12,13-[1,2-(6-azido-6-deoxy-4-O-methyl-D-mannopyranosyl)]-6,7,12,13-tetrahydro(5H)-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione | 340162-48-3

• 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: 12,13-[1,2-(6-azido-6-deoxy-4-O-methyl-D-mannopyranosyl)]-6,7,12,13-tetrahydro(5H)-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione
• 英文别名: (2R,4R,5S,6R,7S)-4-(azidomethyl)-6-hydroxy-5-methoxy-3-oxa-1,8,18-triazaoctacyclo[13.12.2.02,7.08,29.09,14.016,20.021,28.022,27]nonacosa-9,11,13,15,20,22,24,26,28-nonaene-17,19-dione
• CAS: 340162-48-3
• 化学式: C₂₇H₂₀N₆O₅
• 分子量: 508.493
• InChiKey: GUIDPPMFTGUIRL-SFSUPHRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  38
• 可旋转键数：
  3
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  12,13-[1,2-(6-azido-6-deoxy-4-O-methyl-D-mannopyranosyl)]-6,7,12,13-tetrahydro(5H)-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione 在 10percent Pd/C 氢气 作用下， 生成 12,13-[1,2-(6-deoxy-6-amino-4-O-methyl-D-mannopyranosyl)]-6,7,12,13-tetrahydro(5H)-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione
  参考文献：
  名称：

  Syntheses and Antiproliferative Activities of New Rebeccamycin Derivatives with the Sugar Unit Linked to Both Indole Nitrogens

  摘要：

  The synthesis of new rebeccamycin derivatives, in which the carbohydrate moiety is attached to both indole nitrogens, is described. The newly synthesized compounds were tested for their abilities to block the cell cycle of murine leukemia L1210 cells and their in vitro antiproliferative activities against four tumor cell lines (murine L1210 leukemia and human HT29 colon carcinoma, A549 non-small-cell lung carcinoma, K-562 leukemia). Their biological activities are compared with those of the parent compound rebeccamycin. Some of the now compounds exhibit potent antiproliferative activities, either against the four cell lines or mostly the two leukemias (L1210 and K-562 cell lines). The 3,9-diformyl analogue 9 was selective toward L1210 cells, whereas the 3,9-dibromo 16 was strongly cytotoxic toward the four cell lines tested. Nonselective compound 16 and 3,9-dinitro 13, which exhibited selectivity toward leukemia tumor cell lines, were selected for in-depth evaluation, including in vivo experiments.

  DOI：

  10.1021/jm011045t
• 作为产物：
  描述：

  (2R,4R,5S,6R,7S)-6-hydroxy-4-(hydroxymethyl)-5-methoxy-3-oxa-1,8,18-triazaoctacyclo[13.12.2.02,7.08,29.09,14.016,20.021,28.022,27]nonacosa-9,11,13,15,20,22,24,26,28-nonaene-17,19-dione 在 吡啶 、 四氯化碳 、 sodium azide 、 三苯基膦 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 51.0h， 生成 12,13-[1,2-(6-azido-6-deoxy-4-O-methyl-D-mannopyranosyl)]-6,7,12,13-tetrahydro(5H)-indolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione
  参考文献：
  名称：

  Syntheses and Antiproliferative Activities of New Rebeccamycin Derivatives with the Sugar Unit Linked to Both Indole Nitrogens

  摘要：

  The synthesis of new rebeccamycin derivatives, in which the carbohydrate moiety is attached to both indole nitrogens, is described. The newly synthesized compounds were tested for their abilities to block the cell cycle of murine leukemia L1210 cells and their in vitro antiproliferative activities against four tumor cell lines (murine L1210 leukemia and human HT29 colon carcinoma, A549 non-small-cell lung carcinoma, K-562 leukemia). Their biological activities are compared with those of the parent compound rebeccamycin. Some of the now compounds exhibit potent antiproliferative activities, either against the four cell lines or mostly the two leukemias (L1210 and K-562 cell lines). The 3,9-diformyl analogue 9 was selective toward L1210 cells, whereas the 3,9-dibromo 16 was strongly cytotoxic toward the four cell lines tested. Nonselective compound 16 and 3,9-dinitro 13, which exhibited selectivity toward leukemia tumor cell lines, were selected for in-depth evaluation, including in vivo experiments.

  DOI：

  10.1021/jm011045t