3-(5-bromo-2-methoxyphenyl)-1-(4-hydroxyphenyl)propenone | 571932-00-8

• 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: 3-(5-bromo-2-methoxyphenyl)-1-(4-hydroxyphenyl)propenone
• 英文别名: 4'-hydroxy-5-bromo-2-methoxychalcone；3-(5-Bromo-2-methoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one
• CAS: 571932-00-8
• 化学式: C₁₆H₁₃BrO₃
• 分子量: 333.181
• InChiKey: ORCQJAUSIVGUQM-UHFFFAOYSA-N

物化性质

• 沸点：
  499.3±45.0 °C(Predicted)
• 密度：
  1.458±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-吡啶甲酰肼 、 3-(5-bromo-2-methoxyphenyl)-1-(4-hydroxyphenyl)propenone 以 正丁醇 为溶剂， 反应 18.0h， 以96%的产率得到[5-(5-bromo-2-methoxyphenyl)-3-(4-hydroxyphenyl)-4,5-dihydropyrazol-1-yl]pyridin-3-yl-methanone
  参考文献：
  名称：

  Synthesis and antimalarial evaluation of 1, 3, 5-trisubstituted pyrazolines

  摘要：

  A series of 1,3,5-trisubstituted pyrazolines were synthesized and evaluated for in vitro antimalarial efficacy against chloroquine sensitive (MRC-02) as well as chloroquine resistant (RKL9) strains of Plasmodium falciparum. The activity was at nano molar concentration. beta-hematin formation inhibition activity (BHIA(50)) of the pyrazolines were determined and correlated with antimalarial activity. A reasonably good correlation (r = 0.62) was observed between antimalarial activity (IC50) and BHIA(50). This suggests that antimalarial mode of action of this class of compounds appears to be similar to that of chloroquine and involves the inhibition of hemozoin formation. Some of the compounds were showing better antimalarial activity than chloroquine against resistant strain of P. falciparum and were also found active in the in vivo experiment. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.10.023
• 作为产物：
  描述：

  5-溴-2-甲氧基苯甲醛 、 对羟基苯乙酮 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 24.17h， 以60%的产率得到3-(5-bromo-2-methoxyphenyl)-1-(4-hydroxyphenyl)propenone
  参考文献：
  名称：

  Synthesis and antimalarial evaluation of 1, 3, 5-trisubstituted pyrazolines

  摘要：

  A series of 1,3,5-trisubstituted pyrazolines were synthesized and evaluated for in vitro antimalarial efficacy against chloroquine sensitive (MRC-02) as well as chloroquine resistant (RKL9) strains of Plasmodium falciparum. The activity was at nano molar concentration. beta-hematin formation inhibition activity (BHIA(50)) of the pyrazolines were determined and correlated with antimalarial activity. A reasonably good correlation (r = 0.62) was observed between antimalarial activity (IC50) and BHIA(50). This suggests that antimalarial mode of action of this class of compounds appears to be similar to that of chloroquine and involves the inhibition of hemozoin formation. Some of the compounds were showing better antimalarial activity than chloroquine against resistant strain of P. falciparum and were also found active in the in vivo experiment. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.10.023

文献信息

• 含查尔酮的芳氧羧酸酯类化合物的合成方法及其在农药上的应用
  申请人：江苏大学

  公开号：CN110041198B

  公开（公告）日：2022-03-22

  本发明属于除草剂技术领域，具体提供了一种含查尔酮的芳氧羧酸酯类化合物的合成方法及其在农药上的应用，合成步骤如下：适当温度下，按比例将4‑羟基查尔酮衍生物与芳氧乙酰氯加入到适当反应溶剂中，加入适当催化剂，进行反应，反应完成后，除去溶剂，向残余物中加入NaOH溶液，过滤、洗涤、干燥，重结晶即得含查尔酮的芳氧羧酸酯类化合物。本发明提供了一种简单、有效的方法合成含查尔酮的芳氧羧酸酯类化合物，且本发明的化合物具有较强的除草活性。
• Synthesis and antimalarial evaluation of 1, 3, 5-trisubstituted pyrazolines
  作者：Badri Narayan Acharya、Deepika Saraswat、Mugdha Tiwari、Asish Kumar Shrivastava、Ramarao Ghorpade、Saroj Bapna、Mahabir Parshad Kaushik

  DOI：10.1016/j.ejmech.2009.10.023

  日期：2010.2

  A series of 1,3,5-trisubstituted pyrazolines were synthesized and evaluated for in vitro antimalarial efficacy against chloroquine sensitive (MRC-02) as well as chloroquine resistant (RKL9) strains of Plasmodium falciparum. The activity was at nano molar concentration. beta-hematin formation inhibition activity (BHIA(50)) of the pyrazolines were determined and correlated with antimalarial activity. A reasonably good correlation (r = 0.62) was observed between antimalarial activity (IC50) and BHIA(50). This suggests that antimalarial mode of action of this class of compounds appears to be similar to that of chloroquine and involves the inhibition of hemozoin formation. Some of the compounds were showing better antimalarial activity than chloroquine against resistant strain of P. falciparum and were also found active in the in vivo experiment. (C) 2009 Elsevier Masson SAS. All rights reserved.