5-[4-((2,3,4,6-tetra-O-acetyl)-β-D-allopyranosyloxy)benzylidene]-barbituric acid | 1186032-08-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-[4-((2,3,4,6-tetra-O-acetyl)-β-D-allopyranosyloxy)benzylidene]-barbituric acid
• 英文别名: [(2R,3R,4R,5R,6S)-3,4,5-triacetyloxy-6-[4-[(2,4,6-trioxo-1,3-diazinan-5-ylidene)methyl]phenoxy]oxan-2-yl]methyl acetate
• CAS: 1186032-08-5
• 化学式: C₂₅H₂₆N₂O₁₃
• 分子量: 562.487
• InChiKey: OUIKYOJILBXVGO-UNNUSUAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  40
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  199
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  巴比妥酸 、 4-formylphenyl 2,3,4,6-tetra-O-acetyl-β-D-allopyranoside 以 乙醇 为溶剂， 反应 2.0h， 以90%的产率得到5-[4-((2,3,4,6-tetra-O-acetyl)-β-D-allopyranosyloxy)benzylidene]-barbituric acid
  参考文献：
  名称：

  Synthesis and evaluation of 5-benzylidene(thio)barbiturate-β-d-glycosides as mushroom tyrosinase inhibitors

  摘要：

  A series of 5-benzylidene(thio)barbiturate-beta-D-glycosides were designed, synthesized and evaluated as a new class of mushroom tyrosinase inhibitors. The results demonstrated that most of compounds had more potent inhibitory activities than arbutin (IC50 8.4 mmol/L). Compound 12b was found to be the most potent inhibitor with IC50 value of 0.05 mmol/L. SARs analysis suggested that (1) 5-benzylidenethiobarbiturate substructures were efficacious for the inhibitory activity; (2) the lipophilic property of acetylated sugar moiety facilitated the inhibitory potency; (3) the hydroxyl group of 3'-configuration contributed to the increase of inhibitory effects. In addition, the inhibition mechanism study revealed that 5-benzylidene(thio)barbiturate-beta-D-glycosides were irreversible inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.06.018

文献信息

• Synthesis and evaluation of 5-benzylidene(thio)barbiturate-β-d-glycosides as mushroom tyrosinase inhibitors
  作者：Qin Yan、Rihui Cao、Wei Yi、Liang Yu、Zhiyong Chen、Lin Ma、Huacan Song

  DOI：10.1016/j.bmcl.2009.06.018

  日期：2009.8

  A series of 5-benzylidene(thio)barbiturate-beta-D-glycosides were designed, synthesized and evaluated as a new class of mushroom tyrosinase inhibitors. The results demonstrated that most of compounds had more potent inhibitory activities than arbutin (IC50 8.4 mmol/L). Compound 12b was found to be the most potent inhibitor with IC50 value of 0.05 mmol/L. SARs analysis suggested that (1) 5-benzylidenethiobarbiturate substructures were efficacious for the inhibitory activity; (2) the lipophilic property of acetylated sugar moiety facilitated the inhibitory potency; (3) the hydroxyl group of 3'-configuration contributed to the increase of inhibitory effects. In addition, the inhibition mechanism study revealed that 5-benzylidene(thio)barbiturate-beta-D-glycosides were irreversible inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.