(3S,4S,5R,6R)-2-(hydroxymethyl)-6-(1H-indol-1-yl)-tetrahydro-2H-pyran-3,4,5-triol | 5059-37-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3S,4S,5R,6R)-2-(hydroxymethyl)-6-(1H-indol-1-yl)-tetrahydro-2H-pyran-3,4,5-triol
• 英文别名: 1-(β-D-glucopyranosyl)indole；1-β-D-glucopyranosylindole；1--indol；β-N-D-Glucopyranosyl-indol；β-N-D-Glucopyranosylindol；1-beta-D-Glucopyranosyl-1H-indole；(2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-indol-1-yloxane-3,4,5-triol
• CAS: 5059-37-0
• 化学式: C₁₄H₁₇NO₅
• 分子量: 279.293
• InChiKey: HYLACZDFUVNNIQ-RKQHYHRCSA-N

物化性质

• 熔点：
  30 °C
• 沸点：
  563.7±50.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  95.1
• 氢给体数：
  4
• 氢受体数：
  5

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  (3S,4S,5R,6R)-2-(hydroxymethyl)-6-(1H-indol-1-yl)-tetrahydro-2H-pyran-3,4,5-triol 在 chromium(VI) oxide 、 正丁基锂 、 四丁基碘化铵 、 sodium hydride 、 溶剂黄146 作用下， 以 四氢呋喃 、 环己烷 、 水 、 丙酮 为溶剂， 反应 10.0h， 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 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 以47%的产率得到(3S,4S,5R,6R)-2-(hydroxymethyl)-6-(1H-indol-1-yl)-tetrahydro-2H-pyran-3,4,5-triol
  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

• Metabolomic “Dark Matter” Dependent on Peroxisomal β-Oxidation in <i>Caenorhabditis elegans</i>
  作者：Alexander B. Artyukhin、Ying K. Zhang、Allison E. Akagi、Oishika Panda、Paul W. Sternberg、Frank C. Schroeder

  DOI：10.1021/jacs.7b11811

  日期：2018.2.28

  Peroxisomal β-oxidation (pβo) is a highly conserved fat metabolism pathway involved in the biosynthesis of diverse signaling molecules in animals and plants. In Caenorhabditis elegans, pβo is required for the biosynthesis of the ascarosides, signaling molecules that control development, lifespan, and behavior in this model organism. Via comparative mass spectrometric analysis of pβo mutants and wildtype

  过氧化物酶体β-氧化（pβo）是一种高度保守的脂肪代谢途径，参与动植物中多种信号分子的生物合成。在秀丽隐杆线虫中，蛔苷的生物合成需要 pβo，蛔苷是控制模型生物体发育、寿命和行为的信号分子。通过对 pβo 突变体和野生型的比较质谱分析，我们表明秀丽隐杆线虫和卫星模型太平洋对虾中的 pβo 有助于数百种以前未知的代谢物的生命阶段特异性生物合成。代谢组的 pβo 依赖性部分出乎意料地多样化，例如与核苷和神经递质代谢交叉。pβo 缺陷突变体中 pβo 的细胞类型特异性恢复进一步揭示了 pβo 依赖性亚代谢组在组织之间存在差异。这些结果表明，脂肪、核苷和其他主要代谢途径的相互作用可以产生结构多样性，让人想起微生物天然产物生物合成中的组合策略所产生的结构多样性。
• Combinatorial Assembly of Modular Glucosides via Carboxylesterases Regulates <i>C. elegans</i> Starvation Survival
  作者：Chester J. J. Wrobel、Jingfang Yu、Pedro R. Rodrigues、Andreas H. Ludewig、Brian J. Curtis、Sarah M. Cohen、Bennett W. Fox、Michael P. O’Donnell、Paul W. Sternberg、Frank C. Schroeder

