1-(2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-glucopyranos-1-yl)-1H-indole | 4196-37-6

• 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-1-deoxy-β-D-glucopyranos-1-yl)-1H-indole
• 英文别名: 1-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)indole；1-[(2R,3R,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]indole
• CAS: 4196-37-6
• 化学式: C₄₂H₄₁NO₅
• 分子量: 639.791
• InChiKey: QEFCXCLDURBCKY-QBLDGPCBSA-N

物化性质

• 熔点：
  101.5-102.5 °C
• 沸点：
  766.8±60.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  48
• 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：
  51.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-glucopyranos-1-yl)-1H-indole 在 chromium(VI) oxide 、 正丁基锂 、 溶剂黄146 作用下， 以 四氢呋喃 、 环己烷 、 水 、 丙酮 为溶剂， 反应 4.0h， 生成 3-benzylidene-1-(2,3,4,6-tetra-O-benzyl-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 四丁基碘化铵 、 sodium hydride 、 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 为溶剂， 反应 29.0h， 生成 1-(2,3,4,6-tetra-O-benzyl-1-deoxy-β-D-glucopyranos-1-yl)-1H-indole
  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

• Synthesis and antiproliferative evaluation of glucosylated pyrazole analogs of K252c
  作者：Bachir Douara、Yannick J. Esvan、Elisabeth Pereira、Francis Giraud、Yulia L. Volodina、Dmitry N. Kaluzhny、Alexander A. Shtil、Fabrice Anizon、Pascale Moreau

  DOI：10.1016/j.tet.2018.01.017

  日期：2018.2

  protein kinase isoforms. To evaluate the impact of the introduction of a sugar moiety on the biological activities of this heterocyclic scaffold, four new glucosylated pyrazole analogs of K252c were synthesized. Their biological evaluation demonstrated that most active compounds 11 and 19 substituted by a β-d-glucosyl moiety at N12 or N13 positions exhibited antiproliferative activities toward HCT116 cells

  星形孢菌素糖苷配基K252c的吡唑类似物最近被描述为三种Pim蛋白激酶同工型的有效抑制剂。为了评估糖部分的引入对该杂环支架的生物学活性的影响，合成了K252c的四个新的葡糖基化的吡唑类似物。他们的生物学评估表明，大多数活性化合物11和19在N12或N13位置被β- d-葡萄糖基部分取代，表现出对HCT116细胞的抗增殖活性。
• 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.