Synthesis of novel 2-phenylsulfonylhydrazono-3-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyl)thiazolidine-4-ones from thiosemicarbazide precursors

被引:21
|
作者
Li, Yu Xin [1 ]
Wang, Su Hua [1 ]
Li, Zheng Ming [1 ]
Su, Na [1 ]
Zhao, Wei Guang [1 ]
机构
[1] Nankai Univ, State Key Lab Elementoorgan Chem, Tianjin 300071, Peoples R China
基金
中国国家自然科学基金;
关键词
thiosemicarbazide; thiazolidine-4-one; fungicide;
D O I
10.1016/j.carres.2006.09.010
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
To develop novel biologically active organic compounds possessing a sugar moiety, a series of 2-phenylsulfonylhydrazono-3-(2',3',4',6'-tetra-O-acetyl-beta-D-glueopyranosyl)thiazolidine-4-one were synthesized via reaction of the thiosemicarbazide with ethyl bromoacetate. Their chemical structures were characterized by H-1 and C-13 NMR spectroscopy, elemental analysis and MS. The bioassay results indicated that some of these compound exhibit moderate fungicidal and herbicidal activities. Furthermore, the effect of various solvents at reflux temperature on the reactions of ethyl bromoacetate with the related thiosemicarbazides was investigated. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2867 / 2870
页数:4
相关论文
共 50 条
  • [2] Synthesis and Biological Activity of Novel 2,3-Dihydro-2-phenylsulfonylhydrazono-3-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyl)thiazoles
    Wang Hao-an
    Li Yu-xin
    Li Zheng-ming
    Cheng Hai-ying
    Wang Su-hua
    Liu Bin
    [J]. CHEMICAL RESEARCH IN CHINESE UNIVERSITIES, 2009, 25 (01) : 52 - 55
  • [3] 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl azide
    Temelkoff, DP
    Norris, P
    Zeller, M
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2004, 60 : O1975 - O1976
  • [4] 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl azide
    Dedola, Simone
    Nepogodiev, Sergey A.
    Hughes, David L.
    Field, Robert A.
    [J]. ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 2008, 64 : O445 - O446
  • [5] Reaction of N-alkylisatins with 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiosemicarbazide
    Nguyen Dinh Thanh
    Nguyen Thi Kim Giang
    [J]. JOURNAL OF CHEMISTRY, 2013, 2013
  • [6] 2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl disulfide tetrahydrofuran solvate
    Brito, Ivan
    Szilagyi, Laszlo
    Lopez-Rodriguez, Matias
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2008, 64 : O2472 - U3631
  • [8] 4-Methoxybenzaidehyde 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)thiosemicarbazone
    Zhang, SS
    Yang, B
    Li, JZ
    Liu, Q
    Li, XM
    Jiao, K
    Kassim, M
    Yamin, BM
    [J]. ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2004, 60 : O2050 - O2052
  • [9] Solid-state structure of methyl 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-galactopyranoside and methyl 3,4,6-tri-O-acetyl-2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-galactopyranoside
    Gubica, Tomasz
    Bukowicki, Jaroslaw
    Stepien, Dorota K.
    Ostrowski, Andrzej
    Pisklak, Dariusz M.
    Cyranski, Michal K.
    [J]. JOURNAL OF MOLECULAR STRUCTURE, 2013, 1037 : 49 - 56
  • [10] Microwave-Assisted Synthesis of Novel Tetra-O-acetyl-β-D-glucopyranosyl Thiosemicarbazones of Substituted Isatins
    Thanh, Nguyen D.
    Giang, Nguyen T. K.
    [J]. LETTERS IN ORGANIC CHEMISTRY, 2011, 8 (07) : 500 - 503