title: 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.
abstract: 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.
authors: Center for Research and Development of Fine Chemicals, Key Laboratory of Green Pesticide and Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, PR China.
authors: Cai-Jun
authors: CJ
authors: Chen
authors: Bao-An
authors: BA
authors: Song
authors: Song
authors: S
authors: Yang
authors: Guang-Fang
authors: GF
authors: Xu
authors: Pinaki S
authors: PS
authors: Bhadury
authors: Lin-Hong
authors: LH
authors: Jin
authors: De-Yu
authors: DY
authors: Hu
authors: Qian-Zhu
authors: QZ
authors: Li
authors: Fang
authors: F
authors: Liu
authors: Wei
authors: W
authors: Xue
authors: Ping
authors: P
authors: Lu
authors: Zhuo
authors: Z
authors: Chen
mesh_terms: 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*
chemical_list: 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