N-(3,5-二甲基苯基)-3-甲基苯甲酰胺 | 346720-25-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(3,5-二甲基苯基)-3-甲基苯甲酰胺
• 中文别名: 3-甲基-N-(3,5-二甲基苯基)苯甲酰胺
• 英文名称: N-(3,5-dimethylphenyl)-3-methylbenzamide
• CAS: 346720-25-0
• 化学式: C₁₆H₁₇NO
• mdl: MFCD01034055
• 分子量: 239.317
• InChiKey: KLZZKRUWHXMCFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  29.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-氨基-3,5-二甲苯 、 间甲基苯甲酰氯 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以93%的产率得到N-(3,5-二甲基苯基)-3-甲基苯甲酰胺
  参考文献：
  名称：

  Identification of a potent and noncytotoxic inhibitor of melanin production

  摘要：

  On the basis of a hit from random screening, biaryl amide derivatives were prepared in a combinatorial manner via parallel solution-phase synthesis, and their effects on melanocytes were investigated to discover new effective skin depigmenting agents. Among the 120 derivatives prepared, five members exhibited a >30% reduction of melanin production at 30 mu M with a cell viability of >90%. In particular, compound A(3)/B-5 exhibited effective inhibitory activity on melanin synthesis. Although the inhibition percentage of A(3)/B-5 was slightly lower than that of the positive reference compound, phenylthiourea (PTU), A(3)/B-5 demonstrated a much better cell viability than PTU. In vivo evaluation of A(3)/B-5 also showed a significant decrease of melanin pigments. In addition, the in silico classification model was built based on the experimental data of library members. Our results suggest that these biaryl amide derivatives may act as potent skin depigmenting agents. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.034

文献信息

• Identification of a potent and noncytotoxic inhibitor of melanin production
  作者：Soonho Hwang、Sang Yoon Choi、Jin Hee Lee、Shinae Kim、Jinkyung In、Sang Keun Ha、Eunjung Lee、Tae-Yoon Kim、Sun Yeou Kim、Sun Choi、Sanghee Kim

  DOI：10.1016/j.bmc.2010.06.034

  日期：2010.8

  On the basis of a hit from random screening, biaryl amide derivatives were prepared in a combinatorial manner via parallel solution-phase synthesis, and their effects on melanocytes were investigated to discover new effective skin depigmenting agents. Among the 120 derivatives prepared, five members exhibited a >30% reduction of melanin production at 30 mu M with a cell viability of >90%. In particular, compound A(3)/B-5 exhibited effective inhibitory activity on melanin synthesis. Although the inhibition percentage of A(3)/B-5 was slightly lower than that of the positive reference compound, phenylthiourea (PTU), A(3)/B-5 demonstrated a much better cell viability than PTU. In vivo evaluation of A(3)/B-5 also showed a significant decrease of melanin pigments. In addition, the in silico classification model was built based on the experimental data of library members. Our results suggest that these biaryl amide derivatives may act as potent skin depigmenting agents. (C) 2010 Elsevier Ltd. All rights reserved.