Concise synthesis of oxy-bridged bicyclic azasugar and thiosugar as potential glycosidase inhibitors

Abstract

Abstract:

Aim To develop a concise method for the synthesis of bicyclic azasugar and thiosugar with novel scaffold. Methods The two primary hydroxyl groups of compound 1 were selectively protected with tosyl cloloride in pyridine, followed by ring-closure with sodium sulfide or primary amine to form the oxy-bridged bicyclic molecules in good yields. Results Two bicyclic azasugars and a thiosugar were produced from L-sorbose in several steps. Conclusion The described procedures provide an efficient method to synthesize bicyclic azasugar and thiosugar with novel scaffold as potential glycosidase inhibitors.

Key words: Oxy-bridge, Oxy-bridge, Bicyclic azasugar, Bicyclic azasugar, Bicyclic thiosugar, Bicyclic thiosugar, Ring-closure, Ring-closure

CLC Number:

R916.41

Supporting:

Xiang-Bao Meng, Yan-Ping Li, Zhong-Jun Li^*. Concise synthesis of oxy-bridged bicyclic azasugar and thiosugar as potential glycosidase inhibitors[J]. .

References

[1] Hoffman DJ, Whistler RL Diabetogenic action of 5-thioglucopyranose in rats [J]. Biochemistry, 1968, 7 (12): 4479–4483.
[2] Wong CH, Ichikawa YK, T Narvor CGL, et al. Probing the acceptor specificity of beta-1,4-galactosyltransferase for the development of enzymatic synthesis of novel oligosaccharides [J]. J Am Chem Soc, 1991, 113 (21): 8137– 8145.
[3] Merrer YL, Fuzier M, Dosbaa I, et al. Synthesis of thiosugars as weak inhibitors of glycosidases [J]. Tetrahedron, 1997, 53 (49) : 16731–16746.
[4] Johnston BD, Pinto BM. Synthesis of 1,2-and 1,3-N-linked disaccharides of 5-thio-α-D–mannopyranose as potential inhibitors of the processing mannosidase class I and mannosidase II enzymes [J]. J Org Chem, 1998, 63 (17): 5797– 5800.
[5] Yoshikawa M, Morikawa T, Matsuda H, et al; Absolute stereostructure of potent α-glucosidase inhibitors, salinol, with unique thiosugar sulfonium sulfate inner salt structure from salacia reticulata [J]. Bioorg Med Chem, 2002, 10: 1547– 1554.
[6] Johnston BD, Jensen HK, Pinto BM. Synthesis of sulfonium sulfate analogues of disaccharides and their conversion to chain-extented homologues of salacinol: newglycosidase inhibitors [J]. J Org Chem, 2006, 71 (3): 1111–1118.
[7] Afarinkia K, Bahar A. Recent advances in the chemistry of azapyranose sugars [J]. Tetrahedron: Asymmetry, 2005, 16 (7): 1239– 1287.
[8] Pearson MSM, Mathé-Allainmat M, Fargeas V, et al, Recent advances in the total synthesis of piperdine azasugars [J]. Eur J Org Chem, 2005, (11) : 2159–2191.
[9] Asano N. Naturally occurring iminosugars and related compounds: structure, distribution, and biological activity [J]. Curr Top Med Chem, 2003, 3 (5): 471–484.
[10] Greimel P, Spreitz J, Stütz AE, et al; Iminosugars and relatives as antiviral and potential anti-infective agents [J]. Curr Top Med Chem, 2003, 3 (5): 513–523.
[11] Butters TD, Dwek RA, Platt FM. Therapeutic applications of imino sugars in lysosomal storage disorders [J]. Curr Top-Med Chem, 2003, 3 (5): 561–574.
[12] An JN, Meng XB, Yao Y; et al. A facile synthesis of 1, 6–dideoxynojirimycin from L–sorbose [J]. Carbohydrate Res, 2006, 341: 2200–2203.

