N-Adamantan-1-yl-2,4-dihydroxy-benzamide | 1145869-21-1

• 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-Adamantan-1-yl-2,4-dihydroxy-benzamide
• 英文别名: N-(1-adamantyl)-2,4-dihydroxybenzamide
• CAS: 1145869-21-1
• 化学式: C₁₇H₂₁NO₃
• 分子量: 287.359
• InChiKey: YXZNGGXRXGBQPR-UHFFFAOYSA-N

物化性质

• 沸点：
  544.3±20.0 °C(predicted)
• 密度：
  1.33±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  69.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  4-(((3s,5s,7s)-adamantan-1-yl)carbamoyl)-1,3-phenylene diacetate 在 氢氧化钾 、 水 作用下， 生成 N-Adamantan-1-yl-2,4-dihydroxy-benzamide
  参考文献：
  名称：

  Studies on depigmenting activities of dihydroxyl benzamide derivatives containing adamantane moiety

  摘要：

  Six diphenolic compounds containing adamantane moiety were synthesized and evaluated as potent inhibitors on tyrosinase activity and melanin formation in melan-a cells. The inhibitory activity of 4-adamantyl resorcinol 1 was similar to that of 4-n-butyl resorcinol in both assays. However, dihydroxyl benzamide derivatives 6a-e showed different inhibitory patterns. All derivatives significantly suppressed the cellular melanin formation without tyrosinase inhibitory activities. These behaviors indicated that the introduction of amide bond changes the binding mode of dihydroxyl groups to tyrosinase. Among derivatives, 6d (3,4-dihydroxyl compound) and 6e (2,3-dihydroxyl compound) showed stronger inhibitory activities (IC50 = 1.25 mu M and 0.73 mu M, respectively) as compared to 4-n-butyl resorcinol (IC50 = 21.64 mu M) and hydroquinone (IC50 = 3.97 mu M). This study showed that the position of dihydroxyl substituent at aromatic ring is important for the intercellular inhibition of melanin formation, and also amide linkage and adamantane moiety enhance the inhibition. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.12.106

文献信息

• Studies on depigmenting activities of dihydroxyl benzamide derivatives containing adamantane moiety
  作者：Ho Sik Rho、Heung Soo Baek、Soo Mi Ahn、Jae Won Yoo、Duck Hee Kim、Han Gon Kim

  DOI：10.1016/j.bmcl.2008.12.106

  日期：2009.3

  Six diphenolic compounds containing adamantane moiety were synthesized and evaluated as potent inhibitors on tyrosinase activity and melanin formation in melan-a cells. The inhibitory activity of 4-adamantyl resorcinol 1 was similar to that of 4-n-butyl resorcinol in both assays. However, dihydroxyl benzamide derivatives 6a-e showed different inhibitory patterns. All derivatives significantly suppressed the cellular melanin formation without tyrosinase inhibitory activities. These behaviors indicated that the introduction of amide bond changes the binding mode of dihydroxyl groups to tyrosinase. Among derivatives, 6d (3,4-dihydroxyl compound) and 6e (2,3-dihydroxyl compound) showed stronger inhibitory activities (IC50 = 1.25 mu M and 0.73 mu M, respectively) as compared to 4-n-butyl resorcinol (IC50 = 21.64 mu M) and hydroquinone (IC50 = 3.97 mu M). This study showed that the position of dihydroxyl substituent at aromatic ring is important for the intercellular inhibition of melanin formation, and also amide linkage and adamantane moiety enhance the inhibition. (C) 2008 Elsevier Ltd. All rights reserved.