1-phenyl-3-methyl-4-(2-furancarbonyl)-pyrazol-5-one | 383427-41-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-phenyl-3-methyl-4-(2-furancarbonyl)-pyrazol-5-one
• 英文别名: 1-phenyl-3-methyl-(4-furancarbonyl)-pyrazol-5-one；1-phenyl-3-methyl-4-(2-furanoyl)-pyrazol-5-one；1-phenyl-3-methyl-4-(2-furanoyl)pyrazol-5-one；1-phenyl-3-methyl-4-(2-furoyl)-pyrazole-5-one；1-phenyl-3-methyl-4-(2-furoyl)-pyrazol-5-one；HQfur
• CAS: 383427-41-6
• 化学式: C₁₅H₁₂N₂O₃
• 分子量: 268.272
• InChiKey: IBAWYDNMPWWAHN-UHFFFAOYSA-N

物化性质

• 熔点：
  103-105 °C
• 沸点：
  403.6±40.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.71
• 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：
  0.07
• 拓扑面积：
  68.26
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  1-phenyl-3-methyl-4-(2-furancarbonyl)-pyrazol-5-one 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  摘要：

  Complexes of 1-phenyl-3-methyl-4-thenoylpyrazol-5-one and of 1-phenyl-3-methyl-4-furancarbonylpyrazol-5-one, which was synthesized for the first time, with copper, rhodium, lanthanum, and europium were studied. The substances obtained were studied using, elemental analysis and IR spectroscopy, while the rhodium derivatives were additionally studied using the H-1 NMR method. The thermal stability of the copper derivatives was studied upon heating in a vacuum. The presence of additional heteroatoms in acylpyrazolone had virtually no effect on the structure and composition of the complexes formed. These ligands were shown to coordinate atoms of d and f metals through oxygen atoms similarly to other beta-diketones, whereas the remaining heteroatoms only participated in the formation of a hydrogen bonding system with additional ligands or coordinated solvent molecules.

  DOI：

  10.1023/a:1015220003972

文献信息

• Synthesis, structure and luminescence properties of new rare earth metal complexes with 1-phenyl-3-methyl-4-acylpyrazol-5-ones
  作者：Claudio Pettinari、Fabio Marchetti、Riccardo Pettinari、Andrei Drozdov、Sergei Troyanov、Alexander I. Voloshin、Nail M. Shavaleev

  DOI：10.1039/b108058j

  日期：——

  The isolation and characterization of new lanthanide complexes of formula [Ln(QL)3(EtOH)(H2O)], (Ln = La, Pr, Nd, Sm, Eu, Gd, Tb, Dy, Ho, Er, Tm, Yb; HQL = 1-phenyl-3-methyl-4-phenylacetylpyrazol-5-one) [Ln(QL)3(H2O)2] (L = La or Lu), [Ln(QS)3(EtOH)(H2O)] (Ln = Tb or Eu; HQS = 1-phenyl-3-methyl-4-thienoylpyrazol-5-one, [Tb(QO)3(EtOH)(H2O)] (HQO = 1-phenyl-3-methyl-4-furanoylpyrazol-5-one) [Tb(QF)3(H2O)2]

  新型[Ln（Q L）3（EtOH）（H 2 O）]镧系元素络合物的分离和表征，（Ln = La，Pr，Nd，Sm，Eu，Gd，Tb，Dy，Ho，Er， Tm，Yb; HQ L =1-苯基-3-甲基-4-苯基乙酰基吡唑-5-酮）[Ln（Q L）3（H 2 O）2 ]（L = La或Lu），[Ln（Q S）3（EtOH）（H 2 O）]（Ln = Tb或Eu; HQ S =1-苯基-3-甲基-4-噻吩基吡唑-5-酮，[Tb（Q O）3（EtOH）（H 2 O）]（HQ O =1-苯基-3-甲基-4-呋喃酰基吡唑-5-酮）[Tb（Q F）3（H 2 O）2 ]（HQ F = 1-苯基-3-甲基-4-三氟乙酰基吡唑-5-酮）和[NBu 4 ] [Ln（Q）4 ]（Ln =报告了Eu或Tb，Q = Q F或Q L）。三（β-二酮酸酯）配合物[Nd（Q L）3（EtOH）（H 2 O）]，[Dy（Q L）3（EtOH）（H
• Multitarget-Directed Gallium(III) Tris(acyl-pyrazolonate) Complexes Induce Ferroptosis in Cancer Cells via Dysregulation of Cell Redox Homeostasis and Inhibition of the Mevalonate Pathway
  作者：Daphne Romani、Fabio Marchetti、Corrado Di Nicola、Massimiliano Cuccioloni、Chunmei Gong、Anna Maria Eleuteri、Agustín Galindo、Farzaneh Fadaei-Tirani、Massimo Nabissi、Riccardo Pettinari

