苯并异噻唑啉酮酰胺衍生物的合成及其对柞蚕链球菌的抑菌活性评价  

Synthesis of Benzoisothiazolinone Amide Derivatives and Evaluation of Their Antibacterial Activity against Streptococcus Pernyi

作　　者：刘铁成 陈有嗣[1,2] 杨金琛 刘洪丽[1,2] 曾航 赫英姿[1,2] 王立石 牛雄雷 LIU Tie-cheng;CHEN You-si;YANG Jin-chen;LIU Hong-li;ZENG Hang;HE ying-zi;WANG Li-shi;NIU Xiong-lei(Sericultural Research Institute of Liaoning Province,Fengcheng,Liaoning 118100;Technology Innovation Center of Sericultural Chemicals,Liaoning Province,Fengcheng,Liaoning 118100)

机构地区：[1]辽宁省蚕业科学研究所,辽宁凤城118100 [2]辽宁省蚕药专业技术创新中心,辽宁凤城118100

出　　处：《辽宁农业科学》2021年第5期7-11,共5页Liaoning Agricultural Sciences

基　　金：现代农业产业技术体系建设专项(CARS-18);农业部辽宁野蚕科学观测实验站项目(23-S-15);辽宁省自然科学基金指导计划项目(20180551245);辽宁省野蚕研究重点实验室项目(2003)。

摘　　要：为了调变其疏水性并筛选出对柞蚕链球菌具有较高抑菌活性的化合物,以苯并异噻唑啉酮为母体结构进行了系列酰化衍生物的设计合成与结构表征,采用涂平板数菌落法和琼脂孔穴扩散法测定衍生物对柞蚕链球菌的离体抑菌活性,采用室内养蚕试验测定衍生物的活体抑菌活性。合成了取代基为烷基链酰胺衍生物6个和取代基为芳基酰胺衍生物5个,并采用熔点测试和1H-NMR测定确认了其结构。涂平板数菌落法结果表明,在处理浓度高于62.5 mg/L时,苯并异噻唑啉酮酰胺衍生物抑菌活性不亚于母体化合物;随着处理浓度降低苯并异噻唑啉酮酰胺衍生物抑菌活性呈降低趋势:在低处理浓度下(≤32.5 mg/L),仅部分衍生物可保留母体化合物的抑菌活性。琼脂孔穴扩散法结果表明,不同处理浓度时,衍生物的抑菌圈直径均小于相应浓度处理时的母体化合物,且低处理浓度(≤500 mg/L)表现更为显著。初步的活体试验表明,衍生物对柞蚕体内的柞蚕链球菌的抑菌活性较之母体化合物下降显著。这说明,苯并异噻唑啉酮酰胺化改造可能无助于提高其对柞蚕链球菌的抑菌活性。In order to modify their hydrophobicity and screen out compounds with high antibacterial activity against Streptococcus pernyi, a series of acylated derivatives were designed, synthesized 、and characterized with Benzoisothiazolinone(BIT) as the parent structure. The antibacterial activity of the derivatives against Streptococcus pernyi in vitro was determined by plate count colony method and agar hole diffusion method, and the antibacterial activity of the derivatives against Streptococcus pernyi in vivo was determined by indoor silkworm rearing. Six alkyl chain amide derivatives and five aryl amide derivatives were synthesized, and their structures were confirmed by melting point test and 1H-NMR. The results showed that the antibacterial activity of BIT amide derivatives was no less than that of BIT when the treatment concentration of BIT amide was higher than 62.5 mg/L;the antibacterial activity of BIT amide derivatives decreased with the decrease of the treatment concentration of BIT amide derivatives. Only some derivatives could retain the antibacterial activity of the parent compound at low concentration(≤ 32.5 mg/L). The results of agar hole diffusion method showed that the diameter of inhibition zone of the derivatives at different concentrations was smaller than that of BIT at corresponding treatment concentrations, and the effect of low concentration(≤ 500 mg/L) was more significant. Preliminary in vivo experiments showed that the antibacterial activity of the derivatives against Streptococcus pernyi in Tussah was significantly lower than that of the parent compound. These results suggest that the modification of BIT by acylation may not improve their antibacterial activity against Streptococcus pernyi.

关 键 词：苯并异噻唑啉酮 衍生物 合成 柞蚕链球菌 抑菌活性 

分 类 号：TQ252.5[化学工程—有机化工]