4,4'-dimethyl-8-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)xanthotoxol | 1365411-29-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 4,4'-dimethyl-8-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)xanthotoxol
• 英文别名: [(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(3,5-dimethyl-7-oxofuro[3,2-g]chromen-9-yl)oxyoxan-2-yl]methyl acetate
• CAS: 1365411-29-5
• 化学式: C₂₇H₂₈O₁₃
• 分子量: 560.512
• InChiKey: PWQQSEUZMIZYNM-YSPTVXTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  163
• 氢给体数：
  0
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  4,4'-dimethyl-8-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)xanthotoxol 在 甲醇 、 sodium methylate 作用下， 反应 3.0h， 以94%的产率得到4,4'-dimethyl-8-O-(β-D-glucopyranosyl)xanthotoxol
  参考文献：
  名称：

  Synthesis and biological evaluation of glycosylated psoralen derivatives

  摘要：

  A novel route for the efficient synthesis of a target psoralen moiety, 4,4'-dimethylxanthotoxol, has been developed, which need only four steps using cheap pyrogallol as a starting material. Subsequently, a range of new glycosylated psoralen derivatives were synthesized in good yields with simple procedures and mild reaction conditions. The experiment of biological activity shows that some of the glycosylated psoralen derivatives have antiproliferative activities against human cancer cell lines. A strong photoinduced antiproliferative effects were found under UVA. All of the glycosylated psoralen derivatives exhibited antioxidant activities against the oxidation of DNA induced by Cu2+/glutathione (GSH). Further experiment also demonstrates that the introduction of sugar moieties in some glycosylated psoralen derivatives can improve their antioxidant activities significantly. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.090
• 作为产物：
  描述：

  7,8-diacetonyloxy-4-methylcoumarin 在 四丁基溴化铵 、 sodium hydroxide 、 magnesium iodide 作用下， 以 二氯甲烷 、 水 、 异丙醇 为溶剂， 反应 20.0h， 生成 4,4'-dimethyl-8-O-(2'',3'',4'',6''-tetra-O-acetyl-β-D-glucopyranosyl)xanthotoxol
  参考文献：
  名称：

  Synthesis and biological evaluation of glycosylated psoralen derivatives

  摘要：

  A novel route for the efficient synthesis of a target psoralen moiety, 4,4'-dimethylxanthotoxol, has been developed, which need only four steps using cheap pyrogallol as a starting material. Subsequently, a range of new glycosylated psoralen derivatives were synthesized in good yields with simple procedures and mild reaction conditions. The experiment of biological activity shows that some of the glycosylated psoralen derivatives have antiproliferative activities against human cancer cell lines. A strong photoinduced antiproliferative effects were found under UVA. All of the glycosylated psoralen derivatives exhibited antioxidant activities against the oxidation of DNA induced by Cu2+/glutathione (GSH). Further experiment also demonstrates that the introduction of sugar moieties in some glycosylated psoralen derivatives can improve their antioxidant activities significantly. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2012.01.090

文献信息

• Improved synthesis, X-ray structure, and antifungal activity of a sugar-psoralen conjugate: 4,4′-Dimethylxanthotoxol 2,3,4,6-tetra-<i>O</i>-Acetyl-<i>β</i>-<i>D</i>-glucoside
  作者：Chao-Yue Chen、Ting-Hai Yang、Chang-Duo Pan、Xin Wang

  DOI：10.1080/07328303.2019.1609018

  日期：2019.3.24

  An improved synthesis for 4,4 '-dimethylxanthotoxol 2,3,4,6-tetra-O-acetyl-beta-D-glucoside (1) starting from resorcinol was developed. Crystallographic analysis of glucoside 1 indicated that the dihedral angles between the mean planes of the tricyclic ring system of adjacent molecules was 54.820(22)degrees probably due to the steric hindrance caused by the bulky O-glucoside moiety, which prevents the molecules from packing via pi center dot center dot center dot pi stacking between the tricyclic cores. The antifungal screening data revealed that glucoside 1 had higher inhibition than its parent compound 4,4 '-dimethylxanthotoxol and azoxystrobin against Rhizoctonia solani, Pyricularia grisea, and Alternaria alternate Japanese pear pathotype, with the inhibitory rates of 75.4, 65.7 and 70.1%, respectively, at the 50 mu g/mL concentration.[GRAPHICS].