3-(4-methoxyphenyl)-5-(4-nitrophenyl)-1H-pyrazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4-methoxyphenyl)-5-(4-nitrophenyl)-1H-pyrazole
• 化学式: C₁₆H₁₃N₃O₃
• 分子量: 295.298
• InChiKey: HZGKYBLBZDROKF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  83.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-methoxyphenyl)-5-(4-nitrophenyl)-1H-pyrazole 在 1% Pd/C 、 氢气 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 4-(3-(4-methoxyphenyl)-1H-pyrazol-5-yl)aniline
  参考文献：
  名称：

  3,5-Diaryl-1H-pyrazole as a molecular scaffold for the synthesis of apoptosis-inducing agents

  摘要：

  The scaffold of 3,5-diaryl-1H-pyrazole was selected as a molecular template to synthesize novel growth-inhibitory agents in the present study. Our findings suggested that analogs bearing electron-withdrawing groups on one ring while electron-donating groups on another reveal significant activities. In particular, 26 bearing a 1,1'-biphenyl moiety displayed the most potent activity against OVCA, SW620, H460 and AGS cells with GI(50) values of 0.67, 0.89, 0.73 and 0.79 mu M, respectively. The mechanistic study revealed that 26-mediated apoptosis-inducing effect on OVCA cells was, in part, attributed to the inhibition of protein kinase B/Akt activity, accompanied by the mitochondrial apoptotic pathway through the activation of caspase-9, caspase-3, as well as the cleavage of protein poly(ADP-ribose) polymerase ( PARP) and DNA fragmentation. Further structure-activity relationship study employed by Comparative Molecular Field Analysis (CoMFA) was carried out with q(2) and R(2) values of 0.671 and 0.846, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.03.016
• 作为产物：
  描述：

  4'-methoxy-4-nitrochalcone 在 sodium persulfate 、 一水合肼 作用下， 反应 1.83h， 生成 3-(4-methoxyphenyl)-5-(4-nitrophenyl)-1H-pyrazole
  参考文献：
  名称：

  One-Pot Synthesis of 3,5-Diphenyl-1H-pyrazoles from Chalcones and Hydrazine under Mechanochemical Ball Milling

  摘要：

  A highly efficient and environmentally friendly method has been developed for facile synthesis of 3,5-diphenyl-1H-pyrazoles under mechanochemical ball-milling conditions. The advantages of short reaction time, high efficiency, no separation of in situ generated intermediate, using cheap sodium persulfate as the oxidant, together with very simple work-up procedure, make this one-pot and solvent-free protocol a green and powerful alternative to traditional methods for the synthesis of these kinds of compounds.

  DOI：

  10.3987/com-13-12867

文献信息

• 1,3-Diketones from Acid Chlorides and Ketones:  A Rapid and General One-Pot Synthesis of Pyrazoles
  作者：Stephen T. Heller、Swaminathan R. Natarajan

  DOI：10.1021/ol060570p

  日期：2006.6.1

  [reaction: see text] 1,3-Diketones were synthesized directly from ketones and acid chlorides and were then converted in situ into pyrazoles by the addition of hydrazine. This method is extremely fast, general, and chemoselective, allowing for the synthesis of previously inaccessible pyrazoles and synthetically demanding pyrazole-containing fused rings.

  [反应：见正文] 1,3-二酮直接由酮和酰氯合成，然后通过加入肼原位转化为吡唑。该方法非常快速，通用且具有化学选择性，可以合成以前无法获得的吡唑和需要合成的含吡唑的稠环。
• Stereoselective Direct <i>N</i> ‐Trifluoropropenylation of Heterocycles with a Hypervalent Iodonium Reagent
  作者：János T. Csenki、Ádám Mészáros、Zsombor Gonda、Zoltán Novák

  DOI：10.1002/chem.202102840

  日期：2021.11.11

  E-selective trifluoropropenylation of versatile N-heterocycles was developed with the utilization of trifluoropropenyliodonium salts. The procedure enables the straightforward direct introduction of the trifluoroalkenyl moiety into heterocyclic scaffolds under simple and mild reaction conditions.

