5-methyl-2-phenyl-4-propanoyl-1H-pyrazol-3-one | 94741-08-9

• 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-methyl-2-phenyl-4-propanoyl-1H-pyrazol-3-one
• 英文别名: 4-propanoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-one；5-methyl-2-phenyl-4-propionyl-1,2-dihydro-3H-pyrazol-3-one；1-phenyl-3-methyl-4-propenylidene-5-pyrazolone；1-phenyl-3-methyl-4-propionyl-pyrazolone-5；3-methyl-1-phenyl-4-propionyl-5-pyrazolone；4-propanoyl-1-phenyl-3-methylpyrazolone-5；4-propionyl-3-methyl-1-phenylpyrazolone-5
• CAS: 94741-08-9
• 化学式: C₁₃H₁₄N₂O₂
• 分子量: 230.266
• InChiKey: HXMPEMJPEGPOPB-UHFFFAOYSA-N

物化性质

• 沸点：
  371.8±37.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.48
• 重原子数：
  17.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  55.12
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-methyl-2-phenyl-4-propanoyl-1H-pyrazol-3-one 在 sodium acetate 、 sodium 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 15.08h， 生成
  参考文献：
  名称：

  基于生物活性杂化材料的从头统一强大的抗糖尿病药效团：DFT辅助设计、优化的分子结构和抗糖尿病生物测定机制的理解

  摘要：

  通过光谱证据和 DFT（B3LYP 方法）合理设计、生成和表征基于混合材料的从头统一的强大抗糖尿病药效团。这些混合药效团表现出强大的抗糖尿病活性。缩氨基脲用于生成这些混合药效基团。杂环β-二酮缩氨基脲通过常规加热以及绿色方法（微波加热）合成。对这两种方法获得的结果进行了总结和比较。将二甲基锡(IV)部分掺入杂环β-二酮的一些缩氨基脲中导致形成Me 2 SnLA类型的生物活性二甲基锡(IV)制剂，其中LH 2  =  , R = -CH 3 , L(1) H 2，配合物1；R = -CH 2 CH 3，L (2) H 2，配合物2；R = -C 6 H 5，L (3) H 2，配合物3；R = p-ClC 6 H 4 -，L (4) H 2，络合物 4。杂环 β-二酮的一种代表性缩氨基脲 (L (4) H 2 ) 及其相应的二甲基锡 (IV) 络合物 Me 2 SnL (4 ）（复合体 4）

  DOI：

  10.1002/aoc.7205

文献信息

• Synthesis, crystal structure and biological activity of two Mn complexes with 4-acyl pyrazolone derivatives
  作者：Yue Li、Jing Zhao、Chuan-Chuan He、Li Zhang、Su-Rong Sun、Guan-Cheng Xu

  DOI：10.1016/j.jinorgbio.2015.06.003

  日期：2015.9

  In order to study the biological activities of transitional metal complexes based on 4-acyl pyrazolone derivatives, two Mn complexes [Mn(HLa)(La)]·(CH3CN)1.5·H2O (1) and [Mn2(Lb)2(μ-EtO)2(EtOH)2] (2) (H2La = N-(1-phenyl-3-methyl-4-benzoyl-5-pyrazolone)-2-thiophenecarboxylic acid hydrazide, H2Lb = N-(1-phenyl-3-methyl-4-propenylidene-5-pyrazolone)-2-thiophenecarboxylic acid hydrazide) have been synthesized

  为了研究基于4-酰基吡唑啉酮衍生物的过渡金属配合物的生物活性，使用两种Mn配合物[Mn（HL a）（L a）]·（CH 3 CN）1.5 ·H 2 O（1）和[Mn 2（L b）2（μ- EtO）2（EtOH）2 ]（2）（H 2 L a  = N-（1-苯基-3-甲基-4-苯甲酰基-5-吡唑啉酮）-2-噻吩羧酸酰肼，H 2 L b ＝已经合成并表征了N-（1-苯基-3-甲基-4-丙烯基亚丙基-5-吡唑啉酮）-2-噻吩羧酸酰肼）。单晶X射线衍射分析表明，1是单核络合物，2是双核中心对称结构。配合物与鲱鱼精子DNA（HS-DNA）的结合表明，配合物1和2可以插入到DNA中，其淬灭常数分别为5.3×10 4  M -1和4.9×10 4  M -1。配合物与牛血清白蛋白（BSA）的相互作用表明配合物1和2可以在静态猝灭过程中猝灭BSA的固有荧光。此外，通过MTT法测定了该复合物对人食道癌Eca
• Tin( <scp>II</scp> ) and Lead( <scp>II</scp> ) 4‐Acyl‐5‐pyrazolonates: Synthesis, Spectroscopic and X‐ray Structural Characterization
  作者：Claudio Pettinari、Fabio Marchetti、Riccardo Pettinari、Augusto Cingolani、Eleonora Rivarola、Christine Phillips、Joseph Tanski、Miriam Rossi、Francesco Caruso

  DOI：10.1002/ejic.200400225

  日期：2004.9

  β-diketonate Sn(Q)2 complexes [HQ = 1-R1-3-R3-4-R4(C=O)-pyrazol-5-one; HQC: R1 = Ph, R3 = Me, R4 = Cy; HQS: R1 = Ph, R3 = Me, R4 = CHPh2; HQL: R1 = Ph, R3 = Me, R4 = CH2Ph; HQT: R1 = Ph, R3 = Me, R4 = CH2tBu; HQE: R1 = Ph, R3 = Me, R4 = Et; HQB: R1 = Ph, R3 = Me, R4 = tBu; HQW: R1 = Ph, R3 = Me, R4 = p-(tBu)Ph; HQR: R1 = Ph, R3 = Me, R4 = p-[(CH2)5CH3]Ph; HQN: R1 = p-NO2Ph, R3 = Me, R4 = Ph; HQM: R1 =

