4-benzoyl-3-methyl 1-phenylpyrazolone-5 sodium salt | 127718-85-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-benzoyl-3-methyl 1-phenylpyrazolone-5 sodium salt
• 英文别名: (4-benzoyl-3-methyl-1-phenylpyrazol-5-onato)sodium
• CAS: 127718-85-8
• 化学式: C₁₇H₁₃N₂O₂*Na
• 分子量: 300.292
• InChiKey: RFXMGHAUPIVJPG-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.51
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  57.95
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  4-benzoyl-3-methyl 1-phenylpyrazolone-5 sodium salt 、 二环己基二溴化锡 以 苯 为溶剂， 生成 dicyclohexylbis[1-phenyl-3-methyl-4-benzoylpyrazolon-5-ato]tin(IV)
  参考文献：
  名称：

  Tin(IV) and organotin(IV) derivatives of anionic 4-acyl-5-pyrazolonato ligands: synthesis, spectroscopic characterization (IR, far-IR, 119Sn mössbauer, 1H, 13C and 119Sn NMR) and behavior in solution crystal and molecular structure of trans-diphenylbis[1-phenyl-3-methyl-4-(4-bromobenzoyl) -pyrazolon-5-ato]tin(IV)

  摘要：

  Stable six-coordinate tin(IV) and organotin(IV) derivatives X(2)SnQ(2) (X = Me, Ph, benzyl, cyclohexyl, Cl or (1)Bu) (QH = 1-R'-3-methyl-4-R ''(C = O)-pyrazol-5-one in general; in detail Q'H: R' = C6H5, R '' = C6H5; Q '' H: R' = C6H5, R '' = CH3; Q(A)H: R' = C6H5, R '' = p-CH3O-C6H4; Q(Br)H: R' = C6H5, R '' = p-Br-C6H4) have been synthesized and characterized by analysis and spectral (IR and far-IR, H-1, C-13 and Sn-119 NMR, Sn-119 Mossbauer) data, Structural predictions were derived from Sn-119 NMR parameters such as (1)J((119Sn-13C)), (2)J((119Sn-1H)) and delta(Sn-119). The diffraction study of the complex [Ph(2)Sn(Q(Br))(2)] shows the metal to be six-coordinate in a skewed trapezoidal bipyramidal geometry; Sn-O distances are 2.12(1) and 2.143(7) Angstrom, and 2.223(8) and 2.26(1) Angstrom and the Ph-Sn-Ph bond angle is 173.0(7)degrees.

  DOI：

  10.1016/s0022-328x(96)06178-5
• 作为产物：
  描述：

  4-苯甲酰基-3-甲基-1-苯基-2-吡唑-5-酮 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以90%的产率得到4-benzoyl-3-methyl 1-phenylpyrazolone-5 sodium salt
  参考文献：
  名称：

  Inhibitory effect of β-diketones and their metal complexes on TNF-α induced expression of ICAM-1 on human endothelial cells

  摘要：

  Recent reports show that the natural beta-diketone curcumin displays important biological properties regarding the intercellular adhesion molecule-1 (ICAM-1), which plays a critical role in the immune responses and inflammation. In this study the ICAM-1 inhibitory activity of beta-diketone compounds, which are curcumin models lacking aromatic peripheral hydroxyl and methoxy groups, along with some metal derivatives is investigated. beta-Diketones are systematically more active than metal complexes and the best obtained inhibition is 75% for both groups. The best inhibitors are 4-benzoyl-3-methyl-1-phenyl-pyrazol- 5-one (HQ(Ph)) among the ligands, and sodium benzoylacetonato among metal derivatives. These results appear in line with the reported antitumor activity of related species. Since 4-acyl-5-pyrazolones posses four tautomeric forms, those corresponding to HQ(Ph) were investigated using density functional theory. Docking of all HQ(Ph) tautomers on ICAM-1 protein was performed suggesting one keto-enol form favored to act in biological environment. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.064

文献信息

• (4‐Acyl‐5‐pyrazolonato)titanium Derivatives: Oligomerization, Hydrolysis, Voltammetry, and DFT Study
  作者：Francesco Caruso、Lou Massa、Asta Gindulyte、Claudio Pettinari、Fabio Marchetti、Riccardo Pettinari、Massimo Ricciutelli、Juan Costamagna、Juan Carlos Canales、Joseph Tanski、Miriam Rossi

  DOI：10.1002/ejic.200300135

  日期：2003.9

  Twenty 4-acyl-5-pyrazolonato (Q) titanium derivatives of varied nuclearity have been synthesized from Ti(OR)4 or TiCl4 and characterized with spectroscopic methods (IR, NMR, ESI-MS). While Ti−(β-diketonato) cleavage is not seen in isolated solids, Ti−O(alkoxy) (or Ti−Cl) bonds cleave upon hydrolysis, leading to several structural forms, including oligomers. Ionic Q species with no Ti, i.e., obtained

  已经从 Ti(OR)4 或 TiCl4 合成了 20 种不同核度的 4-acyl-5-pyrazolonato (Q) 钛衍生物，并用光谱方法（IR、NMR、ESI-MS）进行了表征。虽然在孤立的固体中看不到 Ti-（β-二酮）裂解，但 Ti-O（烷氧基）（或 Ti-Cl）键在水解时裂解，导致多种结构形式，包括低聚物。通过 ESI-MS 可以看到一些 Ti-Q 衍生物没有 Ti，即在 Ti-Q 裂解后获得的离子 Q 物种，这也表明给定物种的核度不同，例如，孤立的多核 [Q2Ti-μ- O]n 有几个“n”值。单核钛配合物是在严格的无水条件下获得的。已使用 DFT 方法分析了单核物质 (QT)2Ti(OCH3)2、QT = 3-methyl-4-(neopentylcarbonyl)-1-phenylpyrazol-5-onato 的顺式结构。反式影响是解释几组 Ti-O 键的主要驱动力。顺式立体异构体之一的能量比其他两种高
• Synthesis, spectra and biological activity of some new telluronium heterocyclic β-diketonates
  作者：K.Maruthi Prasad、N. Rama Rao、M.C. Ganorkar、C.Manohara Chary

  DOI：10.1016/0022-328x(89)88074-x

  日期：1989.10
• Jain, A; Saxena, S; Rai, A K, Indian Journal of Chemistry, Section A: Inorganic, Physical, Theoretical and Analytical, 1991, vol. 30, # 10, p. 881 - 885
  作者：Jain, A、Saxena, S、Rai, A K

  DOI：——

  日期：——
• Organotin(IV) derivatives of acylpyrazol-5-ones
  作者：M.F. Mahon、K.C. Molloy、B.A. Omotowa、M.A. Mesubi

  DOI：10.1016/0022-328x(95)05906-6

  日期：1996.4

  The synthesis and characterization of triorganotin(IV) derivatives of two 4-acylpyrazol-5-ones(4-acetyl-5-one (HPMAP) and 4-benzoyl-5-one (HPMBP)) and of four 1-acylpyrazol-5-ones (1-acetyl-5-one (APzH), 1-(4'-nitrobenzoyl)-5-one (NPzH) and 1-salicyloyl-5-one (SPzH)) as well as those of diorganotin(IV) derivatives of the three 1-acylpyrazol-5-ones are reported. The X-ray crystal structure of tributyl(4-benzoylpyrazol-5-onato)tin(IV) monohydrate is also described.