Synthesis And Bioactivities Of Phenyl-Azo Derivatives

Nocuous fungi were harmful to human’s health, and had some adverse effects in poultry, breed, agriculture and forestry. There were lots of antifugual drugs in our market, most of all had good effect of prevention and cure, but the fungi would form drug-resistance when those drugs were used long and long, and the effect of antifugui would decrease gradually, that’s the reason we had to search for novel and more fine antifugui drugs endlessly.Through earlier literatures surveying, we found that: phenol derivatives were used as antifugui drugs but substituted phenylazophenols are reported to use in antifugui area rarely. Although 8-hydroxyquinoline derivatives had wide bioactivity, 5,5′-diazophenyl-8-hydroxy- quinoline sulfonates are not reported to use as antifugui and anti-HIV drugs.So we used 8-hydroxyquinoline as starting material, designed and synthesized ten target compounds. Used substituted phenol as lead compound, designed and synthesized twenty three target compounds through coupling reaction.The experiment results were as follows:1. we used 8-hydroxyquinoline as starting material, synthesized ten target compounds, CA search proved all compounds were new compounds, and then identified them, determined those anti-HIV activity in vitro and anti-fungi activity of plant pathogenic fungi. The result showed that, compound 6e had better antifungal activity when the concentration was 0.05 mg/mL, and compound 6f, 6g, 6i had potential anti-HIV activity.2. Synthesized twenty three substituted phenylazophenols through coupling reaction, and compound 4v was new compound, used melt point, 1H-NMR, 13C-NMR to identify these structures, at the same time, we also determined those antifungal activity against Fusarium graminearum, Bipolaris sorokinianum, Fusarium oxysporium f. sp cucumarinum, Alternaria brassicae, Fusarium oxysporium f. sp. Vasinfectum, Pyricularia oryzae, Alternaria alternata seven plant pathogenic fungus. The result showed that, most of all had well anti-fungi activity especially compound 4a, 4b, 4f, 4n, 4q, 4u, 4v at 0.10 mg/mL, and had the best antifungi activity was 4b at 0.05 mg/mL;the result of EC50 showed that the best anti-fungi was 4u, and its value of EC50 against Fusarium oxysporium f. sp cucumerinum, Bipolaris sorokiniana and Alternaria alternata was 13.57, 8.54, 6.96μg/mL respectively. Substituted phenyl-azo phenols has well antifungi activity against plant pathogenic fungus, so it deserves to be studied furtherly.