5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-methoxy-4H-chromen-4-one | 1612925-22-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: 5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-methoxy-4H-chromen-4-one
• 英文别名: 5,7,3',4'-tetra-O-benzyl-3-O-methylquercetin
• CAS: 1612925-22-0
• 化学式: C₄₄H₃₆O₇
• 分子量: 676.766
• InChiKey: SUXIZGFJRNNOGI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.78
• 重原子数：
  51.0
• 可旋转键数：
  14.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  76.36
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-methoxy-4H-chromen-4-one 在 盐酸 、 5%-palladium/activated carbon 、 氢气 、 锌 作用下， 以 甲醇 、 二氯甲烷 为溶剂， -40.0~20.0 ℃ 、101.33 kPa 条件下， 反应 24.5h， 生成
  参考文献：
  名称：

  The First Synthesis of 3-O-Methylcyanidin and the Effect of 3-O-Substitution on Stability Under Acidic Conditions

  摘要：

  The simplest and most common anthocyanin in nature is 3-O-glucosylcyanidin (1), and 3-O-glucosylation is believed to stabilize the chromophore. To clarify the effect of the glucose residue we compared the stability of 1 with its aglycone, cyanidin (2), and newly synthesized 3-O-methylcyanidin (3). In an aqueous solution at pH 1, 1 and 3 showed similar stabilities, and 2 was less stable than 1 and 3, indicating that 3-O-substituion does enhance stability. We also analyzed the co-pigmentation effect of flavocommelin (4) and rutin (5), on the color and stability of 3-O-substituted cyanidins and cyanidin. The bathochromic shift of lambda vismax and stability of the color by addition of 4 was greater than that of rutin (5). 4 might stack closer and stronger to the anthocyanidin chromophore than 5.

  DOI：

  10.3987/com-18-s(t)74
• 作为产物：
  描述：

  溴甲苯 在 盐酸 、 potassium carbonate 作用下， 以 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.0h， 生成 5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-3-methoxy-4H-chromen-4-one
  参考文献：
  名称：

  天然和合成类黄酮作为有效的结核分枝杆菌UGM抑制剂

  摘要：

  这项研究报告了一类新型的尿苷5'-二磷酸（UDP）吡喃半乳糖突变酶（UGM）抑制剂，这些抑制剂是从天然产物中筛选出来的。该酶是参与结核分枝杆菌细胞壁生物合成的重要生物催化剂。类黄酮是UGM的有效抑制剂。新型甲基化类黄酮的合成可以进行结构-活性关系分析，并且可以确定UGM抑制所需的官能团和结构元素。发现最好的抑制剂之一的结合模式是非竞争性的。对接模拟表明，该分子可能以开放构象结合UGM，位于最近被鉴定为“可吸收”口袋的空腔中。重要的是，两种最佳的抑制剂结核分枝杆菌UGM对整个结核分枝杆菌细胞显示中等活性。这项研究报告了第一种天然产物，可作为UGM的抑制剂。考虑到天然产物在药物化学中的重要性，这些结果为发现新的抗结核药物创造了新的机会。

  DOI：

  10.1002/chem.201701812

文献信息

• Synthesized quercetin derivatives stimulate melanogenesis in B16 melanoma cells by influencing the expression of melanin biosynthesis proteins MITF and p38 MAPK
  作者：Kosei Yamauchi、Tohru Mitsunaga、Mizuho Inagaki、Tohru Suzuki

  DOI：10.1016/j.bmc.2014.04.053

  日期：2014.7

  In order to understand the effect of structure-activity relationships on melanogenesis using B16 melanoma cells, 19 quercetin derivatives were synthesized. Among the synthesized compounds, 3-O-methylquercetin (11) and 3',4',7-O-trimethylquercetin (14) increased melanin content more potently than the positive control theophylline, while exhibiting low cytotoxicity. Compound 11 exhibited less melanogenesis-stimulating activity than compound 14. However, 11 increased the expression of tyrosinase and tyrosinase-related protein 1 (TRP-1) to a greater extent than 14, thereby suggesting that melanogenesis in melanoma cells does not depend solely on the expression of the enzymes catalyzing melanin biosynthesis. Furthermore, 14 also stimulated the expression of the microphthalmia-associated transcription factor (MITF) and p-p38 mitogen activated protein kinase (MAPK), while they were not increased by 11. These results suggest that 11 may enhance the expression of tyrosinase and TRP-1 by regulating the proteasomal degradation of melanogenic enzymes and/or by activating other transcriptional factors regulating enzyme expression. (C) 2014 Elsevier Ltd. All rights reserved.