  DOI：10.1021/jacs.1c05908

  日期：2021.9.15

  library derived from combinatorial assembly of moieties from amino acid, neurotransmitter, and lipid metabolism in the model organism C. elegans. Combining CRISPR-Cas9 genome editing, comparative metabolomics, and synthesis, we show that the carboxylesterase homologue Cel-CEST-1.2 is responsible for specific 2-O-acylation of diverse glucose scaffolds with a wide variety of building blocks, resulting

  最近发现的模块化葡萄糖苷 ( MOGL ) 形成了一个大型代谢物文库，该文库源自模式生物秀丽隐杆线虫中氨基酸、神经递质和脂质代谢的部分组合组装。结合 CRISPR-Cas9 基因组编辑、比较代谢组学和合成，我们表明羧酸酯酶同源物 Cel-CEST-1.2 负责对具有多种构建块的不同葡萄糖支架进行特异性 2- O-酰化，从而产生超过 150不同的 MOGL。我们进一步表明，这种生物合成作用对于相关线虫物种C. briggsae Cbr-CEST-2 中最接近的 Cel-CEST-1.2 同源物是保守的。Cel-cest-1.2的表达和 MOGL 的生物合成是由C. elegans的饥饿条件强烈诱导的， C. elegans是连接营养和生理机制的主要模型系统之一。Cel-cest-1.2缺失导致成年动物在饥饿条件下过早死亡，从而首次了解 MOGL 的生物学功能。
• Novel compounds
  申请人：Nomura Sumihiro

  公开号：US20050233988A1

  公开（公告）日：2005-10-20

  A compound of the formula: wherein Ring A and Ring B are: (1) Ring A is an optionally substituted unsaturated monocyclic heterocyclic ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring, (2) Ring A is an optionally substituted benzene ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring or an optionally substituted unsaturated fused heterobicyclic ring, or (3) Ring A is an optionally substituted unsaturated fused heterobicyclic ring, and Ring B are independently an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring; X is a carbon atom or a nitrogen atom; Y is —(CH 2 ) n — (n is 1 or 2); a pharmaceutically acceptable salt thereof, or a prodrug thereof.

  一种化合物，其化学式为：其中环A和环B分别为：（1）环A为可选取代的不饱和单环杂环，环B为可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环；（2）环A为可选取代的苯环，环B为可选取代的不饱和单环杂环或可选取代的不饱和融合杂双环；或（3）环A为可选取代的不饱和融合杂双环，环B独立地为可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环；X为碳原子或氮原子；Y为—（CH2）n—（n为1或2）；其药学上可接受的盐或其前药。
• GLUCOPYRANOSIDE COMPOUND
  申请人：NOMURA Sumihiro

  公开号：US20120258913A1

  公开（公告）日：2012-10-11

  A compound of the formula: wherein Ring A and Ring B are: (1) Ring A is an optionally substituted unsaturated monocyclic heterocyclic ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring, (2) Ring A is an optionally substituted benzene ring, and Ring B is an optionally substituted unsaturated monocyclic heterocyclic ring or an optionally substituted unsaturated fused heterobicyclic ring, or (3) Ring A is an optionally substituted unsaturated fused heterobicyclic ring, and Ring B are independently an optionally substituted unsaturated monocyclic heterocyclic ring, an optionally substituted unsaturated fused heterobicyclic ring, or an optionally substituted benzene ring; X is a carbon atom or a nitrogen atom; Y is —(CH 2 ) n — (n is 1 or 2); or a pharmaceutically acceptable salt thereof, or a prodrug thereof.

  一种化合物的公式：其中环A和环B是：(1) 环A是一个可选取代的不饱和单环杂环，环B是一个可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环，(2) 环A是一个可选取代的苯环，环B是一个可选取代的不饱和单环杂环或可选取代的不饱和融合杂双环，或(3) 环A是一个可选取代的不饱和融合杂双环，环B是独立的可选取代的不饱和单环杂环、可选取代的不饱和融合杂双环或可选取代的苯环；X是一个碳原子或氮原子；Y是—(CH2)n—(n为1或2)；或其药学上可接受的盐或前药。
• 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.