[1]	Chao Li, Ying Guo, Chao Tian, Shouxin Zhou, Rufeng Yan, Zhili Zhang, Xiaowei Wang, Junyi Liu^*. Expression, purification and activity assay of recombinant human thymidylate synthase [J]. , 2013, 22(2): 173-176.
[2]	Chao Tian, Zhi-Li Zhang, Jun-Yi Liu^* . Synthesis and evaluation of 8-deaza-5,6,7,8-tetrahydromethotrexate derivatives as dihydrofolate reductase inhibitors [J]. , 2012, 21(2): 142-148.
[3]	Jing-Qian Jiang, Zheng-Ren Xu, Yan-Xing Jia^*. CuI-catalyst N-arylation of 4-iodotryptophan derivatives: effort toward the total synthesis of indolactam V [J]. , 2012, 21(2): 113-123.
[4]	Liang-Liang Shi, Hai-Nan Wei, Chang-Mei Cheng^, Lang-Qiu Chen^, Yi-Gang Tong . Synthesis of telbivudine 3'-O-acetyl-5'-O-phenyl-N-alkylphosphramidates and evaluation of their anti-HBV activities [J]. , 2011, 20(5): 454-459.
[5]	Ai-Li Fan, Wen-Han Lin, Yan-Xing Jia^*. Recent progress in the research on lamellarins and related pyrrole-derived alkaloids from marine organisms [J]. , 2011, 20(5): 425-441.
[6]	Qing Li, Yue-Tao Zhao, Xiang-Bao Meng, Ting-Ting Yan, Shu-Chun Li, He-Qing Huang, Zhi-Hui Zhao^, Zhong-Jun Li^ . Synthesis of two multivalent lactosides with anti-adhesive activity and their fluorescein-labeled and biotin-labeled derivatives [J]. , 2011, 20(4): 325-334.
[7]	Rui Sun, Jing Song, Hui Zhao, Chun-Li Yan, Ai-Jun Zhang, Diwa Koirala, Da-Wei Li, Chun Hu^*. Synthesis and anti-tumor activity of 1,4-dihydrothieno[3',2':5,6]thiopyrano[4,3-c]pyrazole-3-carboxylic amide derivatives [J]. , 2011, 20(1): 32-36.
[8]	Gong Li, Qi Sun, Jing-Rong Cui, Run-Tao Li^. Modification of the alkylating agent chlorambucil with spiropiperazinium salts [J]. , 2010, 19(5): 346-352.
[9]	Yu Zheng, Xiang-Bao Meng, Shu-Chun Li, He-Qing Huang, Zhong-Jun Li^, Qing Li^ . Synthesis and anti-tumor activities of 5-carbohydrate modified cyclophosphamide derivates [J]. , 2010, 19(5): 327-340.
[10]	Rui-Juan Xing, Li Pan, Xi Wen, Jian Wang, Mao-Sheng Cheng^* . A practical and efficient procedure for the α-bromination of arylethanones [J]. , 2010, 19(5): 400-402.
[11]	Li Li, Hua Qin, Liang Zhang, Xiao-Wei Wang, Jun-Yi Liu^* . Study on the iodination of uracil derivatives [J]. , 2010, 19(2): 146-150.
[12]	Hao Zou, Hao Jiang, Jie-Yun Zhou, Yan Zhu^, Lin Cao, Peng Xia, Qian Zhang^ . Synthesis of 3-(4-hydroxyphenyl)-4-methyl-6-methoxy-7-hydroxycoumarin and its analogues as angiogenesis inhibitors [J]. , 2010, 19(2): 136-140.
[13]	Qing Yang, Ji-Rang Zhu, Qi Sun^, Jing-Rong Cui, Run-Tao Li, Ze-Mei Ge^ . A novel class of cyclophosphamide prodrug: structure-activity relationships of cyclophosphamide piperaziniums [J]. , 2010, 19(1): 24-33.
[14]	Zheng-Yan Cai^*, Jing Pan, Qun Hao, Wei-Cheng Zhou, Lu-Yong Zhang. Synthesis of 4-phenoxy quinoline mevalonolactones and evaluation of their HMG CoA reductase inhibition activities [J]. , 2010, 19(1): 15-23.
[15]	Jing Li, Jia-Ning Fu, Qiang Tan, Hui-Hui Zeng^* . Synergistic effect of ethaselen and cisplatin treatment against tumor cell lines [J]. , 2009, 18(4): 337-341.