Development of alpha 1,6-fucosyltransferase inhibitors through the diversity-oriented syntheses of GDP-fucose mimics using the coupling between alkyne and sulfonyl azide

Manabe Yoshiyuki; Kasahara Satomi; Takakura Yohei; Yang Xiaoxiao; Takamatsu Shinji; Kamada Yoshihiro; Miyoshi Eiji; Yoshidome Daisuke; Fukase Koichi

首页> 外文期刊>Bioorganic and medicinal chemistry >Development of alpha 1,6-fucosyltransferase inhibitors through the diversity-oriented syntheses of GDP-fucose mimics using the coupling between alkyne and sulfonyl azide

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Development of alpha 1,6-fucosyltransferase inhibitors through the diversity-oriented syntheses of GDP-fucose mimics using the coupling between alkyne and sulfonyl azide

机译：使用炔烃和磺酰叠氮化物之间的偶联来研制α1,6-岩氧基转移酶抑制剂通过多样化的GDP - 岩藻糖模拟的合成

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We developed alpha 1,6-fucosyltransferase (FUT8) inhibitors through a diversity-oriented synthesis. The coupling reaction between the fucose unit containing alkyne and the guanine unit containing sulfonyl azide under various conditions afforded a series of Guanosine 5'-diphospho-beta-L-fucose (GDP-fucose) analogs. The synthesized compounds displayed FUT8 inhibition activity. A docking study revealed that the binding mode of the inhibitor synthesized with FUT8 was similar to that of GDP-fucose. (C) 2017 Elsevier Ltd. All rights reserved.

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来源
《Bioorganic and medicinal chemistry》 |2017年第11期|共7页
作者
Manabe Yoshiyuki; Kasahara Satomi; Takakura Yohei; Yang Xiaoxiao; Takamatsu Shinji; Kamada Yoshihiro; Miyoshi Eiji; Yoshidome Daisuke; Fukase Koichi;
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作者单位

Osaka Univ Grad Sch Sci Dept Chem 1-1 Machikaneyama Toyonaka Osaka 5600043 Japan;

Osaka Univ Grad Sch Sci Dept Chem 1-1 Machikaneyama Toyonaka Osaka 5600043 Japan;

Osaka Univ Grad Sch Sci Dept Chem 1-1 Machikaneyama Toyonaka Osaka 5600043 Japan;

Osaka Univ Grad Sch Sci Dept Chem 1-1 Machikaneyama Toyonaka Osaka 5600043 Japan;

Osaka Univ Grad Sch Med Div Hlth Sci 1-7 Yamadaoka Suita Osaka 5650871 Japan;

Osaka Univ Grad Sch Med Div Hlth Sci 1-7 Yamadaoka Suita Osaka 5650871 Japan;

Osaka Univ Grad Sch Med Div Hlth Sci 1-7 Yamadaoka Suita Osaka 5650871 Japan;

Schrodinger KK Chiyoda Ku 17F Marunouchi Trust Tower North 1-8-1 Marunouchi Tokyo 1000005 Japan;

Osaka Univ Grad Sch Sci Dept Chem 1-1 Machikaneyama Toyonaka Osaka 5600043 Japan;

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原文格式 PDF
正文语种 eng
中图分类药学;
关键词
Glycosyltransferase inhibitor; alpha 1; 6-Fucosyltransferase; Diversity-oriented synthesis; Sulfonyl azide;

机译：糖基转移酶抑制剂;α1;6-岩藻糖基转移酶;定向定向的合成;磺酰叠氮化物;

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专利

1. Development of alpha 1,6-fucosyltransferase inhibitors through the diversity-oriented syntheses of GDP-fucose mimics using the coupling between alkyne and sulfonyl azide [J] . Manabe Yoshiyuki, Kasahara Satomi, Takakura Yohei, Bioorganic and medicinal chemistry . 2017,第11期

机译：使用炔烃和磺酰叠氮化物之间的偶联来研制α1,6-岩氧基转移酶抑制剂通过多样化的GDP - 岩藻糖模拟的合成
2. Copper(I)-Catalyzed [3 + 2] Cycloaddition/Ring-Opening Rearraegement/[4+2]Cycloaddition/Aromatization Cascade: An Unprecedented Chemo-and Stereoselective Three Component Coupling of Sulfonyl Azide, Alkyne and N-Arylidenepyridin-2-amine to Pyrido[1,2-a]pyrimidin-4-imine [J] . Kayambu Namitharan, Kasi Pitchumani Advanced synthesis & catalysis . 2013,第1期

机译：铜（I）催化的[3 + 2]环加成/开环重排/ [4 + 2]环加成/芳构化级联：前所未有的化学和立体选择性三组分偶联的磺酰基叠氮化物，炔烃和N-亚苄基吡啶-2-胺吡啶并[1,2-a]嘧啶-4-亚胺
3. Porous metal-organic framework catalyzing the three-component coupling of sulfonyl azide, alkyne, and amine [J] . Yang T., Cui H., Zhang C., Inorganic Chemistry: A Research Journal that Includes Bioinorganic, Catalytic, Organometallic, Solid-State, and Synthetic Chemistry and Reaction Dynamics . 2013,第15期

机译：多孔金属-有机骨架催化磺酰叠氮化物，炔烃和胺的三组分偶联
4. Development of fucosyltransferase and fucosidase inhibitors by structure- and screening-based approaches [C] . Chun-Hung Hans Lin, Zhijay Tu International Carbohydrate Symposium . 2013

机译：通过结构和筛选方法研制岩氧基转移酶和岩藻糖苷酶抑制剂
5. I) The Development of Deoxycytidine Kinase Inhibitors with Nanomolar Affinity and Improved Metabolic Stability. II) The Synthesis of Ferrocene-Containing Monomers and Biodegradable Polymers Using Azide-Alkyne Click Chemistry and Ring Opening Polymerization [D] . Gipson, Raymond Marshall 2015

机译：I）具有纳摩尔摩尔亲和力和改善的代谢稳定性的脱氧胞苷激酶抑制剂的开发。 II）使用叠氮化物-炔烃Click化学和开环聚合反应合成含二茂铁的单体和可生物降解的聚合物
6. Arborescent Unimolecular Micelles: Poly(γ-Benzyl l-Glutamate) Core Grafted with a Hydrophilic Shell by Copper(I)-Catalyzed Azide–Alkyne Cycloaddition Coupling [O] . Mario Gauthier, Greg Whitton 2017

机译：呈树状的单分子胶束：铜（I）催化的叠氮化物-炔烃环加成偶联接枝亲水壳的聚（γ-苄基-1-谷氨酸酯）核
7. Highly Efficient One-Pot Synthesis of N-Sulfonylamidines by Cu-Catalyzed Three-Component Coupling of Sulfonyl Azide, Alkyne, and Amine [O] . -1

机译：通过Cu催化的磺酰叠氮化物，炔烃和胺的Cu催化三组分偶联高效一罐合成N-磺酰酰胺

Development of alpha 1,6-fucosyltransferase inhibitors through the diversity-oriented syntheses of GDP-fucose mimics using the coupling between alkyne and sulfonyl azide

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