1-acetyl-3-(4-methylphenyl)-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazole | 871307-77-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 1-acetyl-3-(4-methylphenyl)-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazole
• 英文别名: 1-(3-(p-tolyl)-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone；1-[5-(4-methylphenyl)-3-(3,4,5-trimethoxyphenyl)-3,4-dihydropyrazol-2-yl]ethanone
• CAS: 871307-77-6
• 化学式: C₂₁H₂₄N₂O₄
• 分子量: 368.433
• InChiKey: JGSSVHZGIZIRPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  60.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  溶剂黄146 、 1-(4-methylphenyl)-3-(3,4,5-trimethoxyphenyl)-prop-2-en-1-one 在 一水合肼 作用下， 反应 3.0h， 以71%的产率得到1-acetyl-3-(4-methylphenyl)-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

文献信息

• Synthesis and in vitro antitumor activity of new 4,5-dihydropyrazole derivatives
  作者：Cenzo Congiu、Valentina Onnis、Loredana Vesci、Massimo Castorina、Claudio Pisano

  DOI：10.1016/j.bmc.2010.07.037

  日期：2010.9

  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.