3-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylazo)pentane-2,4-dione | 26304-27-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylazo)pentane-2,4-dione
• 英文别名: 1-phenyl-2,3-dimethyl-5-pyrazolone-4-acetylacetone；3-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylazo)-pentane-2,4-dione；3-[(2,3-Dihydro-1,5-dimethyl-3-oxo-2-phenyl-1h-pyrazol-4-yl)azo]-2,4-pentanedione；3-[(1,5-dimethyl-3-oxo-2-phenylpyrazol-4-yl)diazenyl]pentane-2,4-dione
• CAS: 26304-27-8
• 化学式: C₁₆H₁₈N₄O₃
• 分子量: 314.344
• InChiKey: CNVYOZQTLPVEKM-UHFFFAOYSA-N

物化性质

• 熔点：
  180 °C(Solv: ethanol (64-17-5))
• 沸点：
  404.0±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  82.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylazo)pentane-2,4-dione 在 一水合肼 作用下， 以 溶剂黄146 为溶剂， 生成 4-[(3,5-dimethyl-1H-pyrazol-4-yl)diazenyl]-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one
  参考文献：
  名称：

  Farghaly; El-Khwass; Khalil, Pharmazie, 1981, vol. 36, # 2, p. 93 - 95

  摘要：

  DOI：
• 作为产物：
  描述：

  4-氨基安替比林 、 乙酰丙酮 在 1) diazotation 作用下， 生成 3-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-ylazo)pentane-2,4-dione
  参考文献：
  名称：

  新型 2-Pyrazolyl-4 (3H)-Quinazolinones 的非甾体抗炎药合成

  摘要：

  通过3-芳基-2-肼基-4(3H)-喹唑啉酮与乙酰乙酸乙酯、乙酰丙酮或丙二酸二乙酯的反吡唑啉酮衍生物反应，制备了四个新型吡唑基-4(3H)-喹唑啉酮系列。这些系列的化合物是 3-aryl-2- [1-ethoxycarbonyl-1- (1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl) hydrazono-2 -亚丙基]肼基-4(3H)-喹唑啉酮；3-芳基-2-[4-(4,5-二甲基-3-氧代-2-苯基-2,3-二氢-1H-吡唑-4-基) hydrazono-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl] -4 (3H) -quinazolinones; 3-芳基-2-[4-(1,5-二甲基-3-氧代-2-苯基-2,3-二氢-1H-吡唑-4-基)偶氮-3,5-二甲基-1H-吡唑- 1-基]

  DOI：

  10.1002/ardp.19903231004

文献信息

• Design, synthesis and evaluation of some pyrazolo[3,4-d]pyrimidines as anti-inflammatory agents
  作者：Gina N. Tageldin、Salwa M. Fahmy、Hayam M. Ashour、Mounir A. Khalil、Rasha A. Nassra、Ibrahim M. Labouta

  DOI：10.1016/j.bioorg.2018.03.030

  日期：2018.8

  New pyrazolo[3,4-d]pyrimidines substituted with various functionalities or attached to a substituted pyrazole ring through different linkages were synthesized. The synthesized compounds were evaluated for their anti-inflammatory activity using in vitro COX-1/COX-2 inhibition assay and in vivo formalin induced paw edema and cotton pellet-induced granuloma assays. Results revealed that compounds 17b

