Microwave-assisted Catalyzed Synthesis and In vitro Bioactivity Evaluation of Benzimidazoles Bearing Phenolic Hydroxyl

doi:10.1007/s40242-020-0274-0

高等学校化学研究 ›› 2021, Vol. 37 ›› Issue (3): 639-646.doi: 10.1007/s40242-020-0274-0

Microwave-assisted Catalyzed Synthesis and In vitro Bioactivity Evaluation of Benzimidazoles Bearing Phenolic Hydroxyl

YAN Liuqing¹, FU Jiaxu¹, LI Shuang², ZHANG Jinlong¹, WANG Shuang¹, GU Qiang¹, ZHANG Yumin¹, LIN Feng²

1. College of Chemistry, Jilin University, Changchun 130012, P. R. China;
2. School of life Sciences, Jilin University, Changchun 130012, P. R. China

收稿日期:2020-08-29 修回日期:2020-10-19 出版日期:2021-06-01 发布日期:2020-10-28
通讯作者: ZHANG Yumin, LIN Feng E-mail:zhang_ym@jlu.edu.cn;linfeng@jlu.edu.cn
基金资助:
We are grateful to Dr. WANG Chunyu(Jilin University, China) for NMR spectra, Dr. WEI Zhonglin(Jilin University, China) for MS spectrum and Dr. CAO Jungang(Jilin University, China) for fluorescence spectra.

Microwave-assisted Catalyzed Synthesis and In vitro Bioactivity Evaluation of Benzimidazoles Bearing Phenolic Hydroxyl

YAN Liuqing¹, FU Jiaxu¹, LI Shuang², ZHANG Jinlong¹, WANG Shuang¹, GU Qiang¹, ZHANG Yumin¹, LIN Feng²

1. College of Chemistry, Jilin University, Changchun 130012, P. R. China;
2. School of life Sciences, Jilin University, Changchun 130012, P. R. China

Received:2020-08-29 Revised:2020-10-19 Online:2021-06-01 Published:2020-10-28
Contact: ZHANG Yumin, LIN Feng E-mail:zhang_ym@jlu.edu.cn;linfeng@jlu.edu.cn
Supported by:
We are grateful to Dr. WANG Chunyu(Jilin University, China) for NMR spectra, Dr. WEI Zhonglin(Jilin University, China) for MS spectrum and Dr. CAO Jungang(Jilin University, China) for fluorescence spectra.

摘要/Abstract

摘要： An efficient and facile method was introduced for the synthesis of benzimidazoles in this paper. The optimum reaction conditions were determined. A series of benzimidazoles bearing phenolic hydroxyl(