张福义 - 郑州大学 - 化学与分子工程学院

研究领域

1. 药物合成化学开展抗癌活性糖炔金属铂化合物和糖类杂环化合物的合成及性能研究工作。合成新型糖炔铂化合物，进行生物活性测试，筛选抗癌活性先导化合物，为一类新药开发提供化学实体。己经合成并经抗癌活性测试，得到了糖炔三联吡啶铂化合物，它们的抗癌活性远大于临床使用的药物顺铂(Cisplatin)。其中，葡萄糖炔三联吡啶铂化合物对宫颈癌细胞（HeLa），肝癌细胞（HepG2），中枢神经癌细胞（SF－268），肺癌细胞（NCI－H460）和乳腺癌细胞（MCF-7）的毒性是顺铂(Cisplatin)的100倍以上，部分成果已经在Chem. Commun.和 J. Am. Chem. Soc.上发表。 2. 新型碳核苷及其类似物的合成研究在碳核苷及其类似物分子中，碱基或杂环是通过C—C键与糖基相连接的。碳核苷分子中这种C—C键不同于普通的C—O或C—N苷键，它对细菌或病毒水解酶稳定，从而能使碳核苷分子与其DNA或RNA合成酶作用，因此表现出抗菌，抗病毒，抗癌等广谱生物学活性。碳核苷及其类似物的合成研究是本课题组的研究方向之一。近期设计并合成了结构十分新颖的多种类型的碳核苷类似物，部分化合物经活性测试，对淋巴瘤的细胞毒性IC50 < 5.0 μM。这类化合物的糖基包含了几乎常见的天然糖，替代碱基的是含氮杂环。部分合成工作已经在Chem. Commun., 2014, 50 (16), 2046-2048; Chem. Commun., 2014, 50 (46), 5771-5773; J. Org. Chem,, 2014, 79, 9490-9499 上发表。 3.分枝糖﹑高碳糖和氨基糖的合成及应用分枝糖﹑高碳糖和氨基糖是三类重要的糖类化合物，分枝糖是碳链分枝通过C—C键与糖环碳相连接的，高碳糖是糖链碳原子较多的糖，这两类糖不仅具有潜在的生物学活性，而且是光学纯的手性合成子，可用于具有重要药用价值的天然产物的合成中，因此这两类化合物的合成及其应用一直受到很大重视，是十分活跃的领域。氨基糖是一类具有广谱生物活性的化合物，已经有很多氨基糖类药物在临床中使用，因此，氨基糖类药物的开发是药物化学重要领域之一。本课题组以廉价的天然糖为基本原料，旨在开发结构新型的分枝糖﹑高碳糖和氨基糖，研究它们在具有药用价值的天然产物合成中的应用。已经取得的研究成果有：（1）由葡萄糖衍生的酮糖苷与活泼亚甲基试剂缩合，在2位引入活泼双酯基，得到具有α，β不饱和共轭双酯结构的活泼中间体；利用共轭双酯基β位的亲电活性，与各种活泼亚甲基化合物反应，发现了糖环上的自动氧化-迈克尔加成反应，得到了一系列2位单链和双链同时3位被空气自动氧化的分枝糖苷，其中一些分枝糖苷可用来合成环烯醚萜类化合物及抗肿瘤蒽醌药物Adriamycinone的手性合成子。（2）在氨基糖合成方面，由氧化葡萄糖苷与脂肪胺通过羰基转位，还原反应，立体选择性地合成了一系列N－脂肪烃基取代的D－阿洛糖胺，这类化合物是合成壳聚糖酶抑制剂Allosamidin类似物的手性砌块。另外，由葡萄糖合成了一些具有抗原虫活性的2位偕氨基糖。

