N-(3-acetylphenyl)-2-phenylacetamide | 72116-69-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(3-acetylphenyl)-2-phenylacetamide
• CAS: 72116-69-9
• 化学式: C₁₆H₁₅NO₂
• mdl: MFCD01359400
• 分子量: 253.301
• InChiKey: FOTVDRUNXUCUIZ-UHFFFAOYSA-N

物化性质

• 熔点：
  125-126 °C
• 沸点：
  486.6±38.0 °C(Predicted)
• 密度：
  1.179±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  N-(3-acetylphenyl)-2-phenylacetamide 、 草酸二乙酯 在 sodium methylate 、 盐酸 作用下， 以 四氢呋喃 、 水 为溶剂， 生成
  参考文献：
  名称：

  Amide-containing diketoacids as HIV-1 integrase inhibitors: Synthesis, structure–activity relationship analysis, and biological activity

  摘要：

  HIV-1 integrase, which catalyzes the integration of the viral genome into the cellular chromosome, is an essential enzyme for retroviral replication, and represents an attractive and validated target in the development of therapeutics against AIDS. In this paper, 17 amide-containing novel diketoacids were designed and synthesized, and their ability to inhibit HIV-1 integrase was tested. The structure-activity relationships were also analyzed. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.077
• 作为产物：
  描述：

  间氨基苯乙酮 、 苯乙酰氯 生成 N-(3-acetylphenyl)-2-phenylacetamide
  参考文献：
  名称：

  Electronic properties of anticonvulsant amides. A C-13 nuclear magnetic resonance study of phenylacetanilides.

  摘要：

  制备了约20种苯胺环上带有对位和间位取代基的苯乙酰苯胺，并测量了它们的C-13核磁共振谱。通过双取代基参数 (DSP) 和 DSP-非线性共振 (DSP-NLR) 方程检查对碳原子的取代基化学位移 (SCS)。通过 DSP 分析获得了极好的相关性。结果表明-NHCOCH2Ph部分是弱电子供体。化学位移数据和推导的相关性与取代的丙酰苯胺获得的数据非常相似。

  DOI：

  10.1248/cpb.31.4172

文献信息

• Structure-based modification of 3-/4-aminoacetophenones giving a profound change of activity on tyrosinase: From potent activators to highly efficient inhibitors
  作者：Ao You、Jie Zhou、Senchuan Song、Guoxun Zhu、Huacan Song、Wei Yi

  DOI：10.1016/j.ejmech.2015.02.013

  日期：2015.3

  In this study, we developed 3-/4-aminoacetophenones and their structure-based 3-/4-aminophenylethylidenethiosemicarbazide derivatives, respectively, as novel tyrosinase activators and inhibitors. Notably, all the obtained thiosemicarbazones displayed more potent tyrosinase inhibitory activities than kojic acid. Especially, compound 7k was found to be the most active tyrosinase inhibitor with IC50 value of 0.291 mu M. The structure-activity relationships (SARs) analysis showed that: (1) the amine group was absolutely necessarily for determining the tyrosinase activation activity; (2) the introduction of thiosemicarbazide group played a very vital role in transforming tyrosinase activators into tyrosinase inhibitors; (3) the phenylethylenethiosemicarbazide moiety was crucial for determining the tyrosinase inhibitory activity; (4) the type of acyl group had no obvious effect on the inhibitory activity; (5) the position of amide substituent on the phenyl ring influenced the tyrosinase inhibitory potency. Moreover, the inhibition mechanism and inhibition kinetics study revealed that compound 7k was reversible and non-competitive inhibitor, and compound 8h was reversible and competitive-uncompetitive mixed-II type inhibitor. (C) 2015 Elsevier Masson SAS. All rights reserved.