4-(3'-hydroxybenzylidene)-2-phenyl-4-oxazolone | 76505-93-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 4-(3'-hydroxybenzylidene)-2-phenyl-4-oxazolone
• 英文别名: 4-[(3-Hydroxyphenyl)methylidene]-2-phenyl-1,3-oxazol-5-one
• CAS: 76505-93-6
• 化学式: C₁₆H₁₁NO₃
• 分子量: 265.268
• InChiKey: LCCCSMWIDMQSNH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3'-hydroxybenzylidene)-2-phenyl-4-oxazolone 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以70%的产率得到N-[(Z)-1-Hydroxymethyl-2-(3-hydroxy-phenyl)-vinyl]-benzamide
  参考文献：
  名称：

  Rearrangement Reaction of α-Benzoylaminocinnamyl Alcohols

  摘要：

  DOI：

  10.1055/s-1985-31100
• 作为产物：
  描述：

  苯甲酰氯 在 sodium acetate 、 乙酸酐 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 2.0h， 生成 4-(3'-hydroxybenzylidene)-2-phenyl-4-oxazolone
  参考文献：
  名称：

  10.14233/ajchem.2024.31957

  摘要：

  In this study, four different 4-arylidene-2-phenyloxazol-5(4H)-ones (5a-d), were synthesized via the Erlenmeyer-Plöchl reaction and characterized by FT-IR, 1H NMR, 13C NMR and mass spectroscopic techniques. Evaluation of their in vitro anti-inflammatory activities using the heat-induced human red blood cell (HRBC) membrane stabilization assay revealed concentration dependent inhibitory effects. The IC50 values of 5a, 5b, 5c and 5d were reported as 4.65 ± 0.22 mM, 7.34 ± 0.28 mM, 5.23 ± 0.18 mM and 1.96 ± 0.09 mM, respectively. O-Acetyl salicylic acid as standard showed its IC50 value at 6.41 ± 0.18 mM. Docking studies against human cyclooxygenase (COX) 1 and 2 revealed affinities of the compounds to binding cavities of COX enzymes. Particularly, compound 5d exhibited remarkable activity in both HRBC membrane stabilization and the formation of hydrogen bonds with binding cavities. This suggests a potential correlation between the number of hydroxyl groups of oxazolone derivatives and the enhancement of anti-inflammatory activity.

  DOI：

  10.14233/ajchem.2024.31957

文献信息

• Synthesis, Characterization and Biological Activity of 5-Arylidene-3-(6,7-dicloro-1,3-benzothiazol-2-yl)-phenyl-3,5-dihydro-4<i>H</i>-imidazol-4-ones
  作者：B. B. Baldaniya

  DOI：10.1155/2010/264036

  日期：——

  Some novel 5-arylidene-3-(6,7-dichloro-1,3-benzothiazol-2-yl)-2-phenyl-3,5-dihydro-4H-imidazol-4-ones (6a-q)have been synthesized and characterized by elemental analyses, IR, NMR, and mass spectra. The products have been evaluated for antibacterial and antifungal activities against different strains of bacteria and fungi.

  一些新型的5-芳基亚醛基-3-(6,7-二氯-1,3-苯并噻唑-2-基)-2-苯基-3,5-二氢-4H-咪唑-4-酮 (6a-q)已经合成并通过元素分析、红外光谱、核磁共振和质谱进行了表征。这些产物已经针对不同菌株的细菌和真菌进行了抗菌和抗真菌活性评价。
• Sulfanilic Acid-Catalyzed Green Synthesis of 4-Arylidene-2-phenyl-5(4H)-oxazolones
  作者：Hamzeh Kiyani、Shiva Aslanpour

  DOI：10.3987/com-17-13847

  日期：——
• Synthesis of Erlenmeyer-Plöchl Azlactones Promoted by 5-Sulfosalicylic Acid
  作者：Hamzeh Kiyani、Shiva Aslanpour

  DOI：10.3987/com-17-13711

  日期：——

  5-Sulfosalicylic acid was found as an efficient catalyst in the synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones by condensation and cyclodehydration of aromatic aldehydes with hippuric acid and acetic anhydride at room temperature. The catalyst was easily recycled from the filtrate via evaporation of solvent and reused. This process is green, simple to handle, commercially available starting materials and catalyst, mild conditions, as well as it does not require to hazardous organic solvents, heating, and microwave and ultrasound irradiations.
• Upadhyay; Pandya; Parekh, Journal of the Indian Chemical Society, 1991, vol. 68, # 5, p. 296 - 298
  作者：Upadhyay、Pandya、Parekh

  DOI：——

  日期：——
• Trivedi; Kubawat; Parekh, Journal of the Indian Chemical Society, 2002, vol. 79, # 3, p. 282 - 283
  作者：Trivedi、Kubawat、Parekh

  DOI：——

  日期：——