1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)indoline-2,3-dione | 716379-95-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)indoline-2,3-dione
• 英文别名: 1-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]indole-2,3-dione
• CAS: 716379-95-2
• 化学式: C₄₂H₃₉NO₇
• 分子量: 669.774
• InChiKey: IIUMUSHWQIFZKE-BGNMOYDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  50
• 可旋转键数：
  14
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  83.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)indoline-2,3-dione 在 正丁基锂 、 三氯化铝 、 N,N-二甲基苯胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 为溶剂， 反应 23.0h， 生成 3-benzylidene-1-(β-D-glucopyranosyl)indolin-2-one
  参考文献：
  名称：

  Synthesis and biological evaluation of oxindoles and benzimidazolinones derivatives

  摘要：

  The synthesis of new oxindoles and benzimidazolinones derivatives bearing a sugar residue on the aromatic nitrogen is described. The presence of the glycoside moiety should enhance the solubility of these heterocyclic compounds and/or improve the interaction with the active site of the biological targets. The inhibitory activities of these new compounds toward five kinases were examined: KDR (VEGFR-2), FGFR-1, PDGFR-beta, EGFR and Tie 2. Furthermore, the antibacterial activities of the prepared compounds were tested against two Gram-positive bacteria Bacillus cereus and Streptomyces chartreusis, a Gram-negative bacterium Escherichia coli and a yeast Candida albicans. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.01.001
• 作为产物：
  描述：

  1-(β-D-glucopyranosyl)indoline 在 chromium(VI) oxide 、 四丁基碘化铵 、 sodium hydride 、 溶剂黄146 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 丙酮 为溶剂， 反应 20.0h， 生成 1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)indoline-2,3-dione
  参考文献：
  名称：

  Synthesis and biological evaluation of oxindoles and benzimidazolinones derivatives

  摘要：

  The synthesis of new oxindoles and benzimidazolinones derivatives bearing a sugar residue on the aromatic nitrogen is described. The presence of the glycoside moiety should enhance the solubility of these heterocyclic compounds and/or improve the interaction with the active site of the biological targets. The inhibitory activities of these new compounds toward five kinases were examined: KDR (VEGFR-2), FGFR-1, PDGFR-beta, EGFR and Tie 2. Furthermore, the antibacterial activities of the prepared compounds were tested against two Gram-positive bacteria Bacillus cereus and Streptomyces chartreusis, a Gram-negative bacterium Escherichia coli and a yeast Candida albicans. (C) 2004 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2004.01.001

文献信息

• Synthesis of glycosyl-isoindigo derivatives
  作者：Mathieu Sassatelli、Elias Saab、Fabrice Anizon、Michelle Prudhomme、Pascale Moreau

  DOI：10.1016/j.tetlet.2004.04.167

  日期：2004.6

  The synthesis 1-(beta-D-glucopyranosyl)-isoindigo from commercially available indoline is described. The synthetic pathway used allowed the substitution of the aromatic moiety by either electron donor or acceptor substituents. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis and antiproliferative activities of diversely substituted glycosyl-isoindigo derivatives
  作者：M SASSATELLI、F BOUCHIKHI、S MESSAOUDI、F ANIZON、E DEBITON、C BARTHOMEUF、M PRUDHOMME、P MOREAU

  DOI：10.1016/j.ejmech.2005.10.004

  日期：2006.1

  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.
• Synthesis and biological evaluation of oxindoles and benzimidazolinones derivatives
  作者：Samir Messaoudi、Martine Sancelme、Valérie Polard-Housset、Bettina Aboab、Pascale Moreau、Michelle Prudhomme

  DOI：10.1016/j.ejmech.2004.01.001

  日期：2004.5

  The synthesis of new oxindoles and benzimidazolinones derivatives bearing a sugar residue on the aromatic nitrogen is described. The presence of the glycoside moiety should enhance the solubility of these heterocyclic compounds and/or improve the interaction with the active site of the biological targets. The inhibitory activities of these new compounds toward five kinases were examined: KDR (VEGFR-2), FGFR-1, PDGFR-beta, EGFR and Tie 2. Furthermore, the antibacterial activities of the prepared compounds were tested against two Gram-positive bacteria Bacillus cereus and Streptomyces chartreusis, a Gram-negative bacterium Escherichia coli and a yeast Candida albicans. (C) 2004 Elsevier SAS. All rights reserved.