13-(β-D-glucopyranos-1-yl)-5,7-dihydro-12H-pyrido[3',2':4,5]pyrrolo[2,3-a]furo[3,4-c]carbazole-5,7-dione | 480434-43-3

• 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: 13-(β-D-glucopyranos-1-yl)-5,7-dihydro-12H-pyrido[3',2':4,5]pyrrolo[2,3-a]furo[3,4-c]carbazole-5,7-dione
• 英文别名: 13-(β-D-glucopyranosyl)-12,13-dihydrofuro[3,4-c]pyrido[3',2':4,5]pyrrolo[2,3-a]carbazole-5,7-dione；3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-13-oxa-3,5,23-triazahexacyclo[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: 480434-43-3
• 化学式: C₂₅H₁₉N₃O₈
• 分子量: 489.441
• InChiKey: UEMWUCOCDLDHOC-NBSBONBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  167
• 氢给体数：
  5
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  13-(β-D-glucopyranos-1-yl)-5,7-dihydro-12H-pyrido[3',2':4,5]pyrrolo[2,3-a]furo[3,4-c]carbazole-5,7-dione 在 盐酸羟胺 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以48%的产率得到6-hydroxy-13-(β-D-glucopyranos-1-yl)-5,7-dihydro-12H-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  The synthesis of a family of rebeccamycin analogues in which one indole unit has been replaced by a 7-azaindole moiety is described.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：

  2,5-dihydro-3-(1H-indol-3-yl)-4-[1-(β-D-glucopyranos-1-yl)-pyrrolo[2,3-b]pyridin-3-yl]-furane-2,5-dione 在 碘 作用下， 以 乙腈 为溶剂， 反应 4.0h， 以70%的产率得到13-(β-D-glucopyranos-1-yl)-5,7-dihydro-12H-pyrido[3',2':4,5]pyrrolo[2,3-a]furo[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

• Pyrido-pyrido-pyrrolo pyrrolo-indole and pyrido-pyrrolo pyrrolo carbazole derivatives, method for the production thereof and pharmaceutical compositions containing said derivatives
  申请人：——

  公开号：US20040152721A1

  公开（公告）日：2004-08-05

  Compounds of formula (I): 1 wherein: W 1 and W 2 , together with the carbon atoms to which they are bonded, represent a phenyl group or a pyridyl group, and at least one of the groups W 1 or W 2 represents a pyridyl group, R 1 and R 2 each represent a group of formula U-V as defined in the description, X and X 1 each represent a hydrogen atom or a hydroxy, alkoxy, mercapto or alkylthio group, Y and Y 1 each represent a hydrogen atom, or X and Y, X 1 and Y 1 , together with the carbon atom carrying them, represent a carbonyl or thiocarbonyl group, R 4 and R 5 are as defined in the description, Q 1 , Q 2 represent a hydrogen atom, or Q 1 and Q 2 , together with the carbon atoms carrying them, form an aromatic bond. Medicaments.

  式(I)的化合物：其中：W1和W2与它们连接的碳原子一起表示苯基或吡啶基，且W1或W2中至少一个表示吡啶基，R1和R2分别表示如描述中所定义的U-V式的基团，X和X1分别表示氢原子或羟基、烷氧基、巯基或烷硫基，Y和Y1分别表示氢原子，或X和Y、X1和Y1连同携带它们的碳原子表示羰基或硫代羰基，R4和R5如描述中所定义，Q1、Q2表示氢原子，或Q1和Q2连同携带它们的碳原子形成芳香键。药物。
• US7001906B2
  申请人：——

  公开号：US7001906B2

  公开（公告）日：2006-02-21
• 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.