1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole-3-carbaldehyde | 53838-86-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole-3-carbaldehyde
• 英文别名: [(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(3-formylindol-1-yl)oxan-2-yl]methyl acetate
• CAS: 53838-86-1
• 化学式: C₂₃H₂₅NO₁₀
• 分子量: 475.452
• InChiKey: DQUXHOJZINAEMW-XNBWIAOKSA-N

物化性质

• 熔点：
  203-205 °C(Solv: methanol (67-56-1))
• 沸点：
  595.7±50.0 °C(Predicted)
• 密度：
  1.38±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  136
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole-3-carbaldehyde 在 三乙基硅烷 、 三氟化硼乙醚 、 magnesium 、 1,2-二溴乙烷 作用下， 以 四氢呋喃 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 1.0h， 生成 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(3-(4-ethylbenzyl)-1H-indol-1-yl)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  3取代的N-糖苷吲哚的高效合成，可用作钠依赖性葡萄糖转运蛋白抑制剂

  摘要：

  描述了两种N-糖苷吲哚1和2的实用合成方法，已确定它们是高效的钠依赖性葡萄糖转运蛋白（SGLT）抑制剂。合成过程的重点包括选择性和定量的Vilsmeier酰化反应和高产率的Grignard偶联反应。已开发的化学方法已用于制备两种单独的SGLT抑制剂1和2，无需进行色谱分析即可用于临床评估。

  DOI：

  10.1021/op3001355
• 作为产物：
  描述：

  1-(β-D-glucopyranosyl)indoline 在 吡啶 、 4-二甲氨基吡啶 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三氯氧磷 作用下， 以 1,4-二氧六环 、 氯仿 、 水 、 1,2-二氯乙烷 为溶剂， 生成 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole-3-carbaldehyde
  参考文献：
  名称：

  Novel Indole-N-glucoside, TA-1887 As a Sodium Glucose Cotransporter 2 Inhibitor for Treatment of Type 2 Diabetes

  摘要：

  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.

  DOI：

  10.1021/ml400339b

文献信息

• Synthesis of 1-Glycosyl Derivatives of Benzocamalexin
  作者：Martin Humeník、Milan Dzurilla、Peter Kutschy、Eva Solčániová、Vladimír Kováčik、Slávka Bekešová

  DOI：10.1135/cccc20041657

  日期：——

  The linear synthesis of 1-(β-D-glucopyranosyl)-, 1-(β-D-galactopyranosyl)-, 1-(β-D-mannopyranosyl)- and 1-(β-D-ribofuranosyl)benzocamalexin was elaborated from indoline as a starting compound and corresponding pentaacetylhexoses or 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribose as suitable glycosyl donors.

  线性合成1-(β-D-葡萄糖吡喃基)-、1-(β-D-半乳糖吡喃基)-、1-(β-D-甘露糖吡喃基)-和1-(β-D-核糖呋喃基)苯并卡马来新的方法从吲哚作为起始化合物和相应的五乙酰基己糖或1-O-乙酰-2,3,5-三-O-苯甲酰-D-核糖作为适当的糖基供体进行了阐述。
• A Linear Synthesis of 1-(β-D-Glucopyranosyl)brassinin, -brassenin A, -brassenin B and 9-(β-D-Glucopyranosyl)cyclobrassinin
  作者：Peter Kutschy、Marian Sabol、Renata Marušková、Zuzana Čurillová、Milan Dzurilla、Imrich Géci、Juraj Alföldi、Vladimír Kováčik

  DOI：10.1135/cccc20040850

  日期：——

  The first synthesis of 1-(β-D-glucopyranosyl)brassinin, 1-(β-D-glucopyranosyl)brassenin A, 1-(β-D-glucopyranosyl)brassenin B and 9-(β-D-glucopyranosyl)cyclobrassinin, nucleoside analogs derived from indole phytoalexins, was achieved by linear approach, using the 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indole-3-carbaldehyde as a starting compound. Antiproliferative and antimicrobial activity of synthesized compounds against murine leukaemia tumor cell line L1210 and selected bacteria and fungi was examined and compared with the corresponding phytoalexin aglycons.

  使用线性方法，以1-(2,3,4,6-四<斜体>O-乙酰基-β-D-葡萄糖吡唑素-3-甲醛为起始化合物，首次合成了来自吲哚类植物抗菌素的核苷类似物1-(β-D-葡萄糖吡喃糖基)油菜素、1-(β-D-葡萄糖吡喃糖基)油菜素A、1-(β-D-葡萄糖吡喃糖基)油菜素B和9-(β-D-葡萄糖吡喃糖基)环油菜素。检测并比较了合成化合物与相应植物抗菌素原核苷的抗增殖和抗微生物活性，包括小鼠白血病肿瘤细胞系L1210以及选择的细菌和真菌。
• Synthesis of β-D-Glucopyranosides of 6-Substituted 2-(Indol-3-yl)benzothiazoles
  作者：Martin Humeník、Peter Kutschy、Katarína Valková、Branislav Horváth、Vladimír Kováčik、Slávka Bekešová

  DOI：10.1135/cccc20050072

  日期：——

  A linear synthesis of substituted 1-(β-D-glucopyranosyl)benzocamalexins starting from indoline and penta-O-acetyl-β-D-glucopyranose was elaborated. Jacobson cyclization of corresponding 4-substituted peracetylated β-D-glucopyranosylindole-3-carbothioanilides employing potassium ferricyanide under basic conditions was a key synthetic step.

  从吲哚和五个-O-乙酰基-β-D-葡萄糖吡喃糖起始的取代的1-（β-D-葡萄糖苷）苯并卡马莱辛的线性合成被阐明。使用钾铁氰化物在碱性条件下进行对应的4-取代过乙酰化的β-D-葡萄糖苷吲哚-3-羧硫基苯胺的Jacobson环化反应是关键的合成步骤。
• 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。
• PROCESS FOR THE PREPARATION OF COMPOUNDS USEFUL AS INHIBITORS OF SGLT-2
  申请人：Wells Kenneth M.

  公开号：US20140206858A1

  公开（公告）日：2014-07-24

  The present invention is directed to a novel process for the preparation of compounds having inhibitory activity against sodium-dependent glucose transporter (SGLT) being present in the intestine or kidney.

  本发明涉及一种新型的制备具有抑制肠道或肾脏中存在的钠依赖性葡萄糖转运体（SGLT）活性的化合物的方法。