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Fuyi Zhang*, Yuan Xi, Yanhui Lu, Liming Wang, Linwei Liu, Jinliang Li, and Yufen Zhao, Novel syntheses of aryl quinoxaline C-nucleoside analogs by mild and efficient three-component sequential reactions, Chem. Commun., 2014, 50 (43), 5771 – 5773. Fuyi Zhang*, Liming Wang, Cui Zhang, and Yufen Zhao, Novel regio- and stereoselective phosphonyl radical addition to glycals promoted by Mn(II)–air: syntheses of 1,2-dideoxy 2-C-diphenylphosphinylglycopyranosides, Chem. Commun., 2014, 50（16）, 2046—2048. Fuyi Zhang*, Delong Mu, Liming Wang, Pengfei Du, Fen Han, and Yufen Zhao, Synthesis of Substituted Mono- and Diindole C-Nucleoside Analogues from Sugar Terminal Alkynes by Sequential Sonogashira/Heteroannulation Reaction, J. Org. Chem,, 2014, 79, 9490-9499. Jun Yu, Jiansong Sun, Yiming Niu, Rongyao Li, Jinxi Liao, Fuyi Zhang and Biao Yu*, Synthetic access toward the diverse ginsenosides, Chem. Sci., 2013, 4, 3899-3905. Fuyi Zhang*, Hong Liu, Yingming Sheng, Hongmin Liu, Synthesis of 2, 2-Bis-C- functionalized Chain Glucosid-3-ketals, Chin. J. Chem., 2012, 30, 195-198. Hong Liu, Fuyi Zhang*, Jin-Peng Li, Xuebin Yan, Hong-Min Liu, Yu-Fen Zhao，Novel Methyl 4,6-O-benzylidene-3-ketoglucopyranosid-fused γ-lactam: Synthesis and Crystal Structure，J. Chem. Crystallogr., 2011, 41, 1228–1231. Qingju Zhang, Jiansong Sun, Yugen Zhu, Fuyi Zhang, Biao Yu*, An Efficient Approach to the Synthesis of Nucleosides: Gold(I)-Catalyzed N-Glycosylation of Pyrimidines and Purines with Glycosyl ortho-Alkynyl Benzoates, Angew. Chem. Int. Ed., 2011, 50(21), 4933-4936. Fuyi Zhang*, Yu-Xin Wang, Feng-Ling Yang, Hong-Yu Zhang, Yu-Fen Zhao, An Efficient Solvent-free Knoevenagel Condensation between β-diketone and Aldehyde Catalyzed by Silica Sulfuric Acid, Synth. Commun., 2011, 41(3), 347-356. Fuyi Zhang*, Hong Liu, Qing-Ju Zhang, Yu-Fen Zhao, Feng-Ling Yang, Silica phosphoric acid: an efficient and recyclable catalyst for the solvent-free synthesis of acylals and their deprotection, Synth. Commun., 2010, 40(21), 3240-3250. Fuyi Zhang*, Hong Liu, Yong-Feng Li, Hong-Min Liu, Novel synthesis of methyl 4,6-O-benzylidenespiro[2-deoxy-α-d-arabino-hexopyranoside-2,2′-imidazolidine] and its homologue and sugar-γ-butyrolactam derivatives from methyl 4,6-O-benzylidene-α- D-arabino-hexopyranosid-2-ulose, Carbohydr. Res., 2010, 345, 839-843. Fuyi Zhang*, Chun Li Wu, Cui Zhang, Hong Min Liu, Stereoselective synthesis and crystal structure of 4,6-O- benzylidene-N-octyl-D-allosamine hydrochloride, Chin. Chem. Lett., 2010, 21, 798-801. Qingju Zhang, Jiansong Sun, Fuyi Zhang, and Biao Yu, Synthesis of Sugar-Fused Isoxazoline N-Oxides from 2-Nitroglycals, Eur. J. Org. Chem., 2010, 3579-3582. Chi-Ming Ho, Jun-Long Zhang, Cong-Ying Zhou, On-Yee Chan, Jessie Jing Yan, Fuyi Zhang, Jie-Sheng Huang and Chi-Ming Che*, A Water-Soluble Ruthenium Glycosylated Porphyrin Catalyst for Carbenoid Transfer Reactions in Aqueous Media with Applications in Bioconjugation Reactions, J. Am. Chem. Soc., 2010, 132 (6), 1886–1894. Fuyi Zhang, Bruno Bernet, Véronique Bonnet, Andrea Vasella*, 6-(Diazomethyl) -1,3-bis(methoxymethyl)uracil, synthesis and transformation into annulated pyrimidinediones, Helv. Chim. Acta, 2008, 91(7),1201-1218. Fuyi Zhang, Shikha Rani, Bruno Bernet, Andrea Vasella*, 2-Azido-2-deoxycellulose: synthesis and 1,3-dipolar cycloaddition, Helv. Chim. Acta, 2008, 91(4), 608-618. Fuyi Zhang, Andrea Vasella*, Regioselective synthesis of 1I,1II,5I,5II,6I,6I,6II,6II- 2H8- cellobiose, Carbohydr. Res., 2007, 342 (7), 2546-2556. Dik-Lung Ma, Tina Yuen-Ting Shum, Fuyi Zhang, Chi-Ming Che*, Water soluble luminescent platinum terpyridine complexes with glycosylated acetylide and arylacetylide ligands: photoluminescent properties and cytotoxicities, Chem. Commun., 2005, 4675-4677. Hong-Min Liu, Fuyi Zhang, Da-Peng Zou, Stereoselective synthesis of 2,2-bis(C-branched-chain)glucopyranosid-3-ulose via an autoxidation-Michael addition reaction, Chem. Commun., 2003, 2044-2045. Hong-Min Liu, Fuyi Zhang, Shaomin Wang, Stereoselective synthesis of 2-amino-2-deoxysugars: N-alkyl-D-allosamines, Org. Biomol. Chem., 2003, 1, 1641-1642. Hong-Min Liu, Fuyi Zhang, Jianye Zhang, Novel autoxidation and Michael addition mechanism of a butenolide-containing sugar leading to a C-branched chain glucopyranosidulose, and X-ray structure of intermediates, Carbohydr. Res., 2003, 338, 1737-1743.