2-phenyl-5-[1-(β-D-glucopyranozyl)-1,2,3-triazol-4-yl]-1,3,4-oxadiazole | 1320161-62-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-phenyl-5-[1-(β-D-glucopyranozyl)-1,2,3-triazol-4-yl]-1,3,4-oxadiazole
• 英文别名: (2R,3S,4S,5R,6R)-2-(hydroxymethyl)-6-[4-(5-phenyl-1,3,4-oxadiazol-2-yl)triazol-1-yl]oxane-3,4,5-triol
• CAS: 1320161-62-3
• 化学式: C₁₆H₁₇N₅O₆
• 分子量: 375.341
• InChiKey: UESJUXPNJMRTLB-GUYIQFIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  160
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2-ethynyl-5-phenyl-1,3,4-oxadiazole 在 sodium methylate 、 copper(II) sulfate 、 维生素 C 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 19.0h， 生成 2-phenyl-5-[1-(β-D-glucopyranozyl)-1,2,3-triazol-4-yl]-1,3,4-oxadiazole
  参考文献：
  名称：

  Synthesis of variously coupled conjugates of d-glucose, 1,3,4-oxadiazole, and 1,2,3-triazole for inhibition of glycogen phosphorylase

  摘要：

  5-(O-Perbenzoylated-beta-D-glucopyranosyl)tetrazole was obtained from O-perbenzoylated-beta-D-glucopyranosyl cyanide by Bu3SnN3 or Me3SiN3-Bu2SnO. This tetrazole was transformed into 5-ethynyl- as well as 5-chloromethyl-2-(O-perbenzoylated-beta-D-glucopyranosyl)-1,3,4-oxadiazoles by acylation with propiolic acid-DCC or chloroacetyl chloride, respectively. The chloromethyl oxadiazole gave the corresponding azidomethyl derivative on treatment with NaN3. These compounds were reacted with several alkynes and asides under Cu(I) catalysed cycloaddition conditions to give, after removal of the protecting groups by the Zemplen protocol, beta-D-glucopyranosyl-1,3,4-oxadiazolyl-1,2,3-triazole, beta-D-glucopyranosyl-1,2,3-triazolyl-1,3,4-oxadiazole, and beta-D-glucopyranosyl-1,3,4-oxadiazolylmethyl-1,2,3-triazole type compounds. 5-Phenyltetrazole was also transformed under the above conditions into a series of aryl-1,3,4-oxadiazolyl-1,2,3-triazoles, aryl-1,2,3-triazolyl-1,3,4-oxadiazoles, and aryl-1,3,4-oxadiazolylmethyl-1,2,3-triazoles. The new compounds were assayed against rabbit muscle glycogen phosphorylase b and the best inhibitors had inhibition constants in the upper micromolar range (2-phenyl-5-[1-(beta-D-glucopyranosyl)-1,2,3-triazol-4-yl]-1,3,4-oxadiazole 36: K-i = 854 mu M, 2-(beta-D-glucopyranosyl)-5-[1-(naphthalen-2-yl)-1,2,3-triazol-4-yl]-1,3,4-oxadiazole 47: K-i = 745 mu M). (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.03.004

文献信息

• Synthesis of variously coupled conjugates of d-glucose, 1,3,4-oxadiazole, and 1,2,3-triazole for inhibition of glycogen phosphorylase
  作者：Sándor Kun、Gergő Z. Nagy、Marietta Tóth、Laura Czecze、Albert Nguyen Van Nhien、Tibor Docsa、Pál Gergely、Maria-Despoina Charavgi、Paraskevi V. Skourti、Evangelia D. Chrysina、Tamás Patonay、László Somsák

  DOI：10.1016/j.carres.2011.03.004

  日期：2011.9

  5-(O-Perbenzoylated-beta-D-glucopyranosyl)tetrazole was obtained from O-perbenzoylated-beta-D-glucopyranosyl cyanide by Bu3SnN3 or Me3SiN3-Bu2SnO. This tetrazole was transformed into 5-ethynyl- as well as 5-chloromethyl-2-(O-perbenzoylated-beta-D-glucopyranosyl)-1,3,4-oxadiazoles by acylation with propiolic acid-DCC or chloroacetyl chloride, respectively. The chloromethyl oxadiazole gave the corresponding azidomethyl derivative on treatment with NaN3. These compounds were reacted with several alkynes and asides under Cu(I) catalysed cycloaddition conditions to give, after removal of the protecting groups by the Zemplen protocol, beta-D-glucopyranosyl-1,3,4-oxadiazolyl-1,2,3-triazole, beta-D-glucopyranosyl-1,2,3-triazolyl-1,3,4-oxadiazole, and beta-D-glucopyranosyl-1,3,4-oxadiazolylmethyl-1,2,3-triazole type compounds. 5-Phenyltetrazole was also transformed under the above conditions into a series of aryl-1,3,4-oxadiazolyl-1,2,3-triazoles, aryl-1,2,3-triazolyl-1,3,4-oxadiazoles, and aryl-1,3,4-oxadiazolylmethyl-1,2,3-triazoles. The new compounds were assayed against rabbit muscle glycogen phosphorylase b and the best inhibitors had inhibition constants in the upper micromolar range (2-phenyl-5-[1-(beta-D-glucopyranosyl)-1,2,3-triazol-4-yl]-1,3,4-oxadiazole 36: K-i = 854 mu M, 2-(beta-D-glucopyranosyl)-5-[1-(naphthalen-2-yl)-1,2,3-triazol-4-yl]-1,3,4-oxadiazole 47: K-i = 745 mu M). (C) 2011 Elsevier Ltd. All rights reserved.