3,4,6-tri-O-acetyl-1,2-dideoxy-2'-azidomethyl-α-D-glucopyrano-[2,1-d]-Δ2'-thiazoline | 944070-33-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-acetyl-1,2-dideoxy-2'-azidomethyl-α-D-glucopyrano-[2,1-d]-Δ2'-thiazoline
• 英文别名: 1,3,4,6-tetra-O-acetyl-1,2-dideoxy-2'-azidomethyl-α-D-glucopyranosyl-[2,1-d]-Δ2'-thiazoline；[(3aR,5R,6S,7R,7aR)-6,7-diacetyloxy-2-(azidomethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazol-5-yl]methyl acetate
• CAS: 944070-33-1
• 化学式: C₁₄H₁₈N₄O₇S
• 分子量: 386.386
• InChiKey: JHTAIZGDBRFTRU-DKTYCGPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-acetyl-1,2-dideoxy-2'-azidomethyl-α-D-glucopyrano-[2,1-d]-Δ2'-thiazoline 在 甲醇 、 sodium methylate 作用下， 反应 0.5h， 以90%的产率得到(3aR,5R,6S,7R,7aR)-2-(azidomethyl)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol
  参考文献：
  名称：

  Tautomeric Modification of GlcNAc-Thiazoline

  摘要：

  The potent O-GlcNAcase (OGA) inhibitor GlcNAc-thiazoline has been modified by buffer- or acylation-induced imine-to-enamine conversion and then electrophile or radical addition (X-n = D-3, F, N-3, OH, SMe, COCF3, CF3). Several functionalized GlcNAc-thiazolines show highly selective inhibition of OGA vs human hexosaminidase and thus have promise as tools for targeted investigations of OGA, an enzyme linked to diabetes and neurodegeneration. A new radical addition/fragmentation reaction of the N-(trifluoroacetyl)enamine has been discovered.

  DOI：

  10.1021/ol0706814
• 作为产物：
  描述：

  [(3aR,5R,6S,7R,7aR)-6,7-diacetyloxy-2-(iodomethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazol-5-yl]methyl acetate 在 sodium azide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以90%的产率得到3,4,6-tri-O-acetyl-1,2-dideoxy-2'-azidomethyl-α-D-glucopyrano-[2,1-d]-Δ2'-thiazoline
  参考文献：
  名称：

  Tautomeric Modification of GlcNAc-Thiazoline

  摘要：

  The potent O-GlcNAcase (OGA) inhibitor GlcNAc-thiazoline has been modified by buffer- or acylation-induced imine-to-enamine conversion and then electrophile or radical addition (X-n = D-3, F, N-3, OH, SMe, COCF3, CF3). Several functionalized GlcNAc-thiazolines show highly selective inhibition of OGA vs human hexosaminidase and thus have promise as tools for targeted investigations of OGA, an enzyme linked to diabetes and neurodegeneration. A new radical addition/fragmentation reaction of the N-(trifluoroacetyl)enamine has been discovered.

  DOI：

  10.1021/ol0706814

文献信息

• 糖基噻唑啉化合物及其制备方法和应用
  申请人：中国农业大学

  公开号：CN104447894B

  公开（公告）日：2016-10-12

  本发明公开了一种糖基噻唑啉化合物及其制备方法和应用。所述糖基噻唑啉化合物的结构式如式(I)或式(II)所示。本发明所述糖基噻唑啉化合物或其药学上可接受的盐除具有良好杀菌活性的同时，还对α‑葡萄糖苷酶具有较好的抑制活性，部分化合物的抑制活性超过对照药剂阿卡波糖。
• Synthesis of NAG-thiazoline-derived inhibitors for β-N-acetyl-d-hexosaminidases
  作者：Hanchu Kong、Wei Chen、Huizhe Lu、Qing Yang、Yanhong Dong、Daoquan Wang、Jianjun Zhang

  DOI：10.1016/j.carres.2015.06.004

  日期：2015.9

  beta-N-Acetyl-D-hexosaminidases are responsible for the metabolism of glycoconjugates in diverse physiological processes that are important targets for medicine and pesticide development. Fourteen new NAG-thiazoline derivatives were synthesized by cyclization and click reaction using D-glucosamine hydrochloride as the starting material. All the compounds created were characterized by NMR and HRMS spectra. A preliminary bioassay, using four enzymes from two beta-N-acetyl-D-hexosaminidase families, showed that most of the compounds synthesized exhibit selective inhibition of GH84 beta-N-acetyl-D-hexosaminidase. Among the compounds tested, compounds 5a (IC50 = 12.6 mu M, hOGA) and 5e (IC50 = 12.5 mu M, OfOGA) proved to be a highly selective and potent inhibitor. (C) 2015 Elsevier Ltd. All rights reserved.