4-[1-(β-D-galactopyranosyl)-1H-1,2,3-triazol-4-yl](4-methoxyphenyl) | 1186419-65-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-[1-(β-D-galactopyranosyl)-1H-1,2,3-triazol-4-yl](4-methoxyphenyl)
• 英文别名: 1-(β-D-galactopyranosyl)-4-(p-methoxyphenyl)-1,2,3-triazole；(2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-[4-(4-methoxyphenyl)triazol-1-yl]oxane-3,4,5-triol
• CAS: 1186419-65-7
• 化学式: C₁₅H₁₉N₃O₆
• 分子量: 337.332
• InChiKey: BDGJXKOMXNXPDQ-GZBLMMOJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  130
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-叠氮-1-脱氧-β-D-吡喃半乳糖苷四乙酸酯 在 [Cu(tBuBz₃tren)ketoprofenate]ketoprofenate 、 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 26.5h， 生成 4-[1-(β-D-galactopyranosyl)-1H-1,2,3-triazol-4-yl](4-methoxyphenyl)
  参考文献：
  名称：

  光诱导电子转移驱动的铜催化剂活化：一种原型光潜点击催化剂

  摘要：

  宠物猫。酮基丙酸铜（II）预催化剂1（参见图片）在室温下在甲醇中无活性，但在光照射下会定量迅速地还原成亚铜状态，从而提供高反应性的点击催化剂。通过简单地将空气引入反应介质中，可以关闭催化剂，然后通过鼓泡氩气然后辐照再次打开催化剂。

  DOI：

  10.1002/anie.201203014

文献信息

• Synthesis and biological evaluation of 11C-labeled β-galactosyl triazoles as potential PET tracers for in vivo LacZ reporter gene imaging
  作者：Sofie Celen、Jan Cleynhens、Christophe Deroose、Tjibbe de Groot、Abdelilah Ibrahimi、Rik Gijsbers、Zeger Debyser、Luc Mortelmans、Alfons Verbruggen、Guy Bormans

  DOI：10.1016/j.bmc.2009.05.056

  日期：2009.7

  In our aim to develop LacZ reporter probes with a good retention in LacZ expressing cells, we report the synthesis and preliminary evaluation of two carbon-11 labeled beta-galactosyl triazoles 1-(beta-D-galactopyranosyl)4-(p-[C-11]methoxyphenyl)-1,2,3-triazole ([C-11]-6) and 1-(beta-D-galactopyranosyl)-4-(6-[C-11]methoxynaphthyl)-1,2,3-triazole ([C-11]-13). The precursors for the radiolabeling and the non-radioactive analogues (6 and 13) were synthesized using straightforward 'click' chemistry. In vitro incubation experiments of 6 with beta-galactosidase in the presence of o-nitrophenyl beta-D-galactopyranoside (ONPG) showed that the triazolic compound was an inhibitor of beta-galactosidase activity. Radiolabeling of both precursors was performed using [C-11] methyl iodide as alkylating agent at 70 degrees C in DMF in the presence of a small amount of base. The log P values were -0.1 and 1.4, respectively, for [C-11]-6 and [C-11]-13, the latter therefore being a good candidate for increased cellular uptake via passive diffusion. Biodistribution studies in normal mice showed a good clearance from blood for both tracers. [C-11]-6 was mainly cleared via the renal pathway, while the more lipophilic [C-11]-13 was excreted almost exclusively via the hepatobiliary system. Despite the lipophilicity of [C-11]-13, no brain uptake was observed. Reversed phase HPLC analysis of murine plasma and urine revealed high in vivo stability for both tracers. In vitro evaluation in HEK-293T cells showed an increased cell uptake for the more lipophilic [C-11]-13, however, there was no statistically higher uptake in LacZ expressing cells compared to control cells. (C) 2009 Elsevier Ltd. All rights reserved.
• Copper Catalyst Activation Driven by Photoinduced Electron Transfer: A Prototype Photolatent Click Catalyst
  作者：Lydie Harmand、Sarah Cadet、Brice Kauffmann、Luca Scarpantonio、Pinar Batat、Gediminas Jonusauskas、Nathan D. McClenaghan、Dominique Lastécouères、Jean-Marc Vincent

  DOI：10.1002/anie.201203014

  日期：2012.7.16

  PET cat. While the copper(II) tren ketoprofenate precatalyst 1 (see picture) is inactive at room temperature in methanol, it is quantitatively and rapidly reduced to its cuprous state upon light irradiation to provide a highly reactive click catalyst. By simply introducing air into the reaction medium the catalysis can be switched off and then switched on again by bubbling argon followed by irradiation

  宠物猫。酮基丙酸铜（II）预催化剂1（参见图片）在室温下在甲醇中无活性，但在光照射下会定量迅速地还原成亚铜状态，从而提供高反应性的点击催化剂。通过简单地将空气引入反应介质中，可以关闭催化剂，然后通过鼓泡氩气然后辐照再次打开催化剂。