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.
Starting from the key intermediate 5-(3,4,5-trimethoxyphenyl)-1,3,4-thiadiazole-2-thiol (4) or the oxadiazole analogue (5), the title compounds 9 and 10 are synthesized by a two-step process. Thioetherification reaction of 4 or 5 with an organic halide catalyzed by indium or indium tribromide first affords appropriate sulfide 7 or 8, which is then converted into title compounds 9 or 10 by hydrogen peroxide oxidation catalyzed by ammonium molybdate in ionic liquid [bmim]PF6. The structures are unequivocally confirmed by spectroscopic (IR, 1H and 13C NMR) data and elemental analyses. The structures of 8d and 10q are further established by X-ray crystallographic diffraction analysis. The compounds have been shown to be fungicidally active. Title compounds 10i and 10j can inhibit mycelia growth by approximately 50% (EC50) at 2.9-93.3 microg/mL in vitro against 10 kinds of fungi.
Chen
Cai-Jun
CJ
Center for Research and Development of Fine Chemicals, Key Laboratory of Green Pesticide and Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, PR China.
Song
Bao-An
BA
Yang
Song
S
Xu
Guang-Fang
GF
Bhadury
Pinaki S
PS
Jin
Lin-Hong
LH
Hu
De-Yu
DY
Li
Qian-Zhu
QZ
Liu
Fang
F
Xue
Wei
W
Lu
Ping
P
Chen
Zhuo
Z
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D005658:Fungi / Q000145:classification / Q000187:drug effects; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008958:Models, Molecular; D010069:Oxadiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013055:Spectrophotometry, Infrared; D013830:Thiadiazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
C521466:5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-oxadiazole; C521467:5-(3,4,5-trimethoxyphenyl)-2-sulfonyl-1,3,4-thiadiazole; D000935:Antifungal Agents; D010069:Oxadiazoles; D013830:Thiadiazoles