Synthesis and antifungal activity of novel sulfoxide derivatives containing trimethoxyphenyl substituted 1,3,4-thiadiazole and 1,3,4-oxadiazole moiety.
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 (1)H NMR. The bioassay results showed that title compound 10a possess high antifungal activities with EC(50) values ranging from 19.91 to 63.97 microg/mL. The mechanism of action of 10a against Sclerotinia sclerotiorum was studied. After treating with compound 10a at 100 microg/mL for 12 h, the mycelial reducing sugar, D-GlcNAc, soluble protein and pyruvate content, chitinase activity showed declining tendency.
Liu
Fang
F
Center for Research and Development of Fine Chemicals, Key Laboratory of Green Pesticide and Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, PR China.
Luo
Xiao-Qiong
XQ
Song
Bao-An
BA
Bhadury
Pinaki S
PS
Yang
Song
S
Jin
Lin-Hong
LH
Xue
Wei
W
Hu
De-Yu
DY
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001203:Ascomycota / Q000187:drug effects; D015394:Molecular Structure; D010069:Oxadiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D010084:Oxidation-Reduction; D012451:Safrole / Q000031:analogs & derivatives* / Q000737:chemistry; D013329:Structure-Activity Relationship; D013440:Sulfides / Q000737:chemistry; D013830:Thiadiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
D000935:Antifungal Agents; D010069:Oxadiazoles; D013440:Sulfides; D013830:Thiadiazoles; D012451:Safrole; C005746:sulfoxide