Design, synthesis and bioactivity of N-glycosyl-N'-(5-substituted phenyl-2-furoyl) hydrazide derivatives

Zining Cui; Hang Su; Jiazhen Jiang; Xinling Yang; Yoshihiro Nishida

doi:10.3390/ijms15046741

Design, synthesis and bioactivity of N-glycosyl-N'-(5-substituted phenyl-2-furoyl) hydrazide derivatives

Int J Mol Sci. 2014 Apr 21;15(4):6741-56. doi: 10.3390/ijms15046741.

Authors

Zining Cui¹, Hang Su², Jiazhen Jiang³, Xinling Yang⁴, Yoshihiro Nishida⁵

Affiliations

¹ Guangdong Province Key Laboratory of Microbial Signals and Disease Control, Department of Plant Pathology, College of Natural Resources and Environment, South China Agricultural University, Guangzhou 510642, China. ziningcui@scau.edu.cn.
² Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. kongkong_1989@sina.cn.
³ Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. 97066h@cau.edu.cn.
⁴ Department of Applied Chemistry, College of Science, China Agricultural University, Beijing 100193, China. yangxl@cau.edu.cn.
⁵ Division of Nanobiology, Advanced Integrated Science, Chiba University, Matsudo, Chiba 271-0092, Japan. ynishida@faculty.chiba-u.jp.

Abstract

Condensation products of 5-substituted phenyl-2-furoyl hydrazide with different monosaccharides D-glucose, D-galactose, D-mannose, D-fucose and D-arabinose were prepared. The anomerization and cyclic-acyclic isomers were investigated by 1H NMR spectroscopy. The results showed that, except for the d-glucose derivatives, which were in the presence of β-anomeric forms, all derivatives were in an acyclic Schiff base form. Their antifungal and antitumor activities were studied. The bioassay results indicated that some title compounds showed superior effects over the commercial positive controls.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antifungal Agents* / chemical synthesis
Antifungal Agents* / chemistry
Antifungal Agents* / pharmacology
Antineoplastic Agents* / chemical synthesis
Antineoplastic Agents* / chemistry
Antineoplastic Agents* / pharmacology
Cell Line, Tumor
Cell Survival / drug effects
Drug Design*
Fungi / drug effects*
Humans
Hydrazones / chemical synthesis
Hydrazones / chemistry*
Hydrazones / pharmacology
Microbial Sensitivity Tests
Monosaccharides / chemistry*
Schiff Bases / chemistry

Substances

Antifungal Agents
Antineoplastic Agents
Hydrazones
Monosaccharides
Schiff Bases