4'-methoxymethyl-4,5'-dimethylangelicin | 75663-41-1

• 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'-methoxymethyl-4,5'-dimethylangelicin
• 英文别名: 4'-(methoxymethyl)-4,5'-dimethylangelicin；2H-Furo(2,3-h)-1-benzopyran-2-one, 9-(methoxymethyl)-4,8-dimethyl-；9-(methoxymethyl)-4,8-dimethylfuro[2,3-h]chromen-2-one
• CAS: 75663-41-1
• 化学式: C₁₅H₁₄O₄
• 分子量: 258.274
• InChiKey: WFUCPMJAGVWGNU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  48.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  7-(4-Chlorobut-2-ynoxy)-4-methylchromen-2-one 在 N,N-二乙基苯胺 作用下， 反应 0.5h， 生成 4'-methoxymethyl-4,5'-dimethylangelicin
  参考文献：
  名称：

  微波辅助的克莱森重排。在合成当归霉素衍生物中的应用

  摘要：

  通过4-甲基-7- [4-（羟基，氯，氨基，乙酰氧基和羟基）的克莱森重排，有效并快速地合成了4'-（羟基，氯，氨基，乙酰氧基和甲氧基）-甲基-4,5'-二甲基Angelicins。微波辐射下分别有甲氧基）-丁-2-炔氧基]-香豆素。这种新方法的优点包括操作简便，反应时间短，收率高以及易于使用的后处理程序。

  DOI：

  10.1002/jhet.5570430336

文献信息

• New monofunctional reagents for DNA as possible agents for the photochemotherapy of psoriasis: derivatives of 4,5'-dimethylangelicin
  作者：Francesco Dall'Acqua、Daniela Vedaldi、Sergio Caffieri、Adriano Guiotto、Paolo Rodighiero、Francarosa Baccichetti、Francesco Carlassare、Franco Bordin

  DOI：10.1021/jm00134a010

  日期：1981.2

  With the aim of obtaining new agents for the photochemotherapy of psoriasis, we have prepared monofunctional reagents for DNA by starting from 4,5'-dimethylangelicin (2), an angular furocoumarin, and introducing in a 4'-(hydroxymethyl) (3), 4'-(methoxymethyl) (4), or 4'-(aminomethyl) group (5), in way analogous to what other authors have done previously on trioxsalen, a DNA bifunctional reagent. These new compounds form complexes with DNA in the ground state and by successive irradiation (UV-A) undergo monofunctional photoaddition to the macromolecule. Photobinding to DNA was highest for 3 and gradually lower for 4 and 5, respectively. These compounds do not form interstrand photocross-linkages in DNA and do not show any skin phototoxicity. Fluorimetric studies show that their 4',5' double bond is involved in the photoaddition to DNA. Their photobiological activity evaluated on Ehrlich ascites tumor cells and on T2 phages was strictly connected with their photobinding to DNA. The effect of the introduction of hydroxymethyl and methoxymethyl groups in angular 2 is somewhat similar to that previously described for trioxsalen: the introduction of an aminomethyl group in 2 markedly increases the affinity in the dark for DNA but under UV-A irradiation strongly inhibits photobinding to the macromolecule. By contrast, in the analogous derivative of trioxsalen both the affinity for DNA in the dark and the photobinding to DNA increased.
• Microwave-assisted claisen rearrangement. Application to the synthesis of angelicin derivatives
  作者：Hassan Valizadeh、Abbas Shockravi

  DOI：10.1002/jhet.5570430336

  日期：2006.5

  acetoxy and methoxy)-methyl-4,5′-dimethylangelicins were efficiently and rapidly synthesized via Claisen rearrangement of 4-methyl-7-[4-(hydroxy, chloro, amino, acetoxy and methoxy)-but-2-ynyloxy]-coumarins respectively under microwave irradiation. Prominent among the advantages of this new method are operational simplicity, good yields in short reaction times and easy work-up procedures employed.

  通过4-甲基-7- [4-（羟基，氯，氨基，乙酰氧基和羟基）的克莱森重排，有效并快速地合成了4'-（羟基，氯，氨基，乙酰氧基和甲氧基）-甲基-4,5'-二甲基Angelicins。微波辐射下分别有甲氧基）-丁-2-炔氧基]-香豆素。这种新方法的优点包括操作简便，反应时间短，收率高以及易于使用的后处理程序。