Novel benzimidazole derived naphthalimide triazoles: synthesis, antimicrobial activity and interactions with calf thymus DNA  

作　　者：Yun-Lei Luo Kishore Baathulaa Vijaya Kumar Kannekanti Cheng-He Zhou Gui-Xin Cai 

机构地区：[1]Key Laboratory of Applied Chemistry of Chongqing Municipality [2]Institute of Bioorganic & Medicinal Chemistry, School of Chemistry and Chemical Engineering, Southwest University [3]Department of Chemistry, Kakatiya University [4]Indian Institute of Chemical Technology

出　　处：《Science China Chemistry》2015年第3期483-494,共12页中国科学（化学英文版）

基　　金：supported by the National Natural Science Foundation of China(21172181,21372186,81450110094);the key program from Natural Science Foundation of Chongqing(CSTC2012jj B10026);the Specialized Research Fund for the Doctoral Program of Higher Education of China(SRFDP 20110182110007);the Doctoral Fund of Southwest University(SWU111075);the Research Funds for the Central Universities(XDJK2013C112);Chongqing Special Foundation for Postdoctoral Research Proposal(Xm201450)

摘　　要：A novel series of benzimidazole derived naphthalimide triazoles and some corresponding triazoliums have been successfully synthesized and characterized by 1H NMR, 13 C NMR, 1H-1H COSY, IR and HRMS spectra. All the new compounds were screened for their antimicrobial activities in vitro by two-fold serial dilution. 2-Chlorobenzyl triazolium 8g and compound 9b with octyl group exhibited the best antibacterial activities among all the tested compounds, especially against S. aureus with inhibitory concentration of 2 μg/mL which was equipotent potency to Norfloxacin(MIC=2 μg/mL) and more active than Chloromycin(MIC=7 μg/mL). Triazoliums 8g and 8f bearing 3-fluorobenzyl moiety displayed the best antifungal activities(MIC=2-19 μg/mL) against all the tested fungal strains without being toxic to PC12 cell line within concentration of 128 μg/m L. Further investigations by fluorescence and UV-Vis spectroscopic methods revealed that the compound 8g could effectively intercalate into calf thymus DNA to form the 8g-DNA complex which could block DNA replication, exerting powerful antimicrobial activities.A novel series of benzimidazole derived naphthalimide triazoles and some corresponding triazoliums have been successfully synthesized and characterized by 1H NMR, 13 C NMR, 1H-1H COSY, IR and HRMS spectra. All the new compounds were screened for their antimicrobial activities in vitro by two-fold serial dilution. 2-Chlorobenzyl triazolium 8g and compound 9b with octyl group exhibited the best antibacterial activities among all the tested compounds, especially against S. aureus with inhibitory concentration of 2 μg/mL which was equipotent potency to Norfloxacin（MIC=2 μg/mL） and more active than Chloromycin（MIC=7 μg/mL）. Triazoliums 8g and 8f bearing 3-fluorobenzyl moiety displayed the best antifungal activities（MIC=2-19 μg/mL） against all the tested fungal strains without being toxic to PC12 cell line within concentration of 128 μg/m L. Further investigations by fluorescence and UV-Vis spectroscopic methods revealed that the compound 8g could effectively intercalate into calf thymus DNA to form the 8g-DNA complex which could block DNA replication, exerting powerful antimicrobial activities.

关 键 词：NAPHTHALIMIDE BENZIMIDAZOLE TRIAZOLE ANTIBACTERIAL ANTIFUNGAL calf thymus DNA 

分 类 号：TQ463.5[化学工程—制药化工]