  新型锡 (II) β-二酮 Sn(Q)2 配合物 [HQ = 1-R1-3-R3-4-R4(C=O)-pyrazol-5-one; HQC：R1 = Ph，R3 = Me，R4 = Cy；HQS：R1 = Ph，R3 = Me，R4 = CHPh2；HQL：R1 = Ph，R3 = Me，R4 = CH2Ph；HQT：R1 = Ph，R3 = Me，R4 = CH2tBu；HQE：R1 = Ph，R3 = Me，R4 = Et；HQB：R1 = Ph，R3 = Me，R4 = tBu；HQW：R1 = Ph，R3 = Me，R4 = p-(tBu)Ph；HQR：R1 = Ph，R3 = Me，R4 = p-[(CH2)5CH3]Ph；HQN：R1 = p-NO2Ph，R3 = Me，R4 = Ph；HQM：R1 = Me，R3 = Me，R4 = Ph；总部：R1 = 我，R3 = 我，R4
• Synthesis, Spectroscopic, and X-Ray Diffraction Studies ofcis-Dichlorobis(4-propanoyl-2,4-dihydro-5-methyl-2-phenyl3 H-pyrazol-3-onato) Tin(IV)
  作者：Bieluonwu A. Uzoukwu、Karsten Gloe、Michael Menzel、Otto Rademacher

  DOI：10.1002/1521-3749(200101)627:1<103::aid-zaac103>3.0.co;2-5

  日期：2001.1

  Reaction between an aqueous ethanol solution of tin(II) chloride and that of 4-propanoyl-2,4-dihydro-5-methyl-2-phenyl-3 H-pyrazol-3-one in the presence of O2 gave the compound cis-dichlorobis(4-propanoyl-2,4-dihydro-5-methyl-2-phenyl-3 H-pyrazol-3-onato) tin(IV) [(C26H26N4O4)SnCl2]. The compound has a six-coordinated SnIV centre in a distorted octahedral configuration with two chloro ligands in cis

  在 O2 存在下，氯化锡 (II) 的乙醇水溶液与 4-丙酰基-2,4-二氢-5-甲基-2-苯基-3 H-吡唑-3-one 的乙醇水溶液反应得到化合物顺式-二氯双（4-丙酰基-2,4-二氢-5-甲基-2-苯基-3H-吡唑-3-onato）锡（IV）[（C26H26N4O4）SnCl2]。该化合物具有扭曲八面体构型的六配位 SnIV 中心，在顺式位置有两个氯配体。对于配体阴离子和两个顺式氯配体，锡原子也处于假双反转轴上。橙色化合物在具有晶胞尺寸的三斜空间群 P 1 中结晶，a = 8.741 (3) A，b = 12.325 (7) A，c = 13.922 (7) A；= 71.59 (4), = 79.39 (3), = 75.18 (4); Z = 2 和 Dx = 1,575 g cm-3。螯合环中的重要键距是 Sn-O [2.041 至 2.103 A]、Sn-Cl [2.347 至
• Uzoukwu, B. A.; Gloe, K.; Duddeck, H., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1998, vol. 37, # 11, p. 1180 - 1183
  作者：Uzoukwu, B. A.、Gloe, K.、Duddeck, H.

  DOI：——

  日期：——
• Cytotoxicity of Ruthenium–Arene Complexes Containing β-Ketoamine Ligands
  作者：Riccardo Pettinari、Claudio Pettinari、Fabio Marchetti、Catherine M. Clavel、Rosario Scopelliti、Paul J. Dyson

  DOI：10.1021/om301115e

  日期：2013.1.14

  New ruthenium(II) arene derivatives (arene = p-cymene, benzene, hexamethylbenzene) containing beta-ketoamine ligands L' (HL' in general; in detail, HLph,ph = (4Z)-3-methyl-4-((phenylamino)(phenyl)methylene)-1-phenyl-1H-pyrazol-5(4H)-one, HLnaph,ph = (4Z)-3-methyl-4-((phenyamino)(naphthalen-2-yl)methylene)-1-phenyl-1H-pyrazol-5(4H)- one, HLet,ph = (4Z)-3-methyl-4-(1-(phenylamino)propylidene)-1-phenyl-1Hpyrazol-5(4H)-one) have been synthesized and characterized by spectroscopy (IR, ESI-MS, H-1 and C-13 NMR) and elemental analysis. The ligands in the anionic form coordinate ruthenium in a chelating kappa N-2,O-bidentate fashion, affording 1:1 derivatives of the formula [Ru(arene)(L')Cl]. Further reaction of [Ru(p-cymene)(L')Cl] with AgPF6 or PTA (PTA = 1,3,5-triaza-7-phosphaadamantane) in methanol affords [Ru(p-cymene)(L')(CH3OH)] [PF6] and [Ru(p-cymene) (L')(PTA)]Cl, respectively. The solid-state structures of the ligand HLet,ph and complexes [Ru(p-cymene)(L-ph,L-ph)Cl] (1), [Ru(p-cymene)(L-naph,L-ph)Cl] (4), and [Ru(p-cymene)(L-et,L-ph)Cl] (7) have been determined by single-crystal X-ray diffraction. The antitumor activity of both the ligands and complexes has been evaluated against the human ovarian carcinoma cell line A2780 and its cisplatin-resistant equivalent A2780R, some of the complexes showing significant cytotoxicity toward the cisplatin-resistant cell line.

表征谱图