1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-bromoindoline-2,3-dione | 884496-44-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-bromoindoline-2,3-dione
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(5-bromo-2,3-dioxoindol-1-yl)oxan-2-yl]methyl acetate
• CAS: 884496-44-0
• 化学式: C₂₂H₂₂BrNO₁₁
• 分子量: 556.321
• InChiKey: LAXFKOIQDIEEOC-QKYBYQKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  152
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-bromoindoline-2,3-dione 、 5-碘吲哚-2-酮 在 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 24.0h， 以68%的产率得到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
• 作为产物：
  描述：

  1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-bromoindoline 在 chromium(VI) oxide 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 26.0h， 生成 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-5-bromoindoline-2,3-dione
  参考文献：
  名称：

  Synthesis and antiproliferative activities of diversely substituted glycosyl-isoindigo derivatives

  摘要：

  in the course of structure-activity relationship studies, diversely substituted 1-(beta-(D)-glucopyranosyl)-isoindigo derivatives were prepared from commercially available indolines. Their antiproliferative activities were evaluated toward a panel of human solid cancer cell lines (PC 3, DLD-1, MCF-7, M4Beu, A549, PA 1), a murine cell line (L929) and a human fibroblast primary culture to get an insight into the substitution pattern required for the best biological potencies. (c) 2005 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.10.004

文献信息

• Biological evaluation of glycosyl-isoindigo derivatives against the pathogenic agents of tropical diseases (malaria, Chagas disease, leishmaniasis and human African trypanosomiasis)
  作者：Fadoua Bouchikhi、Fabrice Anizon、Reto Brun、Pascale Moreau

  DOI：10.1016/j.bmcl.2011.08.116

  日期：2011.11

  glycosyl-isoindigo derivatives against the causative agents of tropical diseases (malaria, Chagas disease, leishmaniasis and human African trypanosomiasis) are reported. Some of the compounds tested showed interesting activities with good selectivity indices, particularly against Trypanosoma brucei rhodesiense. These results suggested, for the first time, that glycosyl-isoindigo derivatives could be of interest

  据报道，各种取代的糖基-异靛蓝衍生物对热带病（疟疾，南美锥虫病，利什曼病和人类非洲锥虫病）的病原体具有生物活性。测试的某些化合物表现出令人感兴趣的活性，并具有良好的选择性指数，尤其是对布氏锥虫的抵抗。这些结果首次表明，糖基-异靛蓝衍生物可能对于发现用于治疗热带疾病的新的先导化合物感兴趣。