5-(naphthalen-1-ylmethyl)-3-(piperazin-1-ylmethyl)-1,3,4-oxadiazole-2(3H)-thione | 1236055-16-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 5-(naphthalen-1-ylmethyl)-3-(piperazin-1-ylmethyl)-1,3,4-oxadiazole-2(3H)-thione
• 英文别名: 5-(naphthalen-1-ylmethyl)-3-(piperazin-1-ylmethyl)-1,3,4-oxadiazole-2-thione
• CAS: 1236055-16-5
• 化学式: C₁₈H₂₀N₄OS
• 分子量: 340.449
• InChiKey: LDQJRNCCBMXWSH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  72.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  哌嗪 、 聚合甲醛 、 5-(naphthalen-1-ylmethyl)-3H-1,3,4-oxadiazole-2-thione 以 1,4-二氧六环 、 乙醇 为溶剂， 以68%的产率得到5-(naphthalen-1-ylmethyl)-3-(piperazin-1-ylmethyl)-1,3,4-oxadiazole-2(3H)-thione
  参考文献：
  名称：

  Synthesis and biological activity of oxadiazole and triazolothiadiazole derivatives as tyrosinase inhibitors

  摘要：

  A series of 16 oxadiazole and triazolothiadiazole derivatives were designed, synthesized and evaluated as mushroom tyrosinase inhibitors. Five derivatives were found to display high inhibition on the tyrosinase activity ranging from 0.87 to 1.49 mu M. Compound 5 exhibited highest tyrosinase inhibitory activity with an IC50 value of 0.87 +/- 0.16 mu M. The in silico protein-ligand docking using AUTODOCK 4.1 was successfully performed on compound 5 with significant binding energy value of -5.58 kcal/mol. The docking results also showed that the tyrosinase inhibition might be due to the metal chelating effect by the presence of thione functionality in compounds 1-5. Further studies revealed that the presence of hydrophobic group such as cycloamine derivatives played a major role in the inhibition. Piperazine moiety in compound 5 appeared to be involved in an extensive hydrophobic contact and a 2.9 angstrom hydrogen bonding with residue Glu 182 in the active site. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.04.067

文献信息

• Synthesis and biological activity of oxadiazole and triazolothiadiazole derivatives as tyrosinase inhibitors
  作者：Kok Wai Lam、Ahmad Syahida、Zaheer Ul-Haq、Mohd. Basyaruddin Abdul Rahman、Nordin H. Lajis

  DOI：10.1016/j.bmcl.2010.04.067

  日期：2010.6

  A series of 16 oxadiazole and triazolothiadiazole derivatives were designed, synthesized and evaluated as mushroom tyrosinase inhibitors. Five derivatives were found to display high inhibition on the tyrosinase activity ranging from 0.87 to 1.49 mu M. Compound 5 exhibited highest tyrosinase inhibitory activity with an IC50 value of 0.87 +/- 0.16 mu M. The in silico protein-ligand docking using AUTODOCK 4.1 was successfully performed on compound 5 with significant binding energy value of -5.58 kcal/mol. The docking results also showed that the tyrosinase inhibition might be due to the metal chelating effect by the presence of thione functionality in compounds 1-5. Further studies revealed that the presence of hydrophobic group such as cycloamine derivatives played a major role in the inhibition. Piperazine moiety in compound 5 appeared to be involved in an extensive hydrophobic contact and a 2.9 angstrom hydrogen bonding with residue Glu 182 in the active site. (C) 2010 Elsevier Ltd. All rights reserved.