3-(4-fluorophenyl)-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazole | 1252008-05-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(4-fluorophenyl)-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazole
• CAS: 1252008-05-1
• 化学式: C₁₈H₁₉FN₂O₃
• 分子量: 330.359
• InChiKey: CZMISEXUHUYNBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  52.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(4-氟苯基)-3-(3,4,5-三甲氧基苯基)-2-丙烯-1-酮 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以74%的产率得到3-(4-fluorophenyl)-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  Synthesis and in vitro antitumor activity of new 4,5-dihydropyrazole derivatives

  摘要：

  A series of 3,5-diaryl-4,5-dihydropyrazole regioisomers, and their 1-acetylated derivatives, bearing a 3,4,5-trimethoxyphenyl moiety combined with a variety of substituted phenyl rings, was synthesized and evaluated for antitumor activity. Results of the in vitro assay against a non-small cell lung carcinoma cell line (NCI-H460) showed several compounds to be endowed with cytotoxicity in micromolar to sub-micromolar range, depending on substitution pattern and position of aryl rings on 4,5-dihydropyrazole core. Potent and selective activity was also observed in the NCI 60 human cancer cell line panel. 5-(3,4,5-Trimethoxyphenyl) pyrazolines 31 and 39 were found to possess potent antiproliferative activity against SR and MDA-MB-435, with GI(50) inhibitory values in nanomolar range. Structure-activity relationships revealed that introduction of a (hydroxy) acetyl group at N-1 of inactive 5-(3,4,5-trimethoxyphenyl) pyrazolines, results in a clear in vitro activating effect. Compound 31 (IC(50) = 5.16 mu M) showed inhibition of tubulin polymerization comparable to that of CA-4 (IC(50) = 4.92 mu M). (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.07.037