7'-aza-5-bromo-5'-iodo-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)isoindigo | 1160112-80-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 7'-aza-5-bromo-5'-iodo-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)isoindigo
• CAS: 1160112-80-0
• 化学式: C₂₉H₂₅BrIN₃O₁₁
• 分子量: 798.34
• InChiKey: DLPWSUSCNHQVOE-RMOVSUMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.74
• 重原子数：
  45.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  176.73
• 氢给体数：
  1.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  7'-aza-5-bromo-5'-iodo-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)isoindigo 、 2-丙炔-1-基氨基甲酸苄酯 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 6.0h， 以45%的产率得到7'-aza-5'-(N-benzyloxycarbonyl-3-aminoprop-1-ynyl)-5-bromo-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)isoindigo
  参考文献：
  名称：

  Synthesis, kinase inhibitory potencies and in vitro antiproliferative activity of isoindigo and 7′-azaisoindigo derivatives substituted by Sonogashira cross-coupling

  摘要：

  In the course of structure-activity relationship studies we were interested in the synthesis of isoindigo and 7'-azaisoindigo derivatives substituted at the N-1 position by a 1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl), at the 5'-position by various chains introduced by Sonogashira cross-coupling and substituted or not at the 5-position by a bromine atom. To get an insight into the substitution pattern required for the best biological potencies, their kinase inhibitory potencies and their in vitro anti-proliferative activities were evaluated. The derivatives were tested toward four protein kinases (CDK5/p25, GSK3, CK1, Dyrk1A) and their in vitro anti proliferative activity was tested against two human myeloid leukaemia cell lines (K562 and HL60). (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.01.027
• 作为产物：
  描述：

  1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-bromoindoline-2,3-dione 、 2H-吡咯并[2,3-b]吡啶-2-酮,1,3-二氢-5-碘- 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以74%的产率得到7'-aza-5-bromo-5'-iodo-1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)isoindigo
  参考文献：
  名称：

  Synthesis, kinase inhibitory potencies and in vitro antiproliferative activity of isoindigo and 7′-azaisoindigo derivatives substituted by Sonogashira cross-coupling

  摘要：

  In the course of structure-activity relationship studies we were interested in the synthesis of isoindigo and 7'-azaisoindigo derivatives substituted at the N-1 position by a 1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl), at the 5'-position by various chains introduced by Sonogashira cross-coupling and substituted or not at the 5-position by a bromine atom. To get an insight into the substitution pattern required for the best biological potencies, their kinase inhibitory potencies and their in vitro anti-proliferative activities were evaluated. The derivatives were tested toward four protein kinases (CDK5/p25, GSK3, CK1, Dyrk1A) and their in vitro anti proliferative activity was tested against two human myeloid leukaemia cell lines (K562 and HL60). (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.01.027