3,9-diformyl-12-(4-O-methyl-β-D-glucopyranosyl)-6,7,12,13-tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione | 515132-14-6

• 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: 3,9-diformyl-12-(4-O-methyl-β-D-glucopyranosyl)-6,7,12,13-tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione
• 英文别名: 3,9-diformyl-12-(4-O-methyl-β-D-glucopyranosyl)-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione；3,9-Diformyl-1 2-(4-O-methyl-beta-D-glucopyranosyl)-12,13-dihydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione；3-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]-12,14-dioxo-3,13,23-triazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17(22),18,20-nonaene-7,19-dicarbaldehyde
• CAS: 515132-14-6
• 化学式: C₂₉H₂₃N₃O₉
• 分子量: 557.516
• InChiKey: QEDCECZJGFQNFQ-LVKSHERESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  41
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  180
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3,9-diformyl-12-(4-O-methyl-β-D-glucopyranosyl)-6,7,12,13-tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione 在 镍 氢气 作用下， 以 甲醇 、 水 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 72.0h， 以21%的产率得到3,9-dihydroxymethyl-12-(4-O-methyl-β-D-glucopyranosyl)-6,7,12,13-tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione
  参考文献：
  名称：

  Novel hydroxyalkyl indolocarbazole derivatives, preparation method and pharmaceutical compositions containing the same

  摘要：

  化合物的结构式（I）如下：其中：R1和R2分别代表从氢、烷基、芳基烷基、羟基、羟基烷基、二羟基烷基、烷氧基、烷氧基烷基、氨基和氨基烷基（可选择取代）中选择的基团，Ra和Rb各自代表一个烷基链，X1、X2和X3分别代表从羟基、烷氧基、芳氧基、芳基烷氧基、烷基、氨基（可选择取代）、卤素、烷基羰氧基和叠氮基中选择的基团，X4代表一个甲基亚甲基基团或一个按照说明中定义的公式—Rc—X1的基团，它们的异构体以及它们与药学上可接受的酸或碱形成的加合盐。

  公开号：

  US20040242508A1
• 作为产物：
  描述：

  5H-indolo(2,3-a)pyrrolo(3,4-c)carbazole-5,7(6h)-dione,1,11-dichloro-12,13-dihydro-12-(4-omethyl-beta-d-glucopyranosyl) 在 吡啶 、 ammonium hydroxide 、 四氯化钛 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 67.5h， 生成 3,9-diformyl-12-(4-O-methyl-β-D-glucopyranosyl)-6,7,12,13-tetrahydro-5H-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione
  参考文献：
  名称：

  Semi-synthesis, topoisomerase I and kinases inhibitory properties, and antiproliferative activities of new rebeccamycin derivatives

  摘要：

  In the course of structure-activity relationship studies, new rebeccamycin derivatives substituted in 3,9-positions on the indolocarbazole framework, and a 2,3-anhydro derivative were prepared by semi-synthesis from rebeccamycin. The antiproliferative activities against nine tumor cell lines were determined and the effect on the cell cycle of murine leukemia L1210 cells was examined. Their DNA binding properties and inhibitory properties toward topoisomerase I and three kinases PKCzeta, CDKI/cyclin B, CDK5/p25 and a phosphatase cdc25A were evaluated. The 3,9-dihydroxy derivative is the most efficient compound of this series toward CDKI/cyclin B and CDK5/p25. It is also characterized as a DNA binding topoisomerase I poison. Its broad spectrum of molecular activities likely accounts for its cytotoxic potential. This compound which displays a tumor cell line-selectivity may represent a new lead for subsequent drug design in this series of glycosylated indolocarbazoles. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.09.014