1-(β-D-glucopyranosyl)indoline | 39264-64-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(β-D-glucopyranosyl)indoline
• 英文别名: 1--indolin；1-(D-β-Glucopyranosyl)-indolin；(2R,3R,4S,5S,6R)-2-(2,3-dihydroindol-1-yl)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 39264-64-7；39264-63-6；40837-51-2
• 化学式: C₁₄H₁₉NO₅
• 分子量: 281.309
• InChiKey: LDRVOIOWMVOAJP-RKQHYHRCSA-N

物化性质

• 沸点：
  537.7±50.0 °C(Predicted)
• 密度：
  1.478±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  93.4
• 氢给体数：
  4
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  1-(β-D-glucopyranosyl)indoline 在 chromium(VI) oxide 、 正丁基锂 、 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 、 环己烷 、 水 、 丙酮 为溶剂， 反应 22.0h， 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：

  吲哚啉 、 D-葡萄糖 以 乙醇 为溶剂， 生成 1-(β-D-glucopyranosyl)indoline
  参考文献：
  名称：

  萘并[2,1-α]吡咯并[3,4- c ]咔唑-5,7（6 H，12 H）-二酮糖苷的合成，细胞毒活性和细胞周期阻滞特征

  摘要：

  萘并[2,1-α]吡咯并[3,4- c ]咔唑-5,7（6 H，12 H）-二酮（NPCD）是一种非常有效且选择性的细胞周期蛋白D1-CDK4抑制剂，可在乳腺肿瘤细胞系中诱导强烈的G1期阻滞。在这项工作中，介绍了五种NPCD糖苷的合成及其对八种肿瘤细胞系的细胞毒活性，以及​​对它们的细胞周期阻滞特性的研究。结果表明，在NPCD上引入糖部分并不会影响其大部分细胞毒性活性，而糖部分的微妙结构会强烈影响其潜在机制。此外，NPCD在BxPC3前列腺细胞和MCF-7乳腺细胞中显示出不同的细胞周期停滞特征，而NPCD苷在MCF-7和BxPC3细胞中共享相似的细胞周期停滞特征，

  DOI：

  10.1016/j.bmcl.2011.04.145

文献信息

• Sweet (hetero)aromatics: glycosylated templates for the construction of saccharide mimetics
  作者：Christine Wiebe、Claudine Schlemmer、Stefan Weck、Till Opatz

  DOI：10.1039/c1cc13078a

  日期：——

  Mono- and diglycosylated aromatics and heteroaromatics may serve as building blocks for the construction of metabolically stable mimetics of oligosaccharides. Methods for their preparation from monosaccharidic precursors by direct C-glycosylation, dipolar cycloaddition or Larock cyclization are described.

  单糖基和二糖基修饰的芳香化合物和杂芳香化合物可作为构建代谢稳定的低聚糖模拟物的砌块。本文描述了通过直接C-糖基化、偶极环加成或Larock环化反应从单糖前体合成这些化合物的方法。
• Synthesis of 1,3- and 2,3-Diglycosylated Indoles as Potential Trisaccharide Mimetics
  作者：Till Opatz、Christine Wiebe、Silvia Fusté de la Sotilla

  DOI：10.1055/s-0031-1290761

  日期：2012.5

  Diglycosylated heteroaromatics may serve as metabolically stable mimetics of trisaccharides. Herein, the preparation of several 1,3- and 2,3-diglycosylindoles by direct C-glycosylation of monoglycosylated precursors is described.
• 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 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.
• Novel Indole-<i>N</i>-glucoside, TA-1887 As a Sodium Glucose Cotransporter 2 Inhibitor for Treatment of Type 2 Diabetes
  作者：Sumihiro Nomura、Yasuo Yamamoto、Yosuke Matsumura、Kiyomi Ohba、Shigeki Sakamaki、Hirotaka Kimata、Keiko Nakayama、Chiaki Kuriyama、Yasuaki Matsushita、Kiichiro Ueta、Minoru Tsuda-Tsukimoto

  DOI：10.1021/ml400339b

  日期：2014.1.9

  Inhibition of the renal sodium glucose cotransporter (SGLT) increases urinary glucose excretion (UGE) and thus reduces blood glucose levels during hyperglycemia. To explore the potential of new antihyperglycemic agents, we synthesized and determined the human SGLT2 (hSGLT2) inhibitory potential of novel substituted 3-benzylindole-N-glucosides 6. Optimization of 6 resulted in the discovery of 3-(4-cyclopropylbenzyl)-4-fluoroindole-N-glucoside 6a-4 (TA-1887), a highly potent and selective hSGLT2 inhibitor, with pronounced antihyperglycemic effects in high-fat diet-fed KK (HF-KK) mice. Our results suggest the potential of indole-N-glucosides as novel antihyperglycemic agents through inhibition of renal SGLT2.