2-bromo-1-(2,4-dichloro-5-fluorophenyl)-3-phenylprop-2-en-1-one | 948583-60-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 2-bromo-1-(2,4-dichloro-5-fluorophenyl)-3-phenylprop-2-en-1-one
• CAS: 948583-60-6
• 化学式: C₁₅H₈BrCl₂FO
• 分子量: 374.036
• InChiKey: JTHZJQXULMHZJF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.75
• 重原子数：
  20.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  N1-[5-(4-amino-5-sulfanyl-4H-1,2,4-triazol-3-yl)-4-methyl-2-thienyl]-2-chloroacetamide 、 2-bromo-1-(2,4-dichloro-5-fluorophenyl)-3-phenylprop-2-en-1-one 在 氢氧化钾 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 以81%的产率得到N-[5-[(7Z)-7-benzylidene-6-(2,4-dichloro-5-fluorophenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-3-yl]-4-methylthiophen-2-yl]-2-chloroacetamide
  参考文献：
  名称：

  A novel approach to cyclin-dependent kinase 5/p25 inhibitors: A potential treatment for Alzheimer’s disease

  摘要：

  Based on the earlier results of our in-house database and compound library, a series of novel clubbed thienyl triazoles was designed which may emerge as potential cdk5/p25 inhibitors, for the treatment of Alzheimer's disease. A benign synthesis was planned so as to take an advantage of MAOS (Microwave Assisted Organic Synthesis) method. Evaluation of the SAR of this series has allowed the identification of compounds 4, 5, 7 and 8 from series I while 13, 14, 16 and 17 from series 11 as significant cdk5/p25 inhibitors and thus have potential as possible treatments for Alzheimer's disease. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.06.053
• 作为产物：
  描述：

  2,3-dibromo-1-(2,4-dichloro-5-fluorophenyl)-3-phenylpropan-1-one 在 三乙胺 作用下， 以 苯 为溶剂， 生成 2-bromo-1-(2,4-dichloro-5-fluorophenyl)-3-phenylprop-2-en-1-one
  参考文献：
  名称：

  Analgesic and antimicrobial studies of some 2,4-dichloro-5-fluorophenyl containing arylidenetriazolothiadiazines

  摘要：

  2,4-Dichloro-5-fluorophenyl containing 7-arylidenetriazolothiadiazines were obtained by the reaction of 4-amino-3-(2,4-dichloro-5-fluorophenyl)-5-mercapto-1,2,4-triazole with 2,3-dibromo-1,3-diarylpropan-1-ones, and also by the reaction of 4-amino-3-(2,4-dichloro-5-fluorophenyl)-5-mercapto-1,2,4-triazole with alpha-bromopropenones in the presence of a base. The structure of the 7-arylidenetriazolothiadiazines was confirmed by an alternative synthesis. A plausible mechanism for the formation of 7-arylidenetriazolothiadiazines is proposed. All newly synthesized compounds were screened for their analgesic and antimicrobial activities. Compounds bearing 4-chlorophenyl or 3,4-methylenedioxyphenyl moieties at position 7 of the arylidenetriazolothiadiazines showed excellent analgesic activity. Arylidenetriazolothiadiazines carrying a phenyl, 4-chlorophenyl, 4-methylphenyl, 3,4-dimethoxyphenyl, and 2,4-dichlorophenyl moieties at position 7 showed excellent antibacterial and antifungal activities.

  DOI：

  10.1007/s00706-007-0797-9