methyl 5-(3-methylphenyl)-1-phenylpyrazole-3-carboxylate | 235789-33-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 5-(3-methylphenyl)-1-phenylpyrazole-3-carboxylate
• CAS: 235789-33-0
• 化学式: C₁₈H₁₆N₂O₂
• 分子量: 292.337
• InChiKey: DKVQUQUZLOOVLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  44.1
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  methyl 5-(3-methylphenyl)-1-phenylpyrazole-3-carboxylate 在 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 10.0h， 生成 (1-phenyl-5-(m-tolyl)-1H-pyrazol-3-yl)methyl 2-((5-hydroxy-4-oxo-2-phenyl-4H-chromen-7-yl)oxy)acetate
  参考文献：
  名称：

  Design and biological evaluation of novel hybrids of 1, 5-diarylpyrazole and Chrysin for selective COX-2 inhibition

  摘要：

  The overexpress of COX-2 was clearly associated with carcinogenesis and COX-2 as a possible target has long been exploited for cancer therapy. In this work, we described the design and synthesis of a series of diarylpyrazole derivatives integrating with chrysin. Among them, compound e9 exhibited the most potent inhibitory activity against COX-2 and antiproliferative activity against Hela cells with IC50 value of 1.12 mu M. Further investigation revealed that e9 could induce apoptosis of Hela cells by mitochondrial depolarization and block the G1 phase of cell cycle in a dose-dependent manner. Besides, molecular docking simulation results was further confirmed that e9 could bind well with COX-2. In summary, compound e9 may be promising candidates for cancer therapy.

  DOI：

  10.1016/j.bmc.2018.07.022
• 作为产物：
  描述：

  3'-甲基苯乙酮 在 盐酸 、 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 反应 11.0h， 生成 methyl 5-(3-methylphenyl)-1-phenylpyrazole-3-carboxylate
  参考文献：
  名称：

  1,5-二芳基取代吡唑塞克硝唑酯衍生物的设计、合成和抗肿瘤活性评价

  摘要：

  根据药物杂交原理，通过多种1,5-二芳基吡唑-3-羧酸与塞克硝唑的组合，合成了一系列新型1,5-二芳基取代吡唑塞克硝唑酯衍生物（6aa - 6gc）。对肿瘤和正常细胞系的体外抗肿瘤/细胞毒活性，包括 NCI-H460（肺肿瘤细胞）、MCG-803（胃肿瘤细胞）、Skov-3（卵巢肿瘤细胞）、BEL-7404（肝肿瘤细胞）和 HL-7702（正常肝细胞），已使用 MTT 测定进行评估。所有化合物都显示出对四种肿瘤细胞系的有希望的抑制活性。该IC 50的6BC靠在BEL-7404细胞为2.03μM，而那些的6FC针对 NCI-H460，MCG-803 和 Skov-3 分别为 1.34、0.14 和 0.87 μM。所有这些值都远低于顺铂的值。此外，6fc和6bc也被证实对正常人肝细胞相当安全，因为其 IC 50值低于顺铂。基于这些结果，进一步对6fc和6bc进行细胞周期分析、细胞凋亡率检测和

  DOI：

  10.1002/jhet.4302

文献信息

• Synthesis and Herbicidal Activity of 1,5-Diarylpyrazole Derivatives.
  作者：Noriaki KUDO、Satoru FURUTA、Misa TANIGUCHI、Takeshi ENDO、Kazuo SATO

  DOI：10.1248/cpb.47.857

  日期：——

  A series of diarylpyrazolecarboxylates and carboxamides were prepared, and their herbicidal activities were investigated. Some of these compounds showed noticeable pre-emergent herbicidal activities against various kinds of weeds. Among the synthesized compounds, methyl 4-chloro-1-(2, 5-difluorophenyl)-5-(4-flurophenyl)-pyzazole-3-carboxylate 19t exhibited good activity. Diarylimidazolecarboxylates and carboxamides were also synthesized, but they did not show any herbicidal activities.

  制备了一系列二芳基吡唑羧酸盐和羧酰胺，并研究了它们的除草活性。其中一些化合物对各种杂草具有明显的萌前除草活性。在合成的化合物中，4-氯-1-(2, 5-二氟苯基)-5-(4-氟苯基)-哒唑-3-羧酸甲酯 19t 表现出良好的活性。还合成了二咪唑羧酸盐和羧酰胺，但它们没有显示出任何除草活性。
• US8673911B2
  申请人：——

  公开号：US8673911B2

  公开（公告）日：2014-03-18
• Design and biological evaluation of novel hybrids of 1, 5-diarylpyrazole and Chrysin for selective COX-2 inhibition
  作者：Shen-Zhen Ren、Zhong-Chang Wang、Xiao-Hua Zhu、Dan Zhu、Zhang Li、Fa-Qian Shen、Yong-Tao Duan、Han Cao、Jing Zhao、Hai-Liang Zhu

  DOI：10.1016/j.bmc.2018.07.022

  日期：2018.8

  The overexpress of COX-2 was clearly associated with carcinogenesis and COX-2 as a possible target has long been exploited for cancer therapy. In this work, we described the design and synthesis of a series of diarylpyrazole derivatives integrating with chrysin. Among them, compound e9 exhibited the most potent inhibitory activity against COX-2 and antiproliferative activity against Hela cells with IC50 value of 1.12 mu M. Further investigation revealed that e9 could induce apoptosis of Hela cells by mitochondrial depolarization and block the G1 phase of cell cycle in a dose-dependent manner. Besides, molecular docking simulation results was further confirmed that e9 could bind well with COX-2. In summary, compound e9 may be promising candidates for cancer therapy.
• Design, syntheses and antitumor activities evaluation of 1,5‐diaryl substituted pyrazole secnidazole ester derivatives
  作者：Qing‐Hu Teng、Gui‐Xia Sun、Shu‐Ying Luo、Kai Wang、Fu‐Pei Liang

  DOI：10.1002/jhet.4302

  日期：2021.8

  According to the drug hybridization principle, a series of novel 1,5-diaryl substituted pyrazole secnidazole ester derivatives (6aa–6gc) have been synthesized by the combinations of various 1,5-diarylpyrazole-3-carboxylic acids with secnidazole. The in vitro antitumor/cytotoxicities activities against tumor and normal cell lines, including NCI-H460 (lung tumor cell), MCG-803 (gastric tumor cell), Skov-3

  根据药物杂交原理，通过多种1,5-二芳基吡唑-3-羧酸与塞克硝唑的组合，合成了一系列新型1,5-二芳基取代吡唑塞克硝唑酯衍生物（6aa - 6gc）。对肿瘤和正常细胞系的体外抗肿瘤/细胞毒活性，包括 NCI-H460（肺肿瘤细胞）、MCG-803（胃肿瘤细胞）、Skov-3（卵巢肿瘤细胞）、BEL-7404（肝肿瘤细胞）和 HL-7702（正常肝细胞），已使用 MTT 测定进行评估。所有化合物都显示出对四种肿瘤细胞系的有希望的抑制活性。该IC 50的6BC靠在BEL-7404细胞为2.03μM，而那些的6FC针对 NCI-H460，MCG-803 和 Skov-3 分别为 1.34、0.14 和 0.87 μM。所有这些值都远低于顺铂的值。此外，6fc和6bc也被证实对正常人肝细胞相当安全，因为其 IC 50值低于顺铂。基于这些结果，进一步对6fc和6bc进行细胞周期分析、细胞凋亡率检测和