4-formylphenyl (2,3-O-isopropylidene)-β-D-allopyranoside | 950761-90-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-formylphenyl (2,3-O-isopropylidene)-β-D-allopyranoside
• 英文别名: 4-((3aR,4S,6R,7R,7aR)-7-hydroxy-6-(hydroxymethyl)-2,2-dimethyl-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yloxy)benzaldehyde；4-[[(3aR,4S,6R,7R,7aR)-7-hydroxy-6-(hydroxymethyl)-2,2-dimethyl-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]oxy]benzaldehyde
• CAS: 950761-90-7
• 化学式: C₁₆H₂₀O₇
• 分子量: 324.331
• InChiKey: SZCITRIINKLOPJ-KJWHEZOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  94.4
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-formylphenyl (2,3-O-isopropylidene)-β-D-allopyranoside 在 三乙胺 、 三氯氧磷 作用下， 以 氯仿 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of helicid analogues as mushroom tyrosinase inhibitors

  摘要：

  A series of helicid analogues were synthesized and evaluated as tyrosinase inhibitors. The results demonstrated that some compounds had more potent inhibitory activities than arbutin (IC50 7.3 mM). In particular, compound 1c bearing 4,6-O-benzylidene substituent on the sugar moiety was found to be the most potent inhibitor with IC50 value of 0.052 mM. The inhibition kinetics analyzed by Lineweaver-Burk plots revealed that helicid analogues were competitive inhibitors. The Circular dichroism spectra indicated that those compounds induced conformational changes of mushroom tyrosinase upon binding. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.056
• 作为产物：
  描述：

  豆腐果苷 、 丙酮 在 碘 作用下， 反应 3.0h， 以56%的产率得到4-formylphenyl (2,3-O-isopropylidene)-β-D-allopyranoside
  参考文献：
  名称：

  Synthesis and biological evaluation of helicid analogues as mushroom tyrosinase inhibitors

  摘要：

  A series of helicid analogues were synthesized and evaluated as tyrosinase inhibitors. The results demonstrated that some compounds had more potent inhibitory activities than arbutin (IC50 7.3 mM). In particular, compound 1c bearing 4,6-O-benzylidene substituent on the sugar moiety was found to be the most potent inhibitor with IC50 value of 0.052 mM. The inhibition kinetics analyzed by Lineweaver-Burk plots revealed that helicid analogues were competitive inhibitors. The Circular dichroism spectra indicated that those compounds induced conformational changes of mushroom tyrosinase upon binding. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.10.056

文献信息

• Synthesis and biological evaluation of helicid analogues as mushroom tyrosinase inhibitors
  作者：Wei Yi、Rihui Cao、Huan Wen、Qin Yan、Binhua Zhou、Yiqian Wan、Lin Ma、Huacan Song

  DOI：10.1016/j.bmcl.2008.10.056

  日期：2008.12

  A series of helicid analogues were synthesized and evaluated as tyrosinase inhibitors. The results demonstrated that some compounds had more potent inhibitory activities than arbutin (IC50 7.3 mM). In particular, compound 1c bearing 4,6-O-benzylidene substituent on the sugar moiety was found to be the most potent inhibitor with IC50 value of 0.052 mM. The inhibition kinetics analyzed by Lineweaver-Burk plots revealed that helicid analogues were competitive inhibitors. The Circular dichroism spectra indicated that those compounds induced conformational changes of mushroom tyrosinase upon binding. (C) 2008 Elsevier Ltd. All rights reserved.