N-(3-{[5-oxo-2-phenyl-1,3-oxazol-4(5H)-ylidene]methyl}phenyl)acetamide | 18692-67-6

• 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: N-(3-{[5-oxo-2-phenyl-1,3-oxazol-4(5H)-ylidene]methyl}phenyl)acetamide
• 英文别名: acetic acid-[4-((Z)-5-oxo-2-phenyl-oxazol-4-ylidenemethyl)-anilide]；Essigsaeure-[4-((Z)-5-oxo-2-phenyl-oxazol-4-ylidenmethyl)-anilid]；N-[4-[(5-oxo-2-phenyl-1,3-oxazol-4-ylidene)methyl]phenyl]acetamide
• CAS: 18692-67-6
• 化学式: C₁₈H₁₄N₂O₃
• 分子量: 306.321
• InChiKey: FAGABTXSCPNPKD-UHFFFAOYSA-N

物化性质

• 熔点：
  237-239 °C(Solv: acetic acid (64-19-7))
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  67.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3-{[5-oxo-2-phenyl-1,3-oxazol-4(5H)-ylidene]methyl}phenyl)acetamide 在 肼 作用下， 以 乙醇 为溶剂， 生成
  参考文献：
  名称：

  萘基N-酰基腙衍生物的合成、分子对接及生物学评价

  摘要：

  通过2-(苯甲酰氨基)缩合合成一系列2-(苯甲酰氨基)-N′-((萘-1-基)亚甲基)-3-(取代苯基)丙烯酰肼(4a-m, 5a-b) -3-（取代苯基）丙烯酰肼与 1-萘醛在乙醇中存在几滴乙酸的情况下。最终化合物的结构解析通过光谱数据得到证实。评估了标题化合物的抗氧化和抗菌活性，并进行了计算机模拟研究和与环氧合酶-II（COX-II，PDB I'd：3LN1）的分子对接研究，并选择对接研究中的活性化合物用于其抗炎活性的体内评估活动。该系列中，化合物4i表现出良好的抗氧化活性；5b显示出良好的抗菌活性。选择所有具有良好对接分数的六种衍生物用于其抗炎活性的体内评估。在对接研究选定的活性化合物中，化合物4m表现出良好的抗炎活性，与标准药物双氯芬酸相当。计算机模拟研究表明，所有化合物均遵循 Lipinski 规则，并表现出良好的口服吸收和生物利用度。

  DOI：

  10.14233/ajchem.2022.23632
• 作为产物：
  描述：

  马尿酸 、 对乙酰氨基苯甲醛 在 sodium acetate 、 乙酸酐 、 PPA 作用下， 反应 2.0h， 以57%的产率得到N-(3-{[5-oxo-2-phenyl-1,3-oxazol-4(5H)-ylidene]methyl}phenyl)acetamide
  参考文献：
  名称：

  Oxazolones: New tyrosinase inhibitors; synthesis and their structure–activity relationships

  摘要：

  The tyrosinase inhibitory potential of seventeen synthesized oxazolone derivatives has been evaluated and their structure-activity relationships developed in the present work. All the synthesized derivatives, 3-19, demonstrated excellent in vitro tyrosinase inhibitory properties having IC50 values in the range of 1.23 +/- 0.37-17.73 +/- 2.69 mu M, whereas standard inhibitors L-mimosine and kojic acid have IC50 values 3.68 +/- 0.02 and 16.67 +/- 0.52 mu M,, respectively. Compounds 4-8 having IC50 values 3.11 +/- 0.95, 3.51 +/- 0.25, 3.23 +/- 0.66, 1.23 +/- 0.37, and 2.15 +/- 0.75, respectively, were found to be very active members of the series, even better than both the standard inhibitors. However, compounds 3, 9-11, 13, 14, 16, 17, and 19 were found to be better than kojic acid but not L-mimosine. (2-Methyl-4-[E,2Z)-3-phenyl-2-propenyliden]-1,3-oxazol-5(4H)-one (7) bearing a cinnamyol residue at C-4 of oxazolone moiety and an IC50 = 1.23 +/- 0.37 mu M was found to be the most active one among all tested compounds. These studies reveal that the substitution of functional group (s) at C-4 and C-2 positions plays a vital role in the activity of this series of compounds. It is concluded that compound 7 may act as a potential lead molecule to develop new drugs for the treatment of tyrosinase based disorders. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.05.014

