6-methyl-12-(6-chloro-6-deoxy-β-D-glucopyranos-1-yl)-5,7-dihydro-13H-pyrido[3',2':4,5]pyrrolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione | 870153-10-9

• 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: 6-methyl-12-(6-chloro-6-deoxy-β-D-glucopyranos-1-yl)-5,7-dihydro-13H-pyrido[3',2':4,5]pyrrolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione
• 英文别名: 23-[(2R,3R,4S,5S,6S)-6-(chloromethyl)-3,4,5-trihydroxyoxan-2-yl]-13-methyl-3,5,13,23-tetrazahexacyclo[14.7.0.02,10.04,9.011,15.017,22]tricosa-1,4(9),5,7,10,15,17,19,21-nonaene-12,14-dione
• CAS: 870153-10-9
• 化学式: C₂₆H₂₁ClN₄O₆
• 分子量: 520.929
• InChiKey: WQNKKKLGBRJMTI-BLIHKQMBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  37
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  141
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-methyl-12-(6-chloro-6-deoxy-β-D-glucopyranos-1-yl)-5,7-dihydro-13H-pyrido[3',2':4,5]pyrrolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 以72%的产率得到6-methyl-12-(6-azido-6-deoxy-β-D-glucopyranos-1-yl)-5,7-dihydro-13H-pyrido[3',2':4,5]pyrrolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione
  参考文献：
  名称：

  Synthesis and cytotoxicities of 7-aza rebeccamycin analogues bearing various substituents on the sugar moiety, on the imide nitrogen and on the carbazole framework

  摘要：

  The synthesis of a family of rebeccamycin analogues in which one indole unit has been replaced by a 7-azaindole moiety is described. Substitutions have been carried out on the imide nitrogen, on the carbazole framework and on the sugar part. Compounds with a lactam upper heterocycle have also been prepared. The cytotoxicities of the newly synthesized compounds toward four tumor cell lines, one murine leukemia (L1210) and three human tumor cell lines (prostate carcinoma DU145, colon carcinoma HT29, and non-small cell lung carcinoma A549) have been evaluated and compared to those of rebeccamycin and parent non-aza and aza compounds. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.04.002
• 作为产物：
  描述：

  12-(β-D-glucopyranosyl)-6-methyl-12,13-dihydro-5H-pyrido[3',2':4,5]pyrrolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7(6H)-dione 在 吡啶 、 四氯化碳 、 三苯基膦 作用下， 反应 24.0h， 以24%的产率得到6-methyl-12-(3,6-dichloro-3,6-dideoxy-β-D-allopyranos-1-yl)-5,7-dihydro-13H-pyrido[3',2':4,5]pyrrolo[2,3-a]pyrrolo[3,4-c]carbazole-5,7-dione
  参考文献：
  名称：

  Synthesis and cytotoxicities of 7-aza rebeccamycin analogues bearing various substituents on the sugar moiety, on the imide nitrogen and on the carbazole framework

  摘要：

  The synthesis of a family of rebeccamycin analogues in which one indole unit has been replaced by a 7-azaindole moiety is described. Substitutions have been carried out on the imide nitrogen, on the carbazole framework and on the sugar part. Compounds with a lactam upper heterocycle have also been prepared. The cytotoxicities of the newly synthesized compounds toward four tumor cell lines, one murine leukemia (L1210) and three human tumor cell lines (prostate carcinoma DU145, colon carcinoma HT29, and non-small cell lung carcinoma A549) have been evaluated and compared to those of rebeccamycin and parent non-aza and aza compounds. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.04.002

文献信息

• Synthesis and cytotoxicities of 7-aza rebeccamycin analogues bearing various substituents on the sugar moiety, on the imide nitrogen and on the carbazole framework
  作者：Samir Messaoudi、Fabrice Anizon、Stéphane Léonce、Alain Pierré、Bruno Pfeiffer、Michelle Prudhomme

  DOI：10.1016/j.ejmech.2005.04.002

  日期：2005.10

  The synthesis of a family of rebeccamycin analogues in which one indole unit has been replaced by a 7-azaindole moiety is described. Substitutions have been carried out on the imide nitrogen, on the carbazole framework and on the sugar part. Compounds with a lactam upper heterocycle have also been prepared. The cytotoxicities of the newly synthesized compounds toward four tumor cell lines, one murine leukemia (L1210) and three human tumor cell lines (prostate carcinoma DU145, colon carcinoma HT29, and non-small cell lung carcinoma A549) have been evaluated and compared to those of rebeccamycin and parent non-aza and aza compounds. (c) 2005 Elsevier SAS. All rights reserved.