4,4'-dimethylxanthotoxol | 1228691-37-9

• 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'-dimethylxanthotoxol
• 英文别名: 4,9-dimethyl-8-hydroxylpsoralen；9-Hydroxy-3,5-dimethylfuro[3,2-g]chromen-7-one
• CAS: 1228691-37-9
• 化学式: C₁₃H₁₀O₄
• 分子量: 230.22
• InChiKey: YBSOPKOLTBENOH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  59.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,4'-dimethylxanthotoxol 在 甲醇 、 四丁基溴化铵 、 sodium methylate 、 sodium hydroxide 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 11.0h， 生成 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：

  4,4'-dimethylpsoralen 在 [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂ 、 [双(三氟乙酰氧基)碘]苯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 以59%的产率得到4,4'-dimethylxanthotoxol
  参考文献：
  名称：

  Improved synthesis, X-ray structure, and antifungal activity of a sugar-psoralen conjugate: 4,4′-Dimethylxanthotoxol 2,3,4,6-tetra-O-Acetyl-β-D-glucoside

  摘要：

  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].

  DOI：

  10.1080/07328303.2019.1609018

文献信息

• Psoralenquinones as a Novel Class of Proteasome Inhibitors: Design, Synthesis and Biological Evaluation
  作者：Giovanni Marzaro、Valentina Gandin、Christine Marzano、Adriano Guiotto、Adriana Chilin

  DOI：10.1002/cmdc.201100041

  日期：2011.6.6

  Proteasome subunit specificity: Psoralenquinones were identified as a novel class of nonpeptide proteasome inhibitors. Depending on the scaffold decoration, these compounds demonstrate interesting subunit specificity. Interactions with Thr1, Thr21 and Ser129 are critical for inhibition.

  蛋白酶体亚基特异性：补骨脂醌被鉴定为一类新的非肽蛋白酶体抑制剂。取决于脚手架装饰，这些化合物表现出令人感兴趣的亚基特异性。与Thr1，Thr21和Ser129的相互作用对于抑制至关重要。
• Synthesis of methyl-substituted xanthotoxol to clarify prooxidant effect of methyl on radical-induced oxidation of DNA
  作者：Chuan Xiao、Zhi-Guang Song、Zai-Qun Liu

  DOI：10.1016/j.ejmech.2010.02.044

  日期：2010.6

  4-Methyl-8-hydroxylpsoralen (MXan) and 4,9-dimethy1-8-hydroxylpsoralen (DMXan) were synthesized in order to clarify the effect of methyl on the antioxidant effectiveness of xanthotoxol (8-hydroxyl-psoralen, Xan), which were assessed by bleaching beta-carotene in linoleic acid-Triton emulsion, by interacting with 2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate) cationic radical (ABTS(+))center dot, 2,2'-dipheny1-1-picrylhydrazyl radical (DPPH), and galvinoxyl radical, and by protecting DNA against the oxidation induced by Cu(2+)/glutathione (GSH) and 2,2'-azobis(2-amidinopropane hydrochloride) (AAPH). Methyl attaching to xanthotoxol did not affect its ability to protect linoleic acid against autoxidation and to inhibit Cu(2+)/GSH-induced oxidation DNA, but decreased its ability to scavenge ABTS(+)center dot and DPPH, and to protect DNA against AAPH-induced oxidation. Therefore, methyl attenuated the antioxidant effectiveness of xanthotoxol in radical-induced oxidation of DNA.
• 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].
• Synthesis and biological evaluation of glycosylated psoralen derivatives
  作者：Chao-Yue Chen、Jian-Guo Sun、Fei-Yan Liu、Kwok-Pui Fung、Ping Wu、Zhi-Zhen Huang

  DOI：10.1016/j.tet.2012.01.090

  日期：2012.3

  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.