloro-2'-phenylazetidin-l'-yl)aminomethyl]-3 -[4"-(p-chlorophenyl)thiazo1-2"-yl]-6-bromoquinazolin-4-ones (12-19) and 2-(4'-oxo-2'-phenyl-thiazolidin-3'-yl-aminomethyl)3-[4"-(p-chlorophenyl)-thiazol-2"-yl]-6-bromoquinazolin-4-ones (20-27) have been synthesized. All the compounds have been screened for their anti-inflammatory and analgesic activities at the dose of 50 mg/kg po. Compound 21 showed maximum anti-inflammatory (38.35%) and analgesic (37.36%) activities. Compound 21 was also tested for ulcerogenic activity and the UD50 value was found to be 195.6 mg/kg po. The structure of all compounds has been evaluated by elemental analysis (C, H, N) and spectral analysis (IR, H-1 NMR and mass spectrometry). (c) 2007 Published by Elsevier.

  DOI：

  10.1016/j.bmc.2007.01.042
• 作为产物：
  描述：

  2-氨基-5-溴苯甲酸 在 吡啶 、 potassium carbonate 、 一水合肼 、 溶剂黄146 作用下， 以 乙醇 、 苯 为溶剂， 反应 17.0h， 生成 2-[(p-dimethylaminobenzylidene)hydrazinomethyl]-3-[4-(p-chlorophenyl)thiazol-2-yl]-6-bromoquinazolin-4-one
  参考文献：
  名称：

  Synthesis of 3-[4′-(p-chlorophenyl)-thiazol-2′-yl]-2-[(substituted azetidinone/thiazolidinone)-aminomethyl]-6-bromoquinazolin-4-ones as anti-inflammatory agent

  摘要：

  N-Chloroacetyl-5-bromoanthranilic acid (1), 3-[4'-(p-chlorophenyl)-thiazol-2'-yl]-2-chloromethyl-6-bromoquinazolin-4-one (2), 3-[4'-(p-chlorophenyl)-thiazol-2'-yl]-2-hydrazinomethyl-6-bromoquinazolin-4-one (3), 3-[4'-(p-chlorophenyl)-thiazol-2'-yl]-2- substituted benzylidene aminomethyl-6-bromoquinazolin-4-ones (4-11), 2-[(4'-oxo-3'-chloro-2'-phenylazetidin-l'-yl)aminomethyl]-3 -[4"-(p-chlorophenyl)thiazo1-2"-yl]-6-bromoquinazolin-4-ones (12-19) and 2-(4'-oxo-2'-phenyl-thiazolidin-3'-yl-aminomethyl)3-[4"-(p-chlorophenyl)-thiazol-2"-yl]-6-bromoquinazolin-4-ones (20-27) have been synthesized. All the compounds have been screened for their anti-inflammatory and analgesic activities at the dose of 50 mg/kg po. Compound 21 showed maximum anti-inflammatory (38.35%) and analgesic (37.36%) activities. Compound 21 was also tested for ulcerogenic activity and the UD50 value was found to be 195.6 mg/kg po. The structure of all compounds has been evaluated by elemental analysis (C, H, N) and spectral analysis (IR, H-1 NMR and mass spectrometry). (c) 2007 Published by Elsevier.

  DOI：

  10.1016/j.bmc.2007.01.042