(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)(thiophen-2-yl)methanone | 188985-49-1

• 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-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)(thiophen-2-yl)methanone
• 英文别名: 5-methyl-2-phenyl-4-<2-thienoyl>-1,2-dihydro-3H-pyrazol-3-one；1-phenyl-3-methyl-(4-thiophenecarbonyl)-pyrazol-5-one；1-phenyl-3-methyl-4-(2-thienylcarbonyl)-pyrazol-5-one；1-phenyl-3-methyl-4-(2-thenoyl)-pyrazole-5-one；1-phenyl-3-methyl-4-(2-thienoyl)-pyrazol-5-one；1-phenyl-3-methyl-4-(2-thienoyl)pyrazol-5-one
• CAS: 188985-49-1
• 化学式: C₁₅H₁₂N₂O₂S
• 分子量: 284.338
• InChiKey: JMMPHCKKMFBETL-UHFFFAOYSA-N

物化性质

• 熔点：
  152-155 °C
• 沸点：
  421.4±40.0 °C(Predicted)
• 密度：
  1.33±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.18
• 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：
  55.12
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)(thiophen-2-yl)methanone 以 乙醇 为溶剂， 生成 Cu[C₆H₅C₃N₂CH₃COC₄H₃SO]2
  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
• 作为产物：
  描述：

  2-噻吩甲酰氯 、 依达拉奉 在 calcium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 反应 4.17h， 生成 (5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)(thiophen-2-yl)methanone
  参考文献：
  名称：

  Disulfide linked pyrazole derivatives inhibit phagocytosis of opsonized blood cells

  摘要：

  Immune thrombocytopenia (ITP) is caused by production of an autoantibody to autologous platelets. ITP can be treated either by reducing platelet destruction or by increasing platelet production. Fc gamma receptor mediated phagocytosis of the opsonized blood cells is a well-accepted mechanism for the underlying pathogenesis of ITP and inhibition of this phagocytosis process with small molecules is a potential strategy for the development of drugs against ITP. A broad screen indicated that 4-methyl-1-phenyl-pyrazole derivative (1) could inhibit the phagocytosis of opsonized blood cells with weak potency. We reveal here the discovery of the polysulfide products, synthesis of various 1-phenyl-pyrazole derivatives, and the biological evaluation of pyrazole derivatives as inhibitors of phagocytosis for potential use as therapeutics for ITP. Substitution at C4 of the pyrazole moiety in the disulfide-bridged dimers influenced the potency in the increasing order of 10 congruent to 11 congruent to 16 < 19 < 20. A novel scaffold, 20 with an IC50 of 100 nM inhibiting opsonized blood cell phagocytosis was identified as a potential candidate for further studies. Confirmation of the disulfide bridge additionally provides clues for the non-thiol or non-disulfide bridge carrying ligands targeting ITP and other similar disorders. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.064

文献信息

• Syntheses, structures, and spectroscopy of mono- and polynuclear lanthanide complexes containing 4-acyl-pyrazolones and diphosphineoxide
  作者：Fabio Marchetti、Claudio Pettinari、Adriano Pizzabiocca、Andrei A. Drozdov、Sergei I. Troyanov、Constantine O. Zhuravlev、Sergey N. Semenov、Yuriy A. Belousov、Ivan G. Timokhin

  DOI：10.1016/j.ica.2010.08.006

  日期：2010.11

  Direct synthesis of oligo- and polymeric Ln complexes with a predicted structure is hampered due to high coordination numbers and unstable coordination polyhedra. A «building blocks» strategy for the synthesis of Ln(Q)3L polymers (Ln = Eu, Tb or Gd; HQ = 1-phenyl-3-methyl-4-RC( O)pyrazol-5-one in general, in detail HQS, R = thienyl; HQCP: R = cyclopentyl; L = bis(diphenylphosphine)methane dioxide

