4-(5-phenyl-1(2)H-pyrazol-3-yl)-aniline | 82231-56-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(5-phenyl-1(2)H-pyrazol-3-yl)-aniline
• 英文别名: 4-(5-Phenyl-1(2)H-pyrazol-3-yl)-anilin；4-(5-phenyl-1H-pyrazol-3-yl)-aniline；4-(3-phenyl-1H-pyrazol-5-yl)aniline
• CAS: 82231-56-9
• 化学式: C₁₅H₁₃N₃
• 分子量: 235.288
• InChiKey: NALOEIBMYNAFPO-UHFFFAOYSA-N

物化性质

• 熔点：
  174 °C
• 沸点：
  488.7±30.0 °C(Predicted)
• 密度：
  1.213±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.7
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(5-phenyl-1(2)H-pyrazol-3-yl)-aniline 、 4-氯-3-三氟甲基异氰酸苯酯 在 三乙胺 作用下， 以 乙腈 为溶剂， 反应 12.0h， 以16%的产率得到N-(4-chloro-3-trifluoromethylphenyl)-N'-(4-(3-phenyl-1H-pyrazol-5-yl)-phenyl)-urea
  参考文献：
  名称：

  [EN] PYRAZOLE KINASE MODULATORS AND METHODS OF USE
  [FR] MODULATEURS DE KINASES A BASE DE PYRAZOLE ET LEURS PROCEDES D'UTILISATION

  摘要：

  公开号：

  WO2006033943A3
• 作为产物：
  描述：

  4'-aminochalcone 在 一水合肼 作用下， 以 乙醇 、 苯 为溶剂， 反应 11.0h， 生成 4-(5-phenyl-1(2)H-pyrazol-3-yl)-aniline
  参考文献：
  名称：

  Mahmoud; Soliman; Bakeer, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1990, vol. 29, # 9, p. 830 - 835

  摘要：

  DOI：

文献信息

• PhFl polystyrene: A new resin for solid phase organic synthesis
  作者：Konrad H. Bleicher、James R. Wareing

  DOI：10.1016/s0040-4039(98)00845-4

  日期：1998.6

  9-phenylfluoren-9-yl polystyrene based resin is described for the attachment of nitrogen and oxygen nucleophiles. Higher acid stability compared to standard trityl resins makes this solid support an interesting alternative in solid phase organic synthesis (SPOS). Several applications are shown and the results concerning yield and crude product purity are discussed below.

  描述了一种用于连接氮和氧亲核试剂的9-苯基芴基-9-基聚苯乙烯基树脂。与标准三苯甲基树脂相比，较高的酸稳定性使该固体载体成为固相有机合成（SPOS）中有趣的替代方法。显示了几种应用，下面讨论了有关收率和粗产物纯度的结果。
• Pyrazole Kinase Modulators And Methods Of Use
  申请人：Baik Tae-Gon

  公开号：US20070293507A1

  公开（公告）日：2007-12-20

  The present invention provides compounds for modulating protein kinase enzymatic activity for modulating cellular activities such as proliferation, differentiation, programmed cell death, migration and chemoinvasion. Compounds of the invention inhibit, regulate and/or modulate kinases. Methods of using the compounds and pharmaceutical compositions thereof to treat kinase-dependent diseases and conditions are also an aspect of the invention.

  本发明提供了用于调节蛋白激酶酶活性，以调节细胞活动（如增殖、分化、程序性细胞死亡、迁移和化学浸润）的化合物。本发明的化合物抑制、调节和/或调节激酶。使用这些化合物和制药组合物来治疗激酶依赖性疾病和状况也是本发明的一个方面。
• Discovery of 5-aryl-3-thiophen-2-yl-1H-pyrazoles as a new class of Hsp90 inhibitors in hepatocellular carcinoma
  作者：Samy Mohamady、Muhammad I. Ismail、Samar M. Mogheith、Yasmeen M. Attia、Scott D. Taylor

  DOI：10.1016/j.bioorg.2019.103433

  日期：2020.1

  Although hepatocellular carcinoma (HCC)-related mortality has increased over the past decades, treatment options are still very limited, underlining the need for developing new therapeutic strategies. The molecular chaperone heat shock protein 90 (Hsp90) plays a key role in post-translational maturation of many oncogenic client proteins that are important for survival and proliferation of cancer cells. Thus, inhibitors of Hsp90 are promising targets for many cancer types. In this study, 15 diarylpyrazole compounds were screened against MCF7 and HepG2 cell lines. Compound 8, which contained a thiophene group, demonstrated the highest antiproliferative activity against HepG2 cells having an IC50, of 0.083 mu M. Four additional diarylpyrazoles, each containing a thiophene group, were prepared and screened for antiproliferative activity. None of these four compounds exhibited superior activity to compound 8 on HepG2 cells. Therefore, compound 8 was selected for further in vitro assays. Cell cycle arrest was observed at the G2 phase in compound 8-treated cells. Compound 8 also caused a 7.7-fold increase in caspase-3. These results confirm the apoptotic effect of compound 8 on HepG2 cells. Moreover, compound 8 inhibited Hsp90 (IC50, = 2.67 +/- 0.18 mu M) in an in vitro assay and caused a 70.8% reduction in Hsp90 levels in a HepG2 cell-based assay. Additionally, compound 8 caused significant reduction in the levels of Hsp90 client proteins (Akt, c-Met, c-Raf, and EGFR) and a 1.57-fold increase in Hsp70. Molecular docking studies were also performed to predict the binding mode of compound 8 and followed by molecular dynamics simulations to give further insights into the binding mode of 8.
• Wieland, Chemische Berichte, 1904, vol. 37, p. 1146
  作者：Wieland

  DOI：——

  日期：——
• Copper on iron promoted one-pot synthesis of β-aminoenones and 3,5-disubstituted pyrazoles
  作者：Szabolcs Kovács、Zoltán Novák

  DOI：10.1016/j.tet.2013.08.047

  日期：2013.10

  The reaction of hydroximoyl chlorides with acetylenes in the presence of a copper on iron bimetallic system leads to beta-aminoenones via reductive ring opening of isoxazole intermediates. The valuable beta-aminoenone building blocks can be isolated or transformed into pyrazoles with the addition of hydrazine in a straightforward one-pot procedure. (C) 2013 Elsevier Ltd. All rights reserved.