5-[4-(β-D-allopyranosyloxy)benzylidene]-2-thiobarbituric acid | 950768-59-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-[4-(β-D-allopyranosyloxy)benzylidene]-2-thiobarbituric acid
• 英文别名: 2-sulfanylidene-5-[[4-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methylidene]-1,3-diazinane-4,6-dione
• CAS: 950768-59-9
• 化学式: C₁₇H₁₈N₂O₈S
• 分子量: 410.405
• InChiKey: DJJBVOWXRZSNNE-WWRHJZOGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  190
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4,6-二羟基-2-巯基嘧啶 、 豆腐果苷 以 乙醇 为溶剂， 反应 2.0h， 以81%的产率得到5-[4-(β-D-allopyranosyloxy)benzylidene]-2-thiobarbituric 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.