Synthesis and antifungal activity of novel sulfoxide derivatives containing trimethoxyphenyl substituted 1,3,4-thiadiazole and 1,3,4-oxadiazole moiety

被引:170
作者
Liu, Fang [1 ]
Luo, Xiao-Qiong [1 ]
Song, Bao-An [1 ]
Bhadury, Pinaki S. [1 ]
Yang, Song [1 ]
Jin, Lin-Hong [1 ]
Xue, Wei [1 ]
Hu, De-Yu [1 ]
机构
[1] Guizhou Univ, Minist Educ, Ctr Res & Dev Fine Chem, Key Lab Green Pesticide & Bioengn, Guiyang 550025, Peoples R China
基金
中国国家自然科学基金;
关键词
sulfoxides; thioether; antifungal bioactivity; mechanism of action;
D O I
10.1016/j.bmc.2008.02.006
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
Selective oxidation of sulfides 7 or 8 to sulfoxides 9 or 10 is achieved by mCPBA. The structures of the compounds 9 or 10 are confirmed by elemental analysis, IR, and H-1 NMR. The bioassay results showed that title compound 10a possess high antifungal activities with EC50 values ranging from 19.91 to 63.97 mu g/mL. The mechanism of action of 10a against Sclerotinia sclerotiorum was studied. After treating with compound 10a at 100 mu g/mL for 12 h, the mycelial reducing sugar, D-GlcNAc, soluble protein and pyruvate content, chitinase activity showed declining tendency. (C) 2008 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3632 / 3640
页数:9
相关论文
共 25 条
[1]   Antimycotic activities of selected plant flora, growing wild in Lebanon, against phytopathogenic fungi [J].
Abou-Jawdah, Y ;
Sobh, H ;
Salameh, A .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2002, 50 (11) :3208-3213
[3]  
ANTONIO R, 1992, J BACTERIOL, V174, P3450
[4]   Phenylpyrazole insecticide photochemistry, metabolism, and GABAergic action: Ethiprole compared with fipronil [J].
Caboni, P ;
Sammelson, RE ;
Casida, JE .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2003, 51 (24) :7055-7061
[5]   Antifungal activity of 4-methyl-6-alkyl-2H-pyran-2-ones [J].
Chattapadhyay, TK ;
Dureja, P .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2006, 54 (06) :2129-2133
[6]   Synthesis and antifungal activities of 5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-thiadiazole and 5(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-oxadiazole derivatives [J].
Chen, Cai-Jun ;
Song, Bao-An ;
Yang, Song ;
Xu, Guang-Fang ;
Bhadury, Pinaki S. ;
Jin, Lin-Hong ;
Hu, De-Yu ;
Li, Qian-Zhu ;
Liu, Fang ;
Xue, Wei ;
Lu, Ping ;
Chen, Zhuo .
BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (12) :3981-3989
[7]  
CHICH D, 2002, TETRAHEDRON, V58, P3865
[8]   CHEMICAL-PROPERTIES AND ANTITUMOR-ACTIVITY OF COMPLEXES OF PLATINUM CONTAINING SUBSTITUTED SULFOXIDES [PTCL(R'R''SO)(DIAMINE)]NO3 - CHIRALITY AND LEAVING-GROUP ABILITY OF SULFOXIDE AFFECTING BIOLOGICAL-ACTIVITY [J].
FARRELL, N ;
KILEY, DM ;
SCHMIDT, W ;
HACKER, MP .
INORGANIC CHEMISTRY, 1990, 29 (03) :397-403
[9]   Synthesis of fenthion sulfoxide and fenoxon sulfoxide enantiomers: Effect of sulfur chirality on acetylcholinesterase activity [J].
Gadepalli, Rama Sarma V. S. ;
Rimoldi, John M. ;
Fronczek, Frank R. ;
Nillos, Mae ;
Gan, Jay ;
Deng, Xin ;
Rodriguez-Fuentes, Gabriela ;
Schlenk, Daniel .
CHEMICAL RESEARCH IN TOXICOLOGY, 2007, 20 (02) :257-262
[10]   Solid state NMR for determination of degree of acetylation of chitin and chitosan [J].
Heux, L ;
Brugnerotto, J ;
Desbrières, J ;
Versali, MF ;
Rinaudo, M .
BIOMACROMOLECULES, 2000, 1 (04) :746-751