1-(4-氯苯基)-3-苯基-2-吡唑-5-酮 | 60798-13-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(4-氯苯基)-3-苯基-2-吡唑-5-酮
• 英文名称: 2-(4-chlorophenyl)-5-phenyl-2,4-dihydro-3H-pyrazol-3-one
• 英文别名: 1-(4-Chlorophenyl)-3-phenyl-2-pyrazolin-5-one；2-(4-chlorophenyl)-5-phenyl-4H-pyrazol-3-one
• CAS: 60798-13-2
• 化学式: C₁₅H₁₁ClN₂O
• 分子量: 270.718
• InChiKey: YHMJWTXJAHETSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  32.7
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(4-氯苯基)-3-苯基-2-吡唑-5-酮 在 三乙胺 作用下， 生成 1-(4-Chloro-phenyl)-4,6,6-trimethyl-3-phenyl-1,6-dihydro-pyrano[2,3-c]pyrazole
  参考文献：
  名称：

  Matsugo, Seiichi; Saito, Mitsuo; Kato, Yohko, Chemical and pharmaceutical bulletin, 1984, vol. 32, # 6, p. 2146 - 2153

  摘要：

  DOI：
• 作为产物：
  描述：

  1-(4-chlorophenyl)-5-ethoxy-3-phenyl-1H-pyrazole 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 36.0h， 以86%的产率得到1-(4-氯苯基)-3-苯基-2-吡唑-5-酮
  参考文献：
  名称：

  Alkoxypyrazoles and the process for their preparation

  摘要：

  本发明涉及一种烷氧基吡唑的制备方法，以及新的烷氧基吡唑化合物。

  公开号：

  EP2151433A1

文献信息

• Enantioselective Copper-Catalyzed [3 + 3] Cycloaddition of Tertiary Propargylic Esters with 1<i>H</i>-Pyrazol-5(4<i>H</i>)-ones toward Optically Active Spirooxindoles
  作者：You-Wei Xu、Ling Li、Xiang-Ping Hu

  DOI：10.1021/acs.orglett.0c03587

  日期：2020.12.18

  A copper-catalyzed enantioselective [3 + 3] cycloaddition of 3-ethynyl-2-oxoindolin-3-yl acetates with 1H-pyrazol-5(4H)-ones for the construction of optically active spirooxindoles bearing a spiro all-carbon quaternary stereocenter has been realized. With a combination of Cu(OTf)2 and chiral tridentate ketimine P,N,N-ligand as the catalyst, the reaction displayed broad substrate scopes, good yields

  铜催化的3-乙炔基-2-氧代吲哚-3-基乙酸乙酸酯与1 H-吡唑-5（4 H）-的铜对映体选择性[3 + 3]环加成反应，用于构建带有螺全碳的旋光螺硫醇四元立体中心已实现。以Cu（OTf）2和手性三齿酮亚胺P，N，N-配体为催化剂，该反应显示出较宽的底物范围，良好的收率和高对映选择性。这代表了使用叔炔丙基酯作为双亲电子试剂进行手性螺环骨架的首次催化不对称炔丙基环加成反应。
• Synthesis, Crystal Structure and Evaluation of Cancer Inhibitory Activity of 4-[indol-3-yl-Methylene]-1<i>H</i>-pyrazol-5(4<i>H</i>)-one derivatives
  作者：Lingling Jing、Liang Wang、Yinglan Zhao、Rui Tan、Xiumei Xing、Ting Liu、Wencai Huang、Youfu Luo、Zicheng Li

  DOI：10.3184/174751912x13501278349974

  日期：2012.12

  series of 4-(1H-indol-3-yl-methylene)-1H-pyrazol-5(4H)-one derivatives have been synthesised. The Z structure of 4-[(1-methyl-1H-indol-3-yl)methylene]-3-phenyl-1-p-tolyl-1H-pyrazol-5-one was determined by X-ray crystallography. The antitumour activity was evaluated against five cancer cells by MTT assay. [(1H-Indol-3-yl)methylene]-1-(2,4-dini-trophenyl)-3-methyl-1H-pyrazole-5-one and 4-4-[(1-benzy

