3-(1-苯基-3-对甲苯-1H-吡唑-4-基)-丙烯酸 | 108446-74-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 3-(1-苯基-3-对甲苯-1H-吡唑-4-基)-丙烯酸
• 英文名称: 3-[3-(4-methylphenyl)-1-phenyl-1H-pyrazol-4-yl]prop-2-enoic acid
• 英文别名: 3-[3-(4-methylphenyl)-1-phenylpyrazol-4-yl]prop-2-enoic acid
• CAS: 108446-74-8
• 化学式: C₁₉H₁₆N₂O₂
• 分子量: 304.348
• InChiKey: VKOYKKRRVGLIMR-UHFFFAOYSA-N

物化性质

• 熔点：
  220-221 °C(Solv: ethanol (64-17-5))
• 沸点：
  523.7±38.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  55.1
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 海关编码：
  2933199090

反应信息

• 作为反应物：
  描述：

  3-(1-苯基-3-对甲苯-1H-吡唑-4-基)-丙烯酸 在 Renay nickel sodium hydroxide 、 氯化亚砜 、 一水合肼 、 三乙胺 作用下， 以 乙醇 、 乙腈 、 苯 为溶剂， 反应 3.0h， 生成 3-[3-(4-methylphenyl)-1-phenylpyrazol-4-yl]-N-naphthalen-1-ylpropanamide
  参考文献：
  名称：

  摘要：

  3-Aryl(heteryl)-4-formylpyrazoles by condensation with malonic acid furnish 3-[3-aryl(heteryl)pyrazol-4-yl]propenoic acids that in the presence of Raney nickel are reduced by hydrazine hydrate to 3-[3-aryl(heteryl)pyrazol-4-yl]propanoic acids. The successive conversion of both type acids into the corresponding acyl chlorides, esters, and amides was performed.

  DOI：

  10.1023/a:1020905727368
• 作为产物：
  描述：

  2-((1-苯基-3-(对甲苯基)-1H-吡唑-4-基)亚甲基)丙二酸 以 吡啶 为溶剂， 反应 0.5h， 生成 3-(1-苯基-3-对甲苯-1H-吡唑-4-基)-丙烯酸
  参考文献：
  名称：

  Bernard; Hulley; Molenda, Pharmazie, 1986, vol. 41, # 8, p. 560 - 562

  摘要：

  DOI：

文献信息

• Unveiling novel diphenyl-1H-pyrazole based acrylates tethered to 1,2,3-triazole as promising apoptosis inducing cytotoxic and anti-inflammatory agents
  作者：Mohemmed Faraz Khan、Tarique Anwer、Afroz Bakht、Garima Verma、Wasim Akhtar、M. Mumtaz Alam、Moshahid Alam Rizvi、Mymoona Akhter、Mohammad Shaquiquzzaman

  DOI：10.1016/j.bioorg.2019.03.071

  日期：2019.6

  the apoptosis inducing potential of the compounds was determined by Hoechst staining and DNA fragmentation assay. Colony formation inhibition assay was also carried out to determine the long term cytotoxic potential of the molecules. Moreover, compounds 6e, 6f and 6n were also evaluated for anti-inflammatory activity by protein albumin denaturation assay and red blood cell membrane stabilizing assay

  微弱和次佳的治疗反应以及与现有抗癌治疗相关的副作用，已需要开发新的治疗方法来遏制该疾病。考虑到当前情况，按照多步反应方案合成了一系列1,2,3-三唑连接的3-（1,3-二苯基-1H-吡唑-4-基）丙烯酸酯。通过针对四类人癌细胞系MCF-7（乳腺），A549（肺）和HCT-116和HT-29（结肠）的体外磺基若丹明B试验，初步筛选抗癌潜能。经评估，几种化合物对所有细胞系均显示出有希望的生长抑制作用，特别是化合物6e，6f和6n。其中，化合物6f对A549，HCT-116，MCF-7和HT-29细胞系的IC50值分别为1.962、3.597、1.764和4.496 µM。此外，通过Hoechst染色和DNA片段化分析确定化合物的凋亡诱导潜力。还进行了菌落形成抑制试验以确定该分子的长期细胞毒性潜力。此外，还通过蛋白白蛋白变性测定法和红细胞膜稳定测定法评价了化合物6e，6f和6n的抗炎活性。
• Synthesis, biological evaluation and molecular docking studies of 3-(1,3-diphenyl-1H-pyrazol-4-yl)-N-phenylacrylamide derivatives as inhibitors of HDAC activity
  作者：Xi Li、Jia-Lin Liu、Xian-Hui Yang、Xiang Lu、Ting-Ting Zhao、Hai-Bin Gong、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2012.05.031

  日期：2012.7

  In present study, a series of 3-(1,3-diphenyl-1H-pyrazol-4-yl)-N-phenylacrylamide derivatives (5a-8d) were designed, synthesized, and evaluated for HDAC inhibition and tumor cell antiproliferation. All of these compounds are reported for the first time, the chemical structures of these compounds were confirmed by means of H-1 NMR, ESI-MS and elemental analyzes. Among the compounds, compound 8c showed the most potent biological activity against HCT116 cancer cell line (IC50 of 0.42 +/- 0.02 mu M for HDAC-1 and IC50 = 0.62 +/- 0.02 for HCT116). Docking simulation was performed to position compound 8c into the HDAC active site to determine the probable binding model. The results of antiproliferative assay and western-blot demonstrated that compound 8c with potent inhibitory activity in tumor growth inhibition may be a potential anticancer agent against HCT116 cancer cell. (C) 2012 Elsevier Ltd. All rights reserved.
• Microwave‐Assisted Synthesis of 3‐(4‐Pyrazolyl)propenoic Acids
  作者：Vitaliy O. Chornous、Mykhaylo K. Bratenko、Mykhaylo V. Vovk

  DOI：10.1081/scc-120027241

  日期：2004.12.31

  Under microwave activation, pyrazole-4-carboxaldehydes react with malonic acid in the presence of a small amount of pyridine to give 3-(4-pyrazolyl)propenoic acids in high yields.
• 4-Functionally-substituted 3-heterylpyrazoles: XVI. 3-(3-Arylpyrazol-4-yl)propyonic acids
  作者：M. K. Bratenko、V. A. Chornous、M. V. Vovk

  DOI：10.1134/s1070428006050095

  日期：2006.5

  Bromination of 3-(3-arylpyrazol-4-yl)acrylic acids led to the formation of 2-bromo-3-(3-arylpyrazol-4yl)acrylic acids that were converted into 3-(3-arylpyrazol-4-yl)propynoic acids by treatment of potassium hydroxide with an alcoholic solution.
• Bernard; Hulley; Molenda, Pharmazie, 1986, vol. 41, # 8, p. 560 - 562
  作者：Bernard、Hulley、Molenda、Stochla、Wrzeciono

  DOI：——

  日期：——