  DOI：10.1021/acs.jmedchem.2c01374

  日期：2023.3.9

  cascade, and inhibition of the mevalonate pathway) and induced changes in cell redox homeostasis (decreased levels of GSH/GPX4 and NADP(H), increased reactive oxygen species (ROS) and 4-hydroxynonenal (HNE), mitochondrial damage, and increased activity of CPR and CcO), identifying ferroptosis as the mechanism responsible for cancer cell death.

  合成了一系列Ga(Q n ) 3配位化合物，其中HQ n是 1-phenyl-3-methyl-4-RC(=O)-pyrazolo-5-one。通过分析数据、核磁共振和红外光谱、ESI 质谱、元素分析、X 射线晶体学和密度泛函理论 (DFT) 研究对复合物进行了表征。通过 3-(4,5-二甲基噻唑-2-基)-2,5-二苯基四唑溴化物 (MTT) 测定法测定了针对一组人类癌细胞系的细胞毒活性，在细胞系选择性和与顺铂相比的毒性值。通过分光光度法、荧光测定法、色谱法、免疫测定法和细胞荧光测定法、SPR 生物传感器结合研究和基于细胞的实验探索了作用机制。用镓 (III) 复合物处理细胞可促进多种细胞死亡触发信号（p27、PCNA、PARP 片段的积累，
• Silver(I) derivatives with new functionalised acylpyrazolonates
  作者：Augusto Cingolani、Effendy、Fabio Marchetti、Claudio Pettinari、Riccardo Pettinari、Brian W Skelton、Allan H White

  DOI：10.1016/s0020-1693(01)00812-x

  日期：2002.2

  Silver(I) acylpyrazolonate derivatives of formula [Ag(Q)(R3P)](2) and [Ag(Q)(R3P)(2)](3) (QH = 1-phenyl-3-methyl-4-R'(C=O)-pyrazol-5-one; QdegreesH, R' = furane; Q(S)H, R' = thiophene; R = Ph, Cy, o-tol), have been synthesised and characterised, both in the solid state and in solution. The derivatives [Ag(Q)(R3P)](2) contain dinuclear AgO2NP units with the acylpyrazolonate coordinating in a bridging O,O'-Q-N fashion. The [A-(Q)(R3P)(2)] are tetrahedral species, with the distortion from ideal geometry increasing with the bulk of the phosphine. The [Ag(Q)(R3P)(2)] derivatives are fluxional in chloroform solution when R3P is sterically hindered (R = Cy or o-tol), dissociating partially to the [Ag(Q)(R3P)] fragment and free R,P. [Ag(Q(S))(Ph3P)](2) reacts with 1-methyl-2-mercaptoimidazole (Hmimt) affording the compound [Ag(Hmimt)(Ph3P)(Q(S))] and [Ag(Q(O))(Ph3P)](2) reacts with 1-methyl-imidazole (Meim) affording the compound [Ag(Meim)(Ph3P)(Q(O))], whereas [Ag(Q(S))(Ph3P)](2) reacts with 1,10-phenanthroline (phen), affording the compound [Ag(phen)(Ph3P)](Q(S)). Finally [Ag(Q(S))(Ph3P)(2)] reacts with phen producing the ionic species [Ag(phen)(Ph3P)(2)](Q(S)). (C) 2001 Elsevier Science B.V. All rights reserved.
• Novel triorganotin(IV) complexes of β-diketonates bearing two heterocycles in their structures
  作者：Claudio Pettinari、Fabio Marchetti、Ivan Timokhin、Alessandro Marinelli、Corrado Di Nicola、Brian W. Skelton、Allan H. White

