6-methyl-13-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-4b,12,12b,13-tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione | 1070352-28-1

• 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: 6-methyl-13-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-4b,12,12b,13-tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione
• CAS: 1070352-28-1
• 化学式: C₂₇H₂₅N₃O₇
• 分子量: 503.511
• InChiKey: RSCFQZVJRNOOFT-SRYAQXPCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.38
• 重原子数：
  37.0
• 可旋转键数：
  2.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  146.56
• 氢给体数：
  5.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  6-methyl-13-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-4b,12,12b,13-tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 为溶剂， 以101.2 mg的产率得到6-methyl-12-(β-D-glucopyranosyl)-6,7,12,13-tetrahydroindolo<2,3-a>pyrrolo<3,4-c>carbazole-5,7-dione
  参考文献：
  名称：

  A concise approach to 1,11-didechloro-6-methyl-4′-O-demethyl rebeccamycin and its binding to human serum albumin: Fluorescence spectroscopy and molecular modeling method

  摘要：

  1,11-Didechloro-6-methyl-4'-O-demethyl rebeccamycin (JDC-108), a rebeccamycin analog possessing potent anti-tumor activities, was prepared via a concise one-pot strategy in good yield. The interaction between JDC-108 and human serum albumin (HSA) was studied by spectroscopic methods including fluorescence spectroscopy, UV-vis absorption spectrum, and molecular modeling. The quenching mechanism of fluorescence of HSA by JDC-108 was discussed. The number of binding sites n and apparent binding constant K were measured by fluorescence quenching method. The thermodynamic parameters Delta H, Delta G, Delta S at different temperatures were calculated and the results indicated the binding reaction was mainly entropy-driven and hydrophobic forces played major role in the reaction. The distance r between donor ( HSA) and acceptor (JDC-108) was obtained according to Forster theory of non-radiation energy transfer. Synchronous fluorescence and UV-vis absorption spectrum were used to investigate the molecular conformation of HSA molecules with addition of JDC-108 and the result indicated that molecular conformation of HSA molecules was changed in the presence of JDC-108 and the hydrophobic interaction played a major role in JDC-108-HSA association, which was in good agreement with the results of molecular modeling study. In addition, the effect of common ions on the binding constants of JDC-108-HSA complex was also discussed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.017
• 作为产物：
  描述：

  D-葡萄糖 、 6-methyl-4b,12,12b,13-tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione 在 硫酸氢铵 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 6-methyl-13-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-4b,12,12b,13-tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione
  参考文献：
  名称：

  A concise approach to 1,11-didechloro-6-methyl-4′-O-demethyl rebeccamycin and its binding to human serum albumin: Fluorescence spectroscopy and molecular modeling method

  摘要：

  1,11-Didechloro-6-methyl-4'-O-demethyl rebeccamycin (JDC-108), a rebeccamycin analog possessing potent anti-tumor activities, was prepared via a concise one-pot strategy in good yield. The interaction between JDC-108 and human serum albumin (HSA) was studied by spectroscopic methods including fluorescence spectroscopy, UV-vis absorption spectrum, and molecular modeling. The quenching mechanism of fluorescence of HSA by JDC-108 was discussed. The number of binding sites n and apparent binding constant K were measured by fluorescence quenching method. The thermodynamic parameters Delta H, Delta G, Delta S at different temperatures were calculated and the results indicated the binding reaction was mainly entropy-driven and hydrophobic forces played major role in the reaction. The distance r between donor ( HSA) and acceptor (JDC-108) was obtained according to Forster theory of non-radiation energy transfer. Synchronous fluorescence and UV-vis absorption spectrum were used to investigate the molecular conformation of HSA molecules with addition of JDC-108 and the result indicated that molecular conformation of HSA molecules was changed in the presence of JDC-108 and the hydrophobic interaction played a major role in JDC-108-HSA association, which was in good agreement with the results of molecular modeling study. In addition, the effect of common ions on the binding constants of JDC-108-HSA complex was also discussed. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2008.07.017