3-(4-Chloro-phenyl)-1-phenyl-1H-pyrazole-4-carbonyl chloride | 373627-28-2

• 英文名称: 3-(4-Chloro-phenyl)-1-phenyl-1H-pyrazole-4-carbonyl chloride
• 英文别名: 3-(4-chlorophenyl)-1-phenylpyrazole-4-carbonyl chloride
• CAS: 373627-28-2
• 化学式: C₁₆H₁₀Cl₂N₂O
• 分子量: 317.174
• InChiKey: VNLREBOKFURCDF-UHFFFAOYSA-N

物化性质

• 沸点：
  477.3±35.0 °C(Predicted)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.57
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  34.89
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  3-(4-Chloro-phenyl)-1-phenyl-1H-pyrazole-4-carbonyl chloride 在 ammonium hydroxide 、 叠氮基三甲基硅烷 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 1.0h， 生成 N-[1-phenyl-3-(4-chlorophenyl)]-4-pyrazolylurea
  参考文献：
  名称：

  摘要：

  DOI：

  10.1023/a:1013982203774
• 作为产物：
  描述：

  苯肼,盐酸盐 在 potassium permanganate 、 氯化亚砜 、 sodium acetate 、 三氯氧磷 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 14.0h， 生成 3-(4-Chloro-phenyl)-1-phenyl-1H-pyrazole-4-carbonyl chloride
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular docking studies of pyrazole derivatives coupling with a thiourea moiety as novel CDKs inhibitors

  摘要：

  It was discovered that a number of cyclin dependent kinase inhibitors containing the pyrazole core structure exhibited high inhibitory potency against broad-range CDKs and corresponding anti-proliferative activities. This information guided us to design and synthesize a series of 1,3-diphenyl-N-(phenylcarbamothioyl)-1H-pyrazole-4-carboxamide derivatives (5a-10d), and evaluate their biological activities as CDKs inhibitors. Among all the synthesized compounds, compound 10b inhibited CDK2 with an IC50 value of 25 nM, counteracting tumor cell proliferation of three cancer cell lines (H460, MCF-7, A549) in the micromolar range (from 0.75 mu M to 4.21 mu M), In addition, flow cytometry indicated that compound 10b could induce cycle G(0)/G(1) phase arrest in A549 cells with a dose dependent. Taken together, compound 10b could be selected for further preclinical evaluation. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.07.003

文献信息

• Discovery of N-(benzyloxy)-1,3-diphenyl-1H-pyrazole-4-carboxamide derivatives as potential antiproliferative agents by inhibiting MEK
  作者：Xian-Hai Lv、Zi-Li Ren、Ben-Guo Zhou、Qing-Shan Li、Ming-Jie Chu、Dao-Hong Liu、Kai Mo、Li-Song Zhang、Xiao-Kang Yao、Hai-Qun Cao

  DOI：10.1016/j.bmc.2016.08.002

  日期：2016.10

  inhibitor has been demonstrated significant clinical benefit for blocking MAPK pathway activation and possibly could block reactivation of the MAPK pathway at the time of BRAF inhibitor resistance. Twenty N-(benzyloxy)-1,3-diphenyl-1H-pyrazole-4-carboxamide derivatives have been designed and synthesized as MEK inhibitors, and their biological activities were evaluated. Among these compounds, compound 7b

  丝裂原活化蛋白激酶（MAPK）信号转导途径已被证明在肿瘤发生和癌症发展中起重要作用。已经证明MEK抑制剂对于阻断MAPK途径活化具有显着的临床益处，并且可能在BRAF抑制剂抵抗时阻断MAPK途径的再活化。设计并合成了二十种N-（苄氧基）-1,3-二苯基-1H-吡唑-4-羧酰胺衍生物作为MEK抑制剂，并对其生物学活性进行了评估。在这些化合物中，化合物7b表现出最强的抑制活性，对MEK1的IC50为91nM，对A549细胞的GI50为0.26μM。进行了SAR分析和对接模拟，以提供可用于进一步结构优化的关键药效​​团线索。
• ——
  作者：V. A. Chornous、N. V. Mel'nichenko、M. K. Bratenko、M. V. Vovk

  DOI：10.1023/a:1016394311649

  日期：——

  3-Aryl(heteryl)-1-phenyl-4-pyrazolecarbonyl isothiocyanates were synthesized by treatment of 3-aryl(heteryl)-1-phenyl-4-pyrazolecarbonyl chlorides with lead, sodium, or ammonium thiocyanate. Their reactions with amines, hydrazines, and acylhydrazines gave the corresponding thioureas and thiosemicarbazides.
• ——
  作者：M.K. Bratenko、V.A. Chornous、M.V. Vovk

  DOI：10.1023/a:1012490120976

  日期：——

  3-Aryl(heteryl)-4-formylpyrazoles were cleanly oxidized by potassium permanganate in water-pyridine medium to afford in high yield 3-aryl(heteryl)pyrazole-4-carboxylic acids, that were further converted into the corresponding chlorides and amides.
• ——
  作者：V. A. Chornous、M. K. Bratenko、M. V. Vovk、I. I. Sidorchuk

  DOI：10.1023/a:1010432029236

  日期：——
• The first-in-class pyrazole-based dual InhA-VEGFR inhibitors towards integrated antitubercular host-directed therapy
  作者：Marwa M. Shaaban、Mohamed Teleb、Hanan M. Ragab、Monica Singh、Bassma H. Elwakil、Lamia A. Heikal、D. Sriram、Mona A. Mahran

  DOI：10.1016/j.bioorg.2024.107179

  日期：2024.4