1-(4-(4-(pyrimidin-2-yl)piperazin-1-yl)phenyl)ethanone | 851631-13-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(4-(4-(pyrimidin-2-yl)piperazin-1-yl)phenyl)ethanone
• 英文别名: 1-[4-(4-Pyrimidin-2-ylpiperazin-1-yl)phenyl]ethanone
• CAS: 851631-13-5
• 化学式: C₁₆H₁₈N₄O
• 分子量: 282.345
• InChiKey: DUDHGQZWCBDSHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  49.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-吡啶甲醛 、 1-(4-(4-(pyrimidin-2-yl)piperazin-1-yl)phenyl)ethanone 在 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以36%的产率得到
  参考文献：
  名称：

  Design, Synthesis and Antitubercular Activity of Novel Isoniazid‑Cyclic‑Amine‑Azachalcones Hybrids

  摘要：

  In this work, it is described the design of twenty-four heterocyclic amine-azachalcones compounds through molecular hybridization of chalcone scaffold and fragments of isoniazid, fluoroquinolones, and linezolid with antituberculosis potential. The new compounds were synthesized via Claisen-Schmidt condensation, providing yields of 36-95%. Fifteen compounds showed antituberculosis activity against Mycobacterium tuberculosis H37Rv strain. Two amine-azachalcones 15 and 17 showed relevant biological activity with minimum inhibitory concentration (MIC) values of 6.62 and 4.85 mu M, respectively. Compound 12 showed the best profile of antitubercular activity with MIC = 9.54 mu M and selectivity index (SI) = 9.33. It was found that morpholine group is important to increase potency of antimycobacterial activity but also to add some toxicity to the chalcone molecular framework. The results described herein would be a guide in the designing of novel and optimized antitubercular derivatives based on the chalcone scaffold.

  DOI：

  10.21577/0103-5053.20200013
• 作为产物：
  描述：

  1-(2-嘧啶基)哌嗪 、 4-氟苯乙酮 在 potassium carbonate 作用下， 以 二甲基亚砜 为溶剂， 反应 48.0h， 以92%的产率得到1-(4-(4-(pyrimidin-2-yl)piperazin-1-yl)phenyl)ethanone
  参考文献：
  名称：

  Design, Synthesis and Antitubercular Activity of Novel Isoniazid‑Cyclic‑Amine‑Azachalcones Hybrids

  摘要：

  In this work, it is described the design of twenty-four heterocyclic amine-azachalcones compounds through molecular hybridization of chalcone scaffold and fragments of isoniazid, fluoroquinolones, and linezolid with antituberculosis potential. The new compounds were synthesized via Claisen-Schmidt condensation, providing yields of 36-95%. Fifteen compounds showed antituberculosis activity against Mycobacterium tuberculosis H37Rv strain. Two amine-azachalcones 15 and 17 showed relevant biological activity with minimum inhibitory concentration (MIC) values of 6.62 and 4.85 mu M, respectively. Compound 12 showed the best profile of antitubercular activity with MIC = 9.54 mu M and selectivity index (SI) = 9.33. It was found that morpholine group is important to increase potency of antimycobacterial activity but also to add some toxicity to the chalcone molecular framework. The results described herein would be a guide in the designing of novel and optimized antitubercular derivatives based on the chalcone scaffold.

  DOI：

  10.21577/0103-5053.20200013

文献信息

• Design, Synthesis and Antitubercular Activity of Novel Isoniazid‑Cyclic‑Amine‑Azachalcones Hybrids
  作者：Jefferson Oliveira、Cristiane Shiguemoto、Amarith das Neves、Flora Moreira、Giovana Gomes、Renata Perdomo、Sandro Barbosa、Palimécio Guerrero Jr.、Júlio Croda、Adriano Baroni

  DOI：10.21577/0103-5053.20200013

  日期：——

  In this work, it is described the design of twenty-four heterocyclic amine-azachalcones compounds through molecular hybridization of chalcone scaffold and fragments of isoniazid, fluoroquinolones, and linezolid with antituberculosis potential. The new compounds were synthesized via Claisen-Schmidt condensation, providing yields of 36-95%. Fifteen compounds showed antituberculosis activity against Mycobacterium tuberculosis H37Rv strain. Two amine-azachalcones 15 and 17 showed relevant biological activity with minimum inhibitory concentration (MIC) values of 6.62 and 4.85 mu M, respectively. Compound 12 showed the best profile of antitubercular activity with MIC = 9.54 mu M and selectivity index (SI) = 9.33. It was found that morpholine group is important to increase potency of antimycobacterial activity but also to add some toxicity to the chalcone molecular framework. The results described herein would be a guide in the designing of novel and optimized antitubercular derivatives based on the chalcone scaffold.