文献信息

• Oxazolones: New tyrosinase inhibitors; synthesis and their structure–activity relationships
  作者：Khalid Mohammed Khan、Uzma Rasool Mughal、Mahmud Tareq Hassan Khan、Zia-Ullah、Shahnaz Perveen、Muhammad Iqbal Choudhary

  DOI：10.1016/j.bmc.2006.05.014

  日期：2006.9

  The tyrosinase inhibitory potential of seventeen synthesized oxazolone derivatives has been evaluated and their structure-activity relationships developed in the present work. All the synthesized derivatives, 3-19, demonstrated excellent in vitro tyrosinase inhibitory properties having IC50 values in the range of 1.23 +/- 0.37-17.73 +/- 2.69 mu M, whereas standard inhibitors L-mimosine and kojic acid have IC50 values 3.68 +/- 0.02 and 16.67 +/- 0.52 mu M,, respectively. Compounds 4-8 having IC50 values 3.11 +/- 0.95, 3.51 +/- 0.25, 3.23 +/- 0.66, 1.23 +/- 0.37, and 2.15 +/- 0.75, respectively, were found to be very active members of the series, even better than both the standard inhibitors. However, compounds 3, 9-11, 13, 14, 16, 17, and 19 were found to be better than kojic acid but not L-mimosine. (2-Methyl-4-[E,2Z)-3-phenyl-2-propenyliden]-1,3-oxazol-5(4H)-one (7) bearing a cinnamyol residue at C-4 of oxazolone moiety and an IC50 = 1.23 +/- 0.37 mu M was found to be the most active one among all tested compounds. These studies reveal that the substitution of functional group (s) at C-4 and C-2 positions plays a vital role in the activity of this series of compounds. It is concluded that compound 7 may act as a potential lead molecule to develop new drugs for the treatment of tyrosinase based disorders. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis, Molecular Docking and Biological Evaluation of Napthyl N-Acyl Hydrazone Derivatives
  作者：J. Sambrajyam、M. Vidya Rani、G. Rajitha

  DOI：10.14233/ajchem.2022.23632

  日期：——

  antibacterial activities and subjected to in silico studies and molecular docking studies with cyclooxygenase-II (COX-II, PDB I’d: 3LN1) and active compounds from docking studies were selected for in vivo evaluation of their antiinflammatory activity. Among the series, compound 4i showed good antioxidant activity; 5b showed good antibacterial activity. All the six derivatives with good docking scores

  通过2-(苯甲酰氨基)缩合合成一系列2-(苯甲酰氨基)-N′-((萘-1-基)亚甲基)-3-(取代苯基)丙烯酰肼(4a-m, 5a-b) -3-（取代苯基）丙烯酰肼与 1-萘醛在乙醇中存在几滴乙酸的情况下。最终化合物的结构解析通过光谱数据得到证实。评估了标题化合物的抗氧化和抗菌活性，并进行了计算机模拟研究和与环氧合酶-II（COX-II，PDB I'd：3LN1）的分子对接研究，并选择对接研究中的活性化合物用于其抗炎活性的体内评估活动。该系列中，化合物4i表现出良好的抗氧化活性；5b显示出良好的抗菌活性。选择所有具有良好对接分数的六种衍生物用于其抗炎活性的体内评估。在对接研究选定的活性化合物中，化合物4m表现出良好的抗炎活性，与标准药物双氯芬酸相当。计算机模拟研究表明，所有化合物均遵循 Lipinski 规则，并表现出良好的口服吸收和生物利用度。