[5-(4-ethoxy-3-methoxyphenyl)-3-(4-hydroxyphenyl)-4,5-dihydropyrazol-1-yl]pyridin-3-yl-methanone | 1098021-26-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: [5-(4-ethoxy-3-methoxyphenyl)-3-(4-hydroxyphenyl)-4,5-dihydropyrazol-1-yl]pyridin-3-yl-methanone
• 英文别名: CY5；[3-(4-Ethoxy-3-methoxyphenyl)-5-(4-hydroxyphenyl)-3,4-dihydropyrazol-2-yl]-pyridin-3-ylmethanone
• CAS: 1098021-26-1
• 化学式: C₂₄H₂₃N₃O₄
• 分子量: 417.464
• InChiKey: OTUDAOUIVLEAJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-吡啶甲酰肼 、 3-(4-ethoxy-3-methoxyphenyl)-1-(4-hydroxyphenyl)propenone 以 正丁醇 为溶剂， 反应 24.0h， 以95%的产率得到[5-(4-ethoxy-3-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

文献信息

• Pharmacophore based discovery of potential antimalarial agent targeting haem detoxification pathway
  作者：Badri Narayan Acharya、Deepika Saraswat、Mahabir Parshad Kaushik

  DOI：10.1016/j.ejmech.2008.02.005

  日期：2008.12

  Pharmacophore hypotheses were generated from molecules having putative antimalarial activities targeting haem detoxification pathway of malarial parasite. A training set consisting of 33 compounds, whose activities were evaluated for haem polymerization inhibition and against chloroquine resistant (K1) strain of Plasmodium falciparum, was optimized to generate hypotheses. The hypothesis showing optimum correlation between actual and estimated activities was validated by Fischer's randomization test at 95% confidence level and used as a model to screen our in-house compound database. Nicotinic acid [trans-3-(4-ethoxy-3-methoxy-phenyl)-1-(4-hydroxy-phenyl)-allylidene]-hydrazide (ALH5) was obtained as a hit. The compound was synthesized and evaluated against chloroquine sensitive (MRC-02) and resistant (RKL9) strains of malarial parasite P. falciparum. The compound showed antimalarial activity in nanomolar range and was found comparable with chloroquine. (C) 2008 Elsevier Masson SAS. All rights reserved.