S-cyanomethyl 2-N-acetamido-2-deoxy-1-thio-β-D-glucopyranoside | 61145-38-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: S-cyanomethyl 2-N-acetamido-2-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: N-[(2S,3R,4R,5S,6R)-2-(cyanomethylsulfanyl)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 61145-38-8
• 化学式: C₁₀H₁₆N₂O₅S
• 分子量: 276.313
• InChiKey: NWSYWLAZPURYLH-IGORNWKESA-N

物化性质

• 熔点：
  173.5-174.2 °C(Solv: methanol (67-56-1))
• 沸点：
  638.3±55.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  148
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  S-cyanomethyl 2-N-acetamido-2-deoxy-1-thio-β-D-glucopyranoside 在 吡啶 、 2,6-二叔丁基-4-甲基吡啶 、 silver trifluoromethanesulfonate 、 triethylamine tris(hydrogen fluoride) 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.5h， 生成 S-cyanomethyl 2-N-acetimido-6-O-acetyl-3-O-[2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl]-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  [EN] DRUG DELIVERY
  [FR] ADMINISTRATION DE MÉDICAMENT

  摘要：

  一种药物传递载体，包括与一个或多个靶向基团结合的囊泡，其中该靶向基团包括Lewis A或Lewis B或其类似物的寡糖，或者是该寡糖的药用可接受盐或PEG化形式：（I）其中R代表与囊泡的连接点。

  公开号：

  WO2019211595A1
• 作为产物：
  描述：

  2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranosyl chloride 在 甲醇 、 sodium dithionite 、 potassium carbonate 、 三乙胺 作用下， 以 水 、 丙酮 为溶剂， 反应 42.0h， 生成 S-cyanomethyl 2-N-acetamido-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  [EN] DRUG DELIVERY
  [FR] ADMINISTRATION DE MÉDICAMENT

  摘要：

  一种药物传递载体，包括与一个或多个靶向基团结合的囊泡，其中该靶向基团包括Lewis A或Lewis B或其类似物的寡糖，或者是该寡糖的药用可接受盐或PEG化形式：（I）其中R代表与囊泡的连接点。

  公开号：

  WO2019211595A1

文献信息

• [EN] INFLAMMATION IMAGING AND THERAPY<br/>[FR] IMAGERIE ET THÉRAPIE D'UNE INFLAMMATION
  申请人：ISIS INNOVATION

  公开号：WO2014027203A1

  公开（公告）日：2014-02-20

  An imaging agent comprising a conjugate of an oligosaccharide moiety with an imaging moiety. The oligosaccharide is Lewis A or Lewis B or a mimetic thereof, or a pharmaceutically acceptable salt or PEGylated form of Lewis A or Lewis B or its mimetics. Lewis A and Lewis B and its mimetics are also provided for use in the therapeutic treatment of inflammatory diseases, autoimmune diseases and cancer.

  一种成像剂，包括寡糖基团与成像基团的结合物。该寡糖为Lewis A或Lewis B或其模拟物，或Lewis A或Lewis B或其模拟物的药用盐或PEG化形式。Lewis A和Lewis B及其模拟物还可用于治疗炎症性疾病、自身免疫疾病和癌症。
• INFLAMMATION IMAGING AND THERAPY
  申请人：Isis Innovation Limited

  公开号：US20150231281A1

  公开（公告）日：2015-08-20

  An imaging agent comprising a conjugate of an oligosaccharide moiety with an imaging moiety. The oligosaccharide is Lewis A or Lewis B or a mimetic thereof, or a pharmaceutically acceptable salt or PEGylated form of Lewis A or Lewis B or its mimetics. Lewis A and Lewis B and its mimetics are also provided for use in the therapeutic treatment of inflammatory diseases, autoimmune diseases and cancer.

  一种成像剂，包括具有寡糖基团和成像基团的共轭物。寡糖是Lewis A或Lewis B或其类似体，或者是Lewis A或Lewis B或其类似体的药用盐或PEG化形式。还提供了Lewis A和Lewis B及其类似体，用于治疗炎症性疾病、自身免疫性疾病和癌症。
• Inflammation imaging and therapy
  申请人：Isis Innovation Limited

  公开号：US10016518B2

  公开（公告）日：2018-07-10

  An imaging agent comprising a conjugate of an oligosaccharide moiety with an imaging moiety. The oligosaccharide is Lewis A or Lewis B or a mimetic thereof, or a pharmaceutically acceptable salt or PEGylated form of Lewis A or Lewis B or its mimetics. Lewis A and Lewis B and its mimetics are also provided for use in the therapeutic treatment of inflammatory diseases, autoimmune diseases and cancer.

  一种成像剂，包含寡糖分子与成像分子的共轭物。寡糖是路易斯 A 或路易斯 B 或其模拟物，或路易斯 A 或路易斯 B 或其模拟物的药学上可接受的盐或 PEG 化形式。Lewis A 和 Lewis B 及其模拟物还可用于炎症性疾病、自身免疫性疾病和癌症的治疗。
• In vivo behaviour of glyco-NaI@SWCNT ‘nanobottles’
  作者：Sonia De Munari、Stefania Sandoval、Elzbieta Pach、Belén Ballesteros、Gerard Tobias、Daniel C. Anthony、Benjamin G. Davis

  DOI：10.1016/j.ica.2019.05.032

  日期：2019.9

  Carbon nanotubes are appealing imaging and therapeutic systems. Their structure allows not only a useful display of molecules on their outer surface but at the same time the protection of encapsulated cargoes. Despite the interest they have provoked in the scientific community, their applications have not yet been fully realised due to the limited knowledge we possess concerning their physiological behaviour. Previously, we have shown that the encapsulation of radionuclide in the inner space of glycan-functionalized single-walled carbon nanotubes (glyco-X@SWCNT) redirected in vivo distribution of radioactivity from the thyroid to the lungs. Here we test the roles played by such glycans attached to carbon nanotubes in controlling sites of accumulation using nanotubes carrying both 'cold' and 'hot' salt cargoes decorated with two different mammalian carbohydrates, N-acetyl-D-glucosamine (GlcNAc) or galactose (Gal)-capped disaccharide lactose (Gal-Glc). This distinct variation of the terminal glycan displayed between two types of glycan ligands with very different in vivo receptors, coupled with altered sites of administration, suggest that distribution in mammals is likely controlled by physiological mechanisms that may include accumulation in the first capillary bed they encounter and not by glycan-receptor interaction and that the primary role of glycan is in aiding the dispersibility of the CNTs.