  DOI：10.1016/j.ica.2010.12.002

  日期：2011.2

  Novel triorganotin(IV) derivatives of beta-diketonate Q ligands (HQ in general, in detail HQ(fur) = 1-phenyl-3-methyl-4-(2-furancarbonyl)-pyrazol-5-one, HQ(thi) = 1-phenyl-3-methyl-4-(2-thienylcarbonyl)-pyrazol-5one) of general formula (Q)SnR3 center dot xH(2)O (R = Ph, x = 0; R = Bu-n or Me, x = 1) have been synthesized and spectroscopically and thermally characterized. Triphenyltin(IV) complexes have been isolated as anhydrous compounds while trialkyltin(IV) are always monohydrated. The structures of (Q(fur))SnPh3 and (Q(thi))SnMe3(OH2) are recorded. The tin atoms are five-coordinate in both. In the first, the pyrazolonate ligand behaves as an O,O'-bidentate; there are two similar but independent molecules in the structure. In the quasi-trigonal-bipyramidal environments, Sn-O(acyl) are 2.478(3), 2.364(3), Sn-O(pyrazolonate) 2.050(2), 2.079(2), Sn-C 2.123(4)-2.162(3) angstrom with the longer O(acyl) and a phenyl group quasi-trans (O-Sn-C 162.5(1), 160.8(1)degrees). In (Q(thi)) SnMe3(OH2), the three methyl groups are equatorial (Sn-C 2.1259(9)-2.1380(8) angstrom); Sn-O(Qthi, OH2) are 2.2143(5), 2.3350(6) angstrom, O-Sn-O 175.36(2)degrees. Trimethyltin(IV) derivatives decompose on heating with release of H2O and SnMe4 and formation of (Q)(2)SnMe2. Decomposition occurs also within two days after dissolution of (Q) SnMe3(OH2) in chloroform. (C) 2010 Elsevier B.V. All rights reserved.
• The reactivity of new (1,5-cyclooctadiene)rhodium acylpyrazolonates towards N- and P-donor ligands: X-ray structures of [Rh(1,5-COD)Qs], [Rh(1,5-COD)(phen)]Qs·0.5H2O (HQs=1-phenyl-3-methyl-4-(2-thenoyl)-pyrazol-5-one) and [Rh(1,5-COD)Br]2
  作者：Claudio Pettinari、Fabio Marchetti、Augusto Cingolani、Gianluca Bianchini、Andrei Drozdov、Vyacheslav Vertlib、Sergei Troyanov

  DOI：10.1016/s0022-328x(02)01122-1

  日期：2002.5

  Complexes [Rh(1,5-COD)(Q)] have been prepared by the reaction between [Rh(1,5-COD)Cl](2) (1,5-COD = 1,5-cyclooetadiene) and HQ (where HQ = 1-phenyl-3-methyl-4-R-pyrazol-5-one: R = 2-thenoyl (HQ(s)), 2-furanoyl (HQ(o)) or tert-butylacetyl (HQ(T)). [Rh(1,5-COD)(Q)] react with N-2-donor ligands such as 1,10-phenanthroline (phen) or 2,2-bipyridyl (bipy) yielding ionic compounds [Rh(1,5-COD)(N-2-donor)]Q. The substitutional lability of 1,5-COD in [Rh(1,5-COD)(Q)] versus mono- and di-organophosphine ligands was also investigated. In all cases 1,5-COD has been displaced. Reaction with two equivalents of PPh3 gave, upon oxidation of the Rh(l) centre, [Rh(PPh3)1(01)(Q)l species containing a eta(2)-peroxo-group. Reaction of [Rh(1,5-COD)(Q)] with the chelating P-2-donor 1,2-bis(diphenylphosphino)ethane (dppe) or 4,4'-bis(diphenylphosphino)ferrocene (dppf) yields the peroxo Rh(III) compounds [Rh(dppe)(2)O-2]Q(T) and [Rh(dppf)O-2(Q(T))] or Rh(I) species [Rh(dppf-O-2)(Q(T))] containing the diphosphine in the oxidised form. Finally the reaction between [Rh(1,5-COD)(Q)] and allylbromide yields the well-known [Rh(1,5-COD)Br](2). All complexes have been characterised by analytical and spectral data (IR, H-1 and P-31 ((1)HJ-NMR spectra). The crystal structures of [Rh(1,5-COD)(Q(5))], [Rh(1,5-COD)(phen)]Q(5) and [Rh(1,5-COD)Br](2), all containing a Rh(l) atom in a square coordinate environment, are also reported. (C) 2002 Elsevier Science B.V. All rights reserved.