1-acetyl-3-(4-aminophenyl)-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazole | 1252008-28-8

• 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-aminophenyl)-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazole
• 英文别名: 1-[5-(4-Aminophenyl)-3-(3,4,5-trimethoxyphenyl)-3,4-dihydropyrazol-2-yl]ethanone
• CAS: 1252008-28-8
• 化学式: C₂₀H₂₃N₃O₄
• 分子量: 369.42
• InChiKey: UXONERPOABEBOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  86.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-acetyl-3-(4-aminophenyl)-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazole 、 对乙酰胺基苯磺酰氯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以81%的产率得到4-acetamido-N-(4-(1-acetyl-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazol-3-yl)phenyl)benzsulphonamide
  参考文献：
  名称：

  Amir, Mohd; Ali, Sazid; Somakala, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2016, vol. 55B, # 4, p. 478 - 485

  摘要：

  DOI：
• 作为产物：
  描述：

  1-acetyl-3-[4-[(tert-buthoxycarbonyl)amino]phenyl]-5-(3,4,5-trimethoxyphenyl)-4,5-dihydro-1H-pyrazole 在 三氟乙酸 、 氨 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 16.0h， 以76%的产率得到1-acetyl-3-(4-aminophenyl)-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.
• Amir, Mohd; Ali, Sazid; Somakala, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2016, vol. 55B, # 4, p. 478 - 485
  作者：Amir, Mohd、Ali, Sazid、Somakala

  DOI：——

  日期：——