含吡啶环酰基硫脲的合成与杀菌活性

以芳基甲酰氯为原料,通过与硫氰酸钾反应生成芳酰基异硫氰酸酯,再与2-氨基吡啶或3-氨甲基吡啶进行加成反应,合成8种新型含吡啶环的酰基硫脲化合物:N-苯甲酰基-N'-α-吡啶基硫脲(Ⅲ1)、N-对硝基苯甲酰基-N'-α-吡啶基硫脲(Ⅲ2)、N-对氯苯甲酰基-N'-α-吡啶基硫脲(Ⅲ3)、N-邻甲氧基苯甲酰基-N'-α-吡啶基硫脲(Ⅲ4)、N-苯甲酰基-N'-β-吡啶甲基硫脲(Ⅳ1)、N-对硝基苯甲酰基-N'-β-吡啶甲基硫脲(Ⅳ2)、N-对氯苯甲酰基-N'-β-吡啶甲基硫脲(Ⅳ3)、N-邻甲氧基苯甲酰基-N'-β-吡啶甲基硫脲(Ⅳ4),收率分别为67.3%、36.4%、62.6%、83.5%、50.6%、37.8%、89.5%和66.2%.产物的结构经元素分析、红外光谱和核磁共振氢谱表征,并对目标化合物进行了杀菌活性测试,初步的测试结果表明,化合物Ⅲ对大肠杆菌有较强的抑制作用,对枯草杆菌无明显的抑制作用,而化合物Ⅳ的抑制作用与化合物Ⅲ相反,对枯草杆菌有较强的抑制作用,对大肠杆菌无明显的抑制作用.

Synthesis and bactericidal activities of thiourea derivatives containing pyridine ring

Aroyl isothiocyanate was obtained via the reaction of aroyl chloride with potassium isothiocyanate.Eight thiourea derivatives containing pyridine ring,including N-benzoyl-N＇-α-pyridyl thiourea（ Ⅲ1）,N-p-nitrobenzoyl-N＇-α-pyridyl thiourea（ Ⅲ2）,N-p-chlorobenzoyl-N＇-α-pyridyl thiourea（ Ⅲ3）,N-o-methoxybenzoyl-N＇-α-pyridyl thiourea（ Ⅲ4）,N-benzoyl-N＇-β-pyridyl methyl thiourea（ Ⅳ1）,N-p-nitrobenzoyl-N＇-β-pyridylmethyl thiourea（ Ⅳ2）,N-p-chlorobenzoyl-N＇-β-pyridyl methyl thiourea（ Ⅳ3） and N-o-methoxybenzoyl-N＇-β-pyridylmethyl thiourea（ Ⅳ4）,were synthesized by addition reaction of aroyl isothiocyanates with 2-amino-pyridine or 3-aminomethyl pyridine,in the yield of 67. 3%,36. 4%,62. 6%,83. 5%,50. 6%,37. 8%,89. 5% and 66.2% respectively. The structures of the products were characterized by1H NMR,IR and elemental analysis. The preliminary biological activity test indicated that the Ⅲ compounds had antibacterial activity against E. coli and had no obvious inhibition activity against B. subtilis. On the contrary,the Ⅳ compounds had antibacterial activity against B. subtilis and had no obvious inhibition activity against E. coli.