含α,β-不饱和羰基结构化合物的定量结构-活性关系研究

Study on Quantitative Structure-Activity Relationship of Preservatives Containing α,β-Unsaturated Carbonyl Group

计算表征含α,β-不饱和羰基结构系列化合物的8个分子连接性指数和5个量子化学参数,用遗传算法对参数进行了优化筛选,获得了含α,β-不饱和羰基结构系列化合物的定量结构与抑制大肠杆菌的最低抑菌浓度(MIC)和抗菌半衰期(t0.5)间的关系模型。结果表明:与最低抑菌浓度显著相关的变量是最高占有轨道能量、最低空轨道能量与最高占有轨道能量差、3阶簇指数、4阶路径/簇指数,而且最高前沿占有轨道能量和4阶路径/簇指数对lg1/MIC均有正的贡献,而前沿轨道能差和3阶簇指数对抗菌作用强度有微小的负贡献;和半衰期显著相关的变量是最低空轨道能量、最低空轨道能量与最高占有轨道能量差、5阶路径指数、和4阶路径/簇指数,而且抗菌半衰期随5阶路径指数、4阶路径/簇指数以及最低空轨道能量与最高占有轨道能量差的增大而增大,而随最低空轨道能量的增加而减小。

Both molecular structure and electron action influence the antimicrobial activities of preservatives. For improving the research and development efficiency, the relationships between molecular structure of preservatives and activities including minimum inhibition concentration （MIC） and half life （t0.9 of inhibiting Escherichia coli were studied after some parameters including 8 molecular connectivity indexes and 5 quantum chemistry parameters of 19 preservatives containing α,β--unsaturated carbonyl group were calculated and optimizationally selected by genetic algorithm. Then, the equations of quantitative structure activity relationship were obtained by SPSS software. The equation of MIC showed that MIC is significantly correlated with the third order cluster index 3 Xpcv, the fourth order path-cluster index 4 Xpc^v, the energy of the highest occupied molecular orbital EHOMO as well as the energy difference AE of the highest occupied molecular orbital and the lowest unoccupied molecular orbital. The intension of anti-microbial actions of preservatives increase with increases of 4 xpc^v and EBOMO, but decrease with increases of 3 xv and A E. The equation of half life showed that t0.5 is significantly correlated with the fourth order path-cluster index 4 v xpc, the fifth order path index 5xp^v energy of the lowest unoccupied molecular orbital ELUMO, as well as the energy difference △E of the highest occupied molecular orbital and the lowest unoccupied molecular orbital. The anti-metabolic capabilities of preservatives increase with increases of 4xpcv, 5 x pcv and △E, but decrease with increase of EUMO.