1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indoline | 22855-03-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indoline
• 英文别名: 1-(tetra-O-acetyl-β-D-glucopyranosyl)indoline；1--indolin；N-<β-D-Tetraacetylglucopyranosyl>-indolin；1-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-indolin；β-D-Glucopyranosyl-(indolin)-peracetat；Acetic acid 3,4,5-triacetoxy-6-(2,3-2H-indol-1-YL)-4H-pyran-2-ylmethyl ester；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(2,3-dihydroindol-1-yl)oxan-2-yl]methyl acetate
• CAS: 22855-03-4；23477-48-7；38730-31-3；38740-49-7
• 化学式: C₂₂H₂₇NO₉
• 分子量: 449.458
• InChiKey: RTRYJIOTUZUULJ-QMCAAQAGSA-N

物化性质

• 熔点：
  117.8-118.5 °C
• 沸点：
  537.4±50.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  118
• 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)indoline 在 magnesium 、 1,2-二溴乙烷 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三氯氧磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 、 1,2-二氯乙烷 为溶剂， 生成
  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
• 作为产物：
  描述：

  D-葡萄糖 在 吡啶 作用下， 以 乙醇 、 水 为溶剂， 反应 42.0h， 生成 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)indoline
  参考文献：
  名称：

  Sweet (hetero)aromatics: glycosylated templates for the construction of saccharide mimetics

  摘要：

  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。

  DOI：

  10.1039/c1cc13078a

文献信息

• Catalytic Aerobic Dehydrogenatin of <i>N</i> ‐Heterocycles by <i>N</i> ‐Hydoxyphthalimide
  作者：Weidong Chen、Hao Tang、Weilin Wang、Qiang Fu、Junfei Luo

  DOI：10.1002/adsc.202000767

  日期：2020.9.21

  Catalytic methods for the aerobic dehydrogenation of N‐heterocycles are reported. In most cases, indoles are accessed efficiently from indolines using catalytic N‐hydroxyphthalimide (NHPI) as the sole additive under air. Further studies revealed an improved catalytic system of NHPI and copper for the preparation of other heteroaromatics, for example quinolines.

  报道了N杂环有氧脱氢的催化方法。在大多数情况下，使用催化的N-羟基邻苯二甲酰亚胺（NHPI）作为唯一的添加剂，可以从二氢吲哚中高效地获得吲哚。进一步的研究表明，NHPI和铜的催化体系得到改进，可用于制备其他杂芳族化合物，例如喹啉。
• 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。
• Synthesis of 5- and 3-(hydroxyhexafluoroprop-2-yl)-1-(?-D-glucopyranosyl)indoles
  作者：N. D. Chkanikov、A. E. Zelenin、N. L. Brondz、M. V. Galakhov、A. F. Kolomiets、A. V. Fokin

  DOI：10.1007/bf00957531

  日期：1986.10
• 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.