5-(2-nitrophenyl)-3-phenyl-1H-pyrazole | 178114-26-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-(2-nitrophenyl)-3-phenyl-1H-pyrazole
• CAS: 178114-26-6
• 化学式: C₁₅H₁₁N₃O₂
• 分子量: 265.271
• InChiKey: HYVKIASURAIQJE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.65
• 重原子数：
  20.0
• 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：
  71.82
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-(2-nitrophenyl)-3-phenyl-1H-pyrazole 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 25.0 ℃ 、206.84 kPa 条件下， 反应 8.5h， 生成 2-Phenyl-6H-pyrazolo[1,5-c]quinazolin-5-one
  参考文献：
  名称：

  Colotta; Catarzi; Varano, Il Farmaco, 1996, vol. 51, # 4, p. 223 - 229

  摘要：

  DOI：
• 作为产物：
  描述：

  4,5-dihydro-5-(2-nitrophenyl)-3-phenyl-1H-pyrazole 在 碘 、 二甲基亚砜 作用下， 反应 4.0h， 以92%的产率得到5-(2-nitrophenyl)-3-phenyl-1H-pyrazole
  参考文献：
  名称：

  二氢吡唑并[1,5-c]喹唑啉通过抑制拓扑异构酶II对大鼠C6神经胶质瘤细胞的抗癌活性

  摘要：

  报道了作为人类拓扑异构酶 II (TopoII) 催化抑制剂的二氢吡唑并 [1,5-c] 喹唑啉 (1a-h) 的设计和合成。研究了这些化合物对 C6 大鼠神经胶质细胞系的抗增殖活性。发现两种化合物 1b 和 1h 是针对神经胶质瘤细胞的有效细胞毒性剂，并发挥选择性 TopoII 抑制活性。此外，通过 DCFDA 测定法测量，这些化合物诱导活性氧水平的改变，并且发现在较低浓度下诱导细胞周期停滞在 G1 期，在较高浓度下诱导细胞凋亡。分子模型进一步证实了选定的研究分子与 TopoII 的相互作用。

  DOI：

  10.1002/ardp.201800023

文献信息

• Synthesis of 3,5-Disubstituted-1H-Pyrazoles from Acid Chlorides, Alkynes, and Hydrazine in the Presence of Silica-Supported-Zinc Bromide
  作者：Ali Keivanloo、Mohammad Bakherad、Shahrzad Samangooei

  DOI：10.3184/174751915x14382642961716

  日期：2015.8

  An efficient one-pot palladium- and copper-free procedure has been developed for a convenient synthesis of 3,5 -disubstituted-1H-pyrazoles from various acid chlorides, terminal alkynes and hydrazine by a coupling reaction and cyclocondensation sequence. Acid chlorides react with terminal alkynes in the presence of silica-supported-zinc bromide to give α,β-unsaturated ynones, and in situ conversion

  已开发出一种高效的一锅式无钯和无铜工艺，可通过偶联反应和环缩合顺序从各种酰氯、末端炔烃和肼方便地合成 3,5-二取代-1H-吡唑。在二氧化硅负载的溴化锌存在下，酰氯与末端炔烃反应生成 α,β-不饱和炔酮，并通过肼环缩合反应原位转化为吡唑。
• Synthesis and xanthine oxidase inhibitory activity of 5,6-dihydropyrazolo/pyrazolo[1,5-c]quinazoline derivatives
  作者：Deependra Kumar、Gagandeep Kaur、Arvind Negi、Sanjeev Kumar、Sandeep Singh、Raj Kumar

  DOI：10.1016/j.bioorg.2014.08.007

  日期：2014.12

  Some 5,6-dihydropyrazolo/pyrazolo[1,5-c]quinazoline derivatives were rationally designed, synthesized and evaluated for in vitro xanthine oxidase inhibitory activity for the first time. Some notions about structure activity relationships are presented. The compounds 6g, 6h and 6e were found to be significantly active against XO. The compound 6g emerged as the most potent XO inhibitor as compared to

  首次合理设计，合成和评价了一些5,6-二氢吡唑并/吡唑并[1,5- c ]喹唑啉衍生物的体外黄嘌呤氧化酶抑制活性。提出了有关结构活动关系的一些概念。发现化合物6g，6h和6e对XO具有显着活性。与别嘌呤醇和自由基清除剂相比，化合物6g成为最有效的XO抑制剂。6g的分子对接 进入XO活性位点突出了它的结合方式和重要的相互作用，例如氢键，与氨基酸残基如Ser876，Thr1010，Phen914，Phe1009和Phe649的π-π堆积，以及与二氧硫钼钼（MOS）的紧邻。
• N₂H₄–H₂O Enabled Umpolung Cyclization of <i>o</i>-Nitro Chalcones for the Construction of Quinoline <i>N</i>-Oxides
  作者：Guan Zhang、Kai Yang、Shihui Wang、Qiang Feng、Qiuling Song

  DOI：10.1021/acs.orglett.0c04162

  日期：2021.1.15
• E-pharmacophore guided discovery of pyrazolo[1,5-c]quinazolines as dual inhibitors of topoisomerase-I and histone deacetylase
  作者：Gaurav Joshi、Sourav Kalra、Umesh Prasad Yadav、Praveen Sharma、Pankaj Kumar Singh、Suyog Amrutkar、Arshad J. Ansari、Santosh Kumar、Ashoke Sharon、Sadhana Sharma、Devesh M. Sawant、Uttam C. Banerjee、Sandeep Singh、Raj Kumar

  DOI：10.1016/j.bioorg.2019.103409

  日期：2020.1

  In the quest to ameliorate the camptothecin (CPT) downsides, we expedite to search for stable non-CPT analogues among 11 motifs of pyrazoloquinazolines reported. E-pharmacophore drug design approach helped filtering out pyrazolo [1,5-c] quinazolines as Topoisomerase I (Topol) 'interfacial' inhibitors. Three compounds, 3c, 3e, and 31 were shown to be potent non-intercalating inhibitors of Topol specifically and showed cancer cell-specific cytotoxicity in lung, breast and colon cancer cell lines. The compounds induced cell cycle arrest at S-phase, mitochondrial cell death pathway and modulated oxidative stress in cancer cells. Furthermore, a preliminary study was conducted to explore the feasibility of these compounds to be developed as dual TopoI-HDAC1 (histone deacetylase 1) inhibitors (4a) to combat resistance. Compound 4a was found to possess dual inhibitory capabilities in-vitro. Cytotoxic potential of 4a was found to be significantly higher than parent compound in 2D as well as 3D cancer cell models. Probable binding modes of 4a with Topol and HDAC1 active sites were examined by molecular modelling.