1-benzyloxymethyl-3-(1-phenylsulfonyl-1H-indol-3-yl)-4-[1-(2-O-tosyl-3,4,6-tri-O-benzyl-β-D-glucopyranos-1-yl)-pyrrolo[2,3-b]pyridin-3-yl]-2,5-dihydro-pyrrole-2,5-dione | 862778-87-8

• 分子结构分类: 有机化合物
• 英文名称: 1-benzyloxymethyl-3-(1-phenylsulfonyl-1H-indol-3-yl)-4-[1-(2-O-tosyl-3,4,6-tri-O-benzyl-β-D-glucopyranos-1-yl)-pyrrolo[2,3-b]pyridin-3-yl]-2,5-dihydro-pyrrole-2,5-dione
• CAS: 862778-87-8
• 化学式: C₆₇H₅₈N₄O₁₂S₂
• 分子量: 1175.35
• InChiKey: ATTRWPSQGQUCBB-AGESRLQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.05
• 重原子数：
  85.0
• 可旋转键数：
  22.0
• 环数：
  12.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  183.79
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  1-benzyloxymethyl-3-(1-phenylsulfonyl-1H-indol-3-yl)-4-[1-(2-O-tosyl-3,4,6-tri-O-benzyl-β-D-glucopyranos-1-yl)-pyrrolo[2,3-b]pyridin-3-yl]-2,5-dihydro-pyrrole-2,5-dione 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以64%的产率得到1-benzyloxymethyl-3-(1H-indol-3-yl)-4-[1-(2-O-tosyl-3,4,6-tri-O-benzyl-β-D-glucopyranos-1-yl)-pyrrolo[2,3-b]pyridin-3-yl]-2,5-dihydro-pyrrole-2,5-dione
  参考文献：
  名称：

  Synthesis of bridged aza-rebeccamycin analogues

  摘要：

  The syntheses of rebeccamycin analogues possessing a 7-azaindole moiety instead of an indole unit, and with both indole and azaindole moieties linked to the carbohydrate are described. In these bridged aza compounds, the oxygen of the pyranose heterocycle is oriented towards either the indole, or the azaindole unit. In these series, compounds bearing a free imide nitrogen were synthesized by coupling the corresponding aglycones with a sugar pre-tosylated in 2-position via a Mitsunobu reaction. To obtain a precursor for bridged aza-rebeccamycin analogues substituted in 6-position on the sugar moiety, a 2,6-ditosylated sugar was used. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.043
• 作为产物：
  描述：

  1-O-acetyl-2-O-tosyl-3,4,6-tri-O-benzyl-D-glucopyranose 在 偶氮二甲酸二异丙酯 、 sodium methylate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 1-benzyloxymethyl-3-(1-phenylsulfonyl-1H-indol-3-yl)-4-[1-(2-O-tosyl-3,4,6-tri-O-benzyl-β-D-glucopyranos-1-yl)-pyrrolo[2,3-b]pyridin-3-yl]-2,5-dihydro-pyrrole-2,5-dione
  参考文献：
  名称：

  Synthesis of bridged aza-rebeccamycin analogues

  摘要：

  The syntheses of rebeccamycin analogues possessing a 7-azaindole moiety instead of an indole unit, and with both indole and azaindole moieties linked to the carbohydrate are described. In these bridged aza compounds, the oxygen of the pyranose heterocycle is oriented towards either the indole, or the azaindole unit. In these series, compounds bearing a free imide nitrogen were synthesized by coupling the corresponding aglycones with a sugar pre-tosylated in 2-position via a Mitsunobu reaction. To obtain a precursor for bridged aza-rebeccamycin analogues substituted in 6-position on the sugar moiety, a 2,6-ditosylated sugar was used. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.04.043

文献信息

• Synthesis and biological activities of 7-aza rebeccamycin analogues bearing the sugar moiety on the nitrogen of the pyridine ring
  作者：Samir Messaoudi、Fabrice Anizon、Paul Peixoto、Marie-Hélène David-Cordonnier、Roy M. Golsteyn、Stéphane Léonce、Bruno Pfeiffer、Michelle Prudhomme

  DOI：10.1016/j.bmc.2006.07.013

  日期：2006.11

  The synthesis of a new family of 7-aza-rebeccamycin analogues in which the sugar moiety is attached to the nitrogen of the pyridine ring is described. The capacity of the newly synthesized compounds to bind to DNA and to inhibit topoisomerase I has been evaluated. Their cytotoxicities toward four tumor cell lines, one murine leukemia L1210 and three human tumor cell lines, one prostate carcinoma DU145

  描述了新的7-氮杂-瑞贝卡霉素类似物家族的合成，其中糖部分连接到吡啶环的氮上。已经评估了新合成的化合物结合DNA和抑制拓扑异构酶I的能力。已经确定了它们对四种肿瘤细胞系，一种鼠白血病L1210和三种人肿瘤细胞系，一种前列腺癌DU145，一种结肠癌HT29和一种非小细胞肺癌A549的细胞毒性。已经评估了它们抑制检查点激酶Chk1的能力。