1-acetyl-5-(benzo[d][1,3]dioxol-5-yl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole | 1376396-11-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 1-acetyl-5-(benzo[d][1,3]dioxol-5-yl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole
• 英文别名: 1-[3-(1,3-Benzodioxol-5-yl)-5-(4-fluorophenyl)-3,4-dihydropyrazol-2-yl]ethanone；1-[3-(1,3-benzodioxol-5-yl)-5-(4-fluorophenyl)-3,4-dihydropyrazol-2-yl]ethanone
• CAS: 1376396-11-0
• 化学式: C₁₈H₁₅FN₂O₃
• 分子量: 326.327
• InChiKey: ABGQICRXAWVMLP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  51.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  胡椒醛 在 一水合肼 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 1-acetyl-5-(benzo[d][1,3]dioxol-5-yl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole
  参考文献：
  名称：

  1-取代的3-芳基-5-芳基(杂芳基)-2-吡唑啉的合成及其抗肿瘤活性研究

  摘要：

  合成了三个系列的新型 1,3,5-三取代 2-吡唑啉衍生物，其中含有噻吩和苯并二氧杂环戊烷作为潜在的抗肿瘤剂。获得的化合物的体外抗肿瘤活性在美国国家癌症研究所 (NCI) 进行了测定。5-(benzo[d][1,3]dioxol-5-yl)-3-(4-甲氧基苯基)-4,5-dihydro-1H-pyrazole-1-carbothioamide (9a) 是最突出的由于其对白血病 (RPMI-8226)、肾癌 (UO-31) 和前列腺癌 (DU-145) 细胞系具有显着的活性，GI50 值分别为 1.88、1.91 和 1.94 µM。

  DOI：

  10.1002/ardp.201100170

文献信息

• Synthesis of 1-Substituted 3-Aryl-5-aryl(hetaryl)-2-pyrazolines and Study of Their Antitumor Activity
  作者：Braulio Insuasty、Leidy Chamizo、Jhon Muñoz、Alexis Tigreros、Jairo Quiroga、Rodrigo Abonía、Manuel Nogueras、Justo Cobo

  DOI：10.1002/ardp.201100170

  日期：2012.4

  Three series of novel 1,3,5‐trisubstituted 2‐pyrazoline derivatives containing thiophene and benzodioxol moieties as potential antitumor agents were synthesized. The in vitro antitumor activity of the obtained compounds was determined at the National Cancer Institute (NCI). The 5‐(benzo[d][1,3]dioxol‐5‐yl)‐3‐(4‐methoxyphenyl)‐4,5‐dihydro‐1H‐pyrazole‐1‐carbothioamide (9a) is the most prominent of the

  合成了三个系列的新型 1,3,5-三取代 2-吡唑啉衍生物，其中含有噻吩和苯并二氧杂环戊烷作为潜在的抗肿瘤剂。获得的化合物的体外抗肿瘤活性在美国国家癌症研究所 (NCI) 进行了测定。5-(benzo[d][1,3]dioxol-5-yl)-3-(4-甲氧基苯基)-4,5-dihydro-1H-pyrazole-1-carbothioamide (9a) 是最突出的由于其对白血病 (RPMI-8226)、肾癌 (UO-31) 和前列腺癌 (DU-145) 细胞系具有显着的活性，GI50 值分别为 1.88、1.91 和 1.94 µM。
• Synthesis, biological evaluation, 3D-QSAR studies of novel aryl-2H-pyrazole derivatives as telomerase inhibitors
  作者：Yin Luo、Shuai Zhang、Ke-Ming Qiu、Zhi-Jun Liu、Yu-Shun Yang、Jie Fu、Wei-Qing Zhong、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2012.12.010

  日期：2013.2

  A series of novel aryl-2H-pyrazole derivatives bearing 1,4-benzodioxan or 1,3-benzodioxole moiety were designed as potential telomerase inhibitors to enhance the ability of aryl-2H-pyrazole derivatives to inhibit telomerase, a target of anticancer. The telomerase inhibition tests showed that compound 16A displayed the most potent inhibitory activity with IC50 value of 0.9 mu M for telomerase. The antiproliferative tests showed that compound 16A exhibited high activity against human gastric cancer cell SGC-7901 and human melanoma cell B16-F10 with IC50 values of 18.07 and 5.34 mu M, respectively. Docking simulation showed that compound 16A could bind well with the telomerase active site and act as telomerase inhibitor. 3D-QSAR model was also built to provide more pharmacophore understanding that could be used to design new agents with more potent telomerase inhibitory activity. (C) 2012 Elsevier Ltd. All rights reserved.