  摘要镧系配位化合物因其独特的发光和磁性而非常重要。由于高配位数和不稳定的配位多面体，阻碍了具有预测结构的低聚和聚合Ln配合物的直接合成。一种合成“ Ln（Q）3L聚合物（Ln = Eu，Tb或Gd； HQ = 1-苯基-3-甲基-4-RC（O）吡唑-5-酮”的“基石”策略），详细信息HQS，R =噻吩基; HQCP：R =环戊基; L =已使用双（二苯基膦）甲烷dppMO2，双（二苯基膦）环氧乙烷dppEO2和双（二苯基膦）丁烷二氧化物dppBO2）：Ln（Q）3 }当X = E或B时，单核片段已通过dppXO2桥连接，而单体分子衍生物已被dppMO2分离。准备了18个新的综合体，它们中的12个显示出聚合性质，而6个是单体。在结构上对三种化合物进行了表征，进一步证实了假设的连通性，其中发现金属中心存在于LnO8方形反棱柱环境中。还研究了发光性质。
• 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
• Synthesis, Characterization and Antibacterial Activities of Manganese(II), Nickel(II), Copper(II) and Zinc(II) Complexes of the Hydrazone Compounds Derived from 1-Phenyl-3-methyl-4-acyl-pyrazole and Benzoyl Hydrazine
  作者：Hualing Zhu、Jinhua Zhu、Chen Chen、Zhen Wei、Lin Tian

  DOI：10.14233/ajchem.2013.14779

  日期：——

  Manganese(II), nickel(II), copper(II) and zinc(II) complexes were prepared by the reactions of the correspondence metal acetate and the hydrazone ligands (L1-L3) derived from 1-phenyl-3-methyl-4-acyl-pyrazole and benzoyl hydrazine. The ligands (L1-L3) and metal complexes were characterized by elemental analysis and spectroscopic techniques such as 1H NMR and IR. Antimicrobial activity studies of (L1-L3) and the metal complexes against Escherichia coli and Bacillus subtilis were carried out by using disc diffusion method. The results indicate that the free ligands are more or less inactive against the two bacteria, the antibacterial abilities of the ligands become more pronounced when they are coordinated to the metal ions. The copper(II) complex of the benzoic acid [1-(5-methyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)ethylidene]hydrazide (L1) shows a significant inhibition to the growth of the two tested bacteria.

  锰（II）、镍（II）、铜（II）和锌（II）配合物是由对应的金属醋酸盐与 1-苯基-3-甲基-4-酰基吡唑和苯甲酰肼衍生的腙配体（L1-L3）反应制备的。配体（L1-L3）和金属配合物通过元素分析以及 1H NMR 和 IR 等光谱技术进行了表征。采用盘扩散法研究了配体（L1-L3）和金属配合物对大肠杆菌和枯草杆菌的抗菌活性。结果表明，游离配体对这两种细菌或多或少没有活性，配体与金属离子配位后，抗菌能力更加明显。苯甲酸 [1-（5-甲基-3-氧代-2-苯基-2,3-二氢-1H-吡唑-4-基）亚乙基]酰肼（L1）的铜（II）配合物对两种受测细菌的生长有明显的抑制作用。
• Lanthanide metal complexes containing the first structurally characterized β-diketonate acid stabilized by hydrogen bonding
  作者：Claudio Pettinari、Fabio Marchetti、Augusto Cingolani、Andrei Drozdov、Sergei Troyanov、Ivan Timokhin、Vyacheslav Vertlib

  DOI：10.1016/s1387-7003(02)00678-0

  日期：2003.1

  Abstract A series of H3O+}[MQs4]− (M=Tb, Eu, Lu; HQs=1-phenyl-3-methyl-4-thenoylpyrazole-5-one) complexes have been prepared and characterized; the presence of the H3O+} cation stabilized by H-bonding to the pyridinic nitrogen of Qs has been confirmed by X-ray and spectroscopic (NMR, IR) investigations.

  摘要 制备并表征了一系列H3O+}[MQs4]− (M=Tb, Eu, Lu; HQs=1-phenyl-3-methyl-4-thenoylpyrazole-5-one)配合物；通过 X 射线和光谱（NMR、IR）研究证实了通过与 Qs 的吡啶氮 H 键合而稳定的 +} 阳离子的存在。
• 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.