  已经合成了一系列 4-(1H-indol-3-yl-methylene)-1H-pyrazol-5(4H)-one 衍生物。4-[(1-methyl-1H-indol-3-yl)methylene]-3-phenyl-1-p-tolyl-1H-pyrazol-5-one 的 Z 结构由 X 射线晶体学确定。通过 MTT 测定评估了对五种癌细胞的抗肿瘤活性。[(1H-Indol-3-yl)methylene]-1-(2,4-dini-trophenyl)-3-methyl-1H-pyrazole-5-one 和 4-4-[(1-benzyl-1H- indol-3-yl)methylene]-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl}-benzoic acid 对测试癌细胞具有与 5-UF 相似的抗癌活性（除了A375）。几乎所有的目标化合物都对
• Asymmetric [3 + 3] Annulation of Copper–Allenylidenes with Pyrazolones: Synthesis of Chiral 1,4-Dihydropyrano[2,3-<i>c</i>]pyrazoles
  作者：Feng Jiang、Xinping Feng、Rou Wang、Xing Gao、Hao Jia、Yumei Xiao、Cheng Zhang、Hongchao Guo

  DOI：10.1021/acs.orglett.8b02214

  日期：2018.9.7

  The copper-catalyzed asymmetric [3 + 3] annulation of ethynyl benzoxazinanones with pyrazolones has been achieved, providing simple access to 1,4-dihydropyrano[2,3-c]pyrazole derivatives in moderate to excellent yields with excellent enantioselectivities (up to 99% ee). Compared with previous annulation reactions of copper–allenylidenes from ethynyl benzoxazinanones, the current reaction fused the

  乙炔基苯并恶嗪酮与吡唑啉酮的铜催化不对称环化[3 + 3]已实现，可轻松获得1,4-二氢吡喃并[2,3- c ]吡唑衍生物，且产率中等至优异，对映选择性极佳（高达99 ％ee）。与以前的乙炔基苯并恶嗪酮的铜-亚烯基环化反应相比，当前反应将炔丙基部分的三个碳原子融合成杂环骨架。
• Palladium catalysed hydrolysis-free arylation of aliphatic nitriles for the synthesis of 4-arylquinolin-2-one/pyrazolone derivatives
  作者：Singarajanahalli Mundarinti Krishna Reddy、Subramaniyan Prasanna Kumari、Subramaniapillai Selva Ganesan

  DOI：10.1016/j.tetlet.2021.153296

  日期：2021.8

  Palladium catalysed addition of arylboronic acid to the readily available 2-cyano-(N-aryl)-acetamide or ethyl-2-cyanoacetate followed by subsequent reaction transform them into the biologically significant 4-arylquinolin-2-one or pyrazolone derivatives. The reaction conditions are robust enough to prevent the hydrolysis of ester/amide moiety during arylation. In addition, the unactivated nitrile moiety

  钯催化芳基硼酸加成到容易获得的 2-氰基-( N-芳基)-乙酰胺或 2-氰基乙酸乙酯中，随后反应将它们转化为具有生物学意义的 4-芳基喹啉-2-酮或吡唑啉酮衍生物。反应条件足以防止芳基化过程中酯/酰胺部分的水解。此外，乙腈中未活化的腈部分也转化为相应的苯乙酮衍生物。
• Targeting fungal virulence factor by small molecules: Structure-based discovery of novel secreted aspartic protease 2 (SAP2) inhibitors
  作者：Chenglan Li、Yang Liu、Shanchao Wu、Guiyan Han、Jie Tu、Guoqiang Dong、Na Liu、Chunquan Sheng

  DOI：10.1016/j.ejmech.2020.112515

  日期：2020.9

  antifungal target. Using docking-based virtual screening and structure-based inhibitor design, a series of novel SAP2 inhibitors were successfully identified. Among them, indolone derivative 24a showed potent SAP2 inhibitory activity (IC50 = 0.92 μM). It blocked fungi biofilm and hypha formation by down-regulating the expression of genes SAP2, ECE1, ALS3 and EFG1. As a virulence factor inhibitor, compound

  分泌的天冬氨酸蛋白酶2（SAP2）是一种毒性因子，是一种新兴的抗真菌靶标。使用基于对接的虚拟筛选和基于结构的抑制剂设计，成功鉴定了一系列新型SAP2抑制剂。其中，吲哚酮衍生物24a显示出有效的SAP2抑制活性（IC 50 = 0.92μM）。它通过下调SAP2，ECE1，ALS3和EFG1基因的表达来阻止真菌生物膜和菌丝的形成。作为毒力因子抑制剂，化合物24a在体外侵袭性念珠菌病的鼠模型中显示出强效的体内活性。它代表了发现新型抗真菌剂的有前途的先导化合物。