  利用三氟丙烯基碘鎓盐开发了多功能 N-杂环的E-选择性三氟丙烯基化。该程序能够在简单和温和的反应条件下直接将三氟烯基部分直接引入杂环支架中。
• A highly efficient heterogeneous palladium-catalyzed cascade three-component reaction of acid chlorides, terminal alkynes and hydrazines leading to pyrazoles
  作者：Qiurong Chen、Fang Yao、Lin Yin、Mingzhong Cai

  DOI：10.1016/j.jorganchem.2015.12.037

  日期：2016.2

  MCM-41-immobilized palladium(II) complex [MCM-41-2N–Pd(OAc)2] and 1.0 mol% of CuI, acid chlorides were coupled with terminal alkynes in Et3N at 50 °C to give α,β-unsaturated ynones, which were converted in situ into pyrazoles by the cycloaddition of hydrazines at room temperature with acetonitrile as cosolvent. The cascade reactions generated a variety of pyrazole derivatives in moderate to good yields, and

  在0.5摩尔％的3-（2-氨基乙基氨基）丙基官能化的MCM-41固定的钯（II）配合物[MCM-41-2N-Pd（OAc）2 ]和1.0摩尔％的CuI的存在下，酰氯将其与末端炔烃在50°C的Et 3 N中偶合，得到α，β-不饱和炔酮，通过在室温下以乙腈为助溶剂将肼环加成，将其原位转化为吡唑。级联反应以中等至良好的产率生成了多种吡唑衍生物，并且这种非均相钯催化剂显示出比PdCl 2（PPh 3）2更高的催化活性，并且可以被回收并重复使用至少10次连续试验而活性没有降低。
• DABCO-promoted synthesis of pyrazoles from tosylhydrazones and nitroalkenes
  作者：Meng Tang、Wen Zhang、Yuanfang Kong

  DOI：10.1039/c3ob41435c

  日期：——

  An efficient synthesis of pyrazoles from tosylhydrazones and nitroalkenes was developed. In comparison with the previously reported 1,3-dipolar cycloaddition reaction of diazo compounds with electron-deficient alkenes or alkynes, this methodology proceeded with a sequential Baylis–Hillman/intramolecular cyclization mechanism and a variety of reversed regioselectivity products were prepared in good

  开发了由甲苯磺酰hydr和硝基烯烃有效合成吡唑的方法。与先前报道的重氮化合物与缺电子的烯烃或炔烃进行的1,3-偶极环加成反应相比，该方法采用了依次的Baylis-Hillman /分子内环化机理，并制备了许多反向的区域选择性产物，收率很高。
• Novel Pyrazole and Indazole Derivatives: Synthesis and Evaluation of Their Anti-Proliferative and Anti-Angiogenic Activities
  作者：Evangelia Tzanetou、Sandra Liekens、Konstantinos M. Kasiotis、Nikolas Fokialakis、Serkos A. Haroutounian

  DOI：10.1002/ardp.201200057

  日期：2012.10

  The synthesis of several new pyrazole and indazole derivatives from acetophenone and tetralone substrates is reported. The bioactivities of the new compounds were evaluated through in vitro assays for endothelial cell proliferation and tube formation. Results herein indicate that the easily prepared compounds containing the indazole structural framework exhibit potent cytostatic properties against

  报道了从苯乙酮和四氢萘酮底物合成几种新的吡唑和吲唑衍生物。通过对内皮细胞增殖和管形成的体外测定来评估新化合物的生物活性。本文的结果表明，含有吲唑结构框架的易于制备的化合物对所有测试的细胞系都表现出有效的细胞抑制特性，其中化合物 13 和 14 是最活跃的，对 MCF 的 IC50 值分别为 1.5 ± 0.4 µM 和 5.6 ± 2.5 µM ‐7 个细胞。此外，吲唑衍生物 16 被评估为 30 µM 内皮管形成的有效抑制剂。