  合成了新的吡唑并[3，4- d ]嘧啶，它们被各种官能团取代或通过不同的键连接到取代的吡唑环上。使用体外COX-1 / COX-2抑制试验，体内福尔马林诱导的爪水肿和棉丸诱导的肉芽肿试验评估合成的化合物的抗炎活性。结果表明，化合物17b和18的COX-1 / COX-2选择性指数高于双氯芬酸钠和塞来昔布。但是，化合物16a，b的选择性指数高于双氯芬酸钠，几乎等于塞来昔布，而9b显示的选择性指数可与双氯芬酸钠相媲美。体内抗炎数据显示，化合物9b，16a，18在福尔马林诱发的爪水肿模型中显示出的抗炎活性均高于两个参考文献。另一方面，在棉丸诱导的肉芽肿试验中，吡唑基衍生物9b，16b和17b的抗炎活性约为双氯芬酸钠的2–2.5倍，而塞来昔布的抗炎活性约为8–10.5倍。还研究了活性化合物的致溃疡作用，结果表明化合物16a，17a，b和18具有良好的胃肠道安全性。基于此，化合物16a和18个被认为
• Non-Steroidal Antiinflammatory Agents Synthesis of Novel 2-Pyrazolyl-4(3H)-Quinazolinones
  作者：A. M. Farghaly、I. Chaaban、M. A. Khalil、A. A. Bekhit

  DOI：10.1002/ardp.19903231004

  日期：——

  [4‐(4,5‐dimethyl‐3‐oxo‐2‐phenyl‐2,3‐dihydro‐1H‐pyrazol‐4‐yl)hydrazono‐3‐methyl‐5‐oxo‐4,5‐dihydro‐1H‐pyrazol‐1‐yl]‐4(3H) ‐quinazolinones; 3‐aryl‐2‐[4‐(1,5‐dimethyl‐3‐oxo‐2‐phenyl‐2,3‐dihydro‐1H‐pyrazol‐4‐yl)azo‐3,5‐dimethyl‐1H‐pyrazol‐1‐yl]‐4(3H)‐quinazolinones and 3‐aryl‐2‐[4‐(1,5‐dimethyl‐3‐oxo‐2‐phenyl‐2,3‐dihydro‐1H‐pyrazol‐4‐yl)hydrazono‐3,5‐dioxo‐pyrazolidin‐2‐yl]‐4(3H)‐quinazolinones. The antiinflammatory

  通过3-芳基-2-肼基-4(3H)-喹唑啉酮与乙酰乙酸乙酯、乙酰丙酮或丙二酸二乙酯的反吡唑啉酮衍生物反应，制备了四个新型吡唑基-4(3H)-喹唑啉酮系列。这些系列的化合物是 3-aryl-2- [1-ethoxycarbonyl-1- (1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl) hydrazono-2 -亚丙基]肼基-4(3H)-喹唑啉酮；3-芳基-2-[4-(4,5-二甲基-3-氧代-2-苯基-2,3-二氢-1H-吡唑-4-基) hydrazono-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-1-yl] -4 (3H) -quinazolinones; 3-芳基-2-[4-(1,5-二甲基-3-氧代-2-苯基-2,3-二氢-1H-吡唑-4-基)偶氮-3,5-二甲基-1H-吡唑- 1-基]
• Synthesis, characterization and electrochemical properties of β-diketone complexes of ruthenium(III)
  作者：Fathy A. El-Saied、Ramadan M. El-Bahnasawy、Magdi Abdel Azzem、Ayman K. El-Sawaf

  DOI：10.1016/s0277-5387(00)80110-2

  日期：1994.6

  azo form. The complexes were characterized using a variety of analytical, spectral, magnetic and thermal measurements. The electrochemical redox properties of complexes I–V have been studied by cyclic voltammetry in acetonitrile. The chloro-bridged dimer complexes I–IV showed two reversible diffusion-controlled oxidation peaks. The first was attributed to the oxidation of the ruthenium(III) to the corresponding

