4-[(5-methoxy-1H-indol-3-yl)methyl]-1,3-oxazolidin-2-one | 1070902-26-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 4-[(5-methoxy-1H-indol-3-yl)methyl]-1,3-oxazolidin-2-one
• CAS: 1070902-26-9
• 化学式: C₁₃H₁₄N₂O₃
• 分子量: 246.266
• InChiKey: GSHQCLOTSKKDJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  63.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(二甲氧基甲基)-2,6-二甲氧基苯酚 、 4-[(5-methoxy-1H-indol-3-yl)methyl]-1,3-oxazolidin-2-one 在 三氟乙酸 作用下， 以 四氢呋喃 为溶剂， 以78%的产率得到
  参考文献：
  名称：

  Structure-activity relationship for DNA topoisomerase II-induced DNA cleavage by azatoxin analogues

  摘要：

  Eighteen analogues of the nonintercalative DNA topoisomerase II (topo II)-active epipodophyllotoxin-ellipticine hybrid, azatoxin, were synthesized and evaluated for their ability to induce topo II-mediated DNA strand breaks in vitro. In general, the SAR profile of the azatoxins showed more homology with that of the epipodophyllotoxins than with the ellipticines. Of the compounds studied, only fluoro substitution at the 8-, 9, and 10-positions of azatoxins enhanced activity, with 9-fluoroazatoxin being the most active compound in this series. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00113-2
• 作为产物：
  描述：

  DL-5-甲氧基色氨酸 在 盐酸 、 sodium tetrahydroborate 、 sodium ethanolate 作用下， 以 乙醇 、 水 为溶剂， 反应 11.0h， 生成 4-[(5-methoxy-1H-indol-3-yl)methyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Structure-activity relationship for DNA topoisomerase II-induced DNA cleavage by azatoxin analogues

  摘要：

  Eighteen analogues of the nonintercalative DNA topoisomerase II (topo II)-active epipodophyllotoxin-ellipticine hybrid, azatoxin, were synthesized and evaluated for their ability to induce topo II-mediated DNA strand breaks in vitro. In general, the SAR profile of the azatoxins showed more homology with that of the epipodophyllotoxins than with the ellipticines. Of the compounds studied, only fluoro substitution at the 8-, 9, and 10-positions of azatoxins enhanced activity, with 9-fluoroazatoxin being the most active compound in this series. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00113-2

文献信息

• [EN] 4,5,11,11A-TETRAHYDRO-1H,6H-OXAZOLO[3',4':1,6]PYRIDO[3,4-B]INDOL-3-ONE DERIVATIVES AND THERAPEUTIC USE THEREOF<br/>[FR] DERIVES DE 4,5,11,11A-TETRAHYDRO-1H,6H-OXAZOLO[3',4':1,6]PYRIDO[3,4-B]INDOL-3-ONE ET LEUR UTILISATION EN THERAPEUTIQUE
  申请人：FOURTILLAN

  公开号：WO2008125658A1

  公开（公告）日：2008-10-23

  [EN] The invention relates to a 4,5,11,11a-tetrahydro-1H,6H-oxazolo [3',4' :1,6] pyrido [3,4-b] indol-3-one compound of the general formula (I) in which: R1 is a hydrogen atom or a C₁-C₆ alkoxy group; R2 is a hydrogen atom or a C₁-C₆ alkyl group; R3 is a hydrogen atom, a C₁-C₆ alkyl group, a C₃-C₆ cycloalkyl group, a C₄-C₆ cycloalkene group, a heteroaryl or an aryl group, the aryl group being optionally substituted by one or more groups selected from the C₁-C₆ alkyl, C₁-C₆ alkoxy or cyano groups or by one or more hydrogen atoms; R4 is a hydrogen atom or a C₁-C₆ alkoxy groups, the invention also relates to the mixtures thereof to the pharmaceutically acceptable addition salts thereof, to the isomers, enantiomers, diastereoisomers or mixtures thereof, to a method for preparing the same and to the use thereof in pharmaceutical and/or cosmetic compositions, in particular for adjusting the sleep-wake circadian cycle.
  [FR] La présente invention concerne un composé 4,5,11,11a-tétrahydro-1H,6H-oxazolo [3',4' :1,6] pyrido [3,4-b] indol-3-one de formule générale (I) suivante: formule (I) dans laquelle: R1 représente un atome d'hydrogène ou un groupe alcoxy en C₁-C₆; R2 représente un atome d hydrogène ou un groupe alkyle en C₁-C₆; R3 représente un atome d hydrogène, un groupe alkyle en C₁-C₆, un groupe cycloalkyle en C₃-C₆, un groupe cycloalcène en C₄-C₆, un hétéroaryle ou un groupe aryle, le groupe aryle étant éventuellement substitué par un ou plusieurs groupes choisis parmi les groupes alkyle en C₁-C₆, alcoxy en C₁-C₆, cyano ou par un ou plusieurs atome d'halogène; R4 représente un atome d hydrogène ou un groupe alcoxy en C₁-C₆; ou leurs mélanges, ou leurs sels d'addition pharmaceutiquement acceptables, ou leurs isomères, énantiomères, diastéréoisomères ou leurs mélanges, son procédé de préparation et son utilisation dans des compositions pharmaceutiques et/ou cosmétiques, en particulier pour la régulation du cycle circadien veille-sommeil.