Synthesis Of Heterocyclic Thioethers & Study On Their Complexes And Biological Activities

Sixteen compounds of imidazol and tetrazole derivatives, 4-[(1-methyl-1H-imidazol-2-ylthio)methyl]pyridine(MYPD), 2,2'-[(but-2-ene-1,4-diyl)bisthio]bis (1 -methyl-1 H-imidazol)(BMBE), 1,4-bis[( 1 -methyl-1H-imidazol-2-ylthio)methyl] benzene(BMBZ), S,S'-bis( 1 -methyl-1H-imidazol-2-ylthio)benzene-1,4-bis(carbo thioate)(BMCT), 2,3-bis[(1-methyl-1H-imidazol-2-ylthio)methyl]quinoxaline (BMQL), 1,3,5-tris[( 1-methyl-1H-imidazole-2-ylthio)methyl]benzene(TMB), 2,4,6-trimethyl-1,3,5-tris[(1-methyl-1H-imidazole-2-ylthio)methyl]benzene(TEB), 4-[(1 -phenyl-1H-tetrazol-5-ylthio)methyl]pyridine(TMPD), S,S'-bis( 1-phenyl-1H-tetrazol-5-ylthio)benzene-1,4-bis(carbothioate)(BTCT), 2,3-bis[(1-phenyl-1H-tetrazol-5-ylthio)methyl]quinoxaline(BTQL), 1,3,5-tris[(1-phenyl-1H-tetrazol-5-ylthio)methyl]benzene(TTB), 5-[2-( 1 -methyl-1H-imidazol-2-ylthio)ethylthio]-1 -phenyl-1H-tetrazole(TBTM), 5-[4-( 1-methyl-1H-imidazol-2-ylthio)but-2-enylthio]-1 -phenyl-1H-tetrazole(TBEM), 5-{4-[(1-methyl-1H-imidazol-2-ylthio)methyl] Benzylthio}-1 -phenyl-1H-tetrazole(THBM),5-{2-[2-(1-methyl-1H-imidazol-2-ylthio)ethoxy]ethylthio}-1 -phenyl-1H-tetrazole(TEOM) and 5-{2-{2-[2-(1-methyl-1H-imidazol-2-ylthio)ethoxy]ethoxy}ethylthio}-1 -phenyl-1H-tetrazole(TDOM) were synthesized with the reaction of thioimidazole, thiotetrazole and varied bromides by nucleophilic reaction. All of the compounds were determinded by IR, ¹H NMR, ¹³H NMR and element analysis. X-ray diffraction gave the structures of BMBZ, BMQL, BTQL, TTB and revealed that BMBZ is centrosymmetric and there is interaction between the two sulfur atoms among the molecules.The four crystals of coordination complexes, {[Ag(TEB)](NO₃)}_{∞}, {(Co(TEB)(NO₃)] (NO₃)}_{∞}, {[Cd(TEB)(H₂O)](ClO₄)₂}_{∞}and {[Co(BMQL)(NO₃)₂]}_{∞}were obtained by the diffusion method, and their structures were determined by IR and X-ray diffraction. In the three complexes that composed of the TEB, the coordination conformation of TEB is resemble. We also found that BTQL and TEB poss the bioactivity of inhibiting lung cancer.