  氯化钌（III）（1 mol）与乙酰基乙炔基4-氨基安替比林（HL 1），单苯甲酰基乙酰基乙炔基-4-氨基安替比林（HL 2），二苯甲酰基亚甲叉基-4-氨基安替比林（HL 3）和安替比林-4-偶氮-β的反应-乙酰乙酸乙酯（HL 4）（1 mol）生成通式RuHLCl 3的配合物。配体安替比林-4-偶氮-β -乙酰丙酮（HL 5）（1摩尔）与发生反应的RuCl 3 ·3H 2 O操作产生RUL 5氯2（H 2 O）·H 2 O.配体HL 1 -HL 3作为酮烯胺形式的中性二齿发生反应，而HL 4作为肼基形式的中性二齿发生反应。HL 5作为偶氮形式的一元三齿反应。使用各种分析，光谱，磁和热测量对复合物进行表征。通过循环伏安法在乙腈中研究了配合物IV的电化学氧化还原特性。氯桥二聚体I–IV显示两个可逆的扩散控制的氧化峰。第一个归因于钌（III）被氧化为相应的混合价络合物，第二个归因于钌（IV）络
• New Azo Derivative of β‐Diketones and Its Cu(II), Co(II) Complexes: Synthesis, Theoretical Study and Biological Activity
  作者：Shahla Tahirli、Nastaran Sadeghian、Farqana Aliyeva、Afsun Sujayev、Sevilay Günay、Yavuz Erden、Namig Shikhaliyev、Savaş Kaya、Eda Mehtap Özden、Famil Chiragov、Avni Berisha、Parham Taslimi

  DOI：10.1002/cbdv.202301861

  日期：2024.4

  on 4-amino antipyrine and its complexes with Cu(II), Co(II) in solution and solid phase is reported. The structures of these compounds have been testified by X-ray, IR and NMR spectroscopy. The combined experimental and theoretical approach was used. To study the structure and properties of the synthesized compound, as well as its possible complex formation with the Cu(II), quantum-chemical calculations

  本论文主要对新型β-二酮偶氮衍生物及其与某些金属的配合物的生物活性及结构和性能进行理论研究。我们工作的目的是研究新合成化合物的结构和性质，并从理论上确定与 Cu(II) 或 Co(II) 离子形成络合物的可能性。选择具有相同取代基R 1 =R 2 =CH 3的化合物进行研究。合成了基于4-氨基安替比林的偶氮化合物及其与Cu(II)、Co(II)的溶液和固相配合物。这些化合物的结构已通过X射线、IR和NMR光谱证实。使用了实验和理论相结合的方法。为了研究合成化合物的结构和性质，以及其与Cu(II)可能形成的络合物，采用6-31G基组和电子密度泛函理论(DFT)方法进行了量子化学计算。这些 3-(1-苯基-2,3-二甲基-吡唑啉酮-5)偶氮戊二酮-2,4 (PDPA) 与 Cu(II) 和 Co(II) 络合物对丁酰胆碱酯酶和乙酰胆碱酯酶具有有效的抑制作用。 AChE 的 IC 50值分别为 19
• Synthesis and pharmacological evaluation of new pyrazolyl benzenesulfonamides linked to polysubstituted pyrazoles and thiazolidinones as anti-inflammatory and analgesic agents
  作者：Hayam M. A. Ashour、Ibrahim M. El-Ashmawy、Aida E. Bayad

  DOI：10.1007/s00706-015-1549-x

  日期：2016.3

  New compounds comprising the pyrazolyl benzenesulfonamide scaffold linked to polysubstituted pyrazoles and thiazolidinones were synthesized and evaluated for their anti-inflammatory and analgesic activities. The results revealed that most of the compounds displayed distinctive anti-inflammatory and analgesic activity. Two thiazolidinone derivatives emerged with the highest anti-inflammatory activity in this study, whereas two pyrazole derivatives displayed high analgesic activity with a fast onset of action compared to the reference drug. Moreover, the active compounds showed minimal potential for gastric injury in addition to a good safety margin (ALD(50) >0.25 g/kg). In vitro COX-1/COX-2 inhibition study revealed that the most active compounds showed relatively more selectivity toward COX-2 than COX-1. Among the test compounds, a thiazolidinone derivative possessed the lowest IC50 value against both COX-1 and COX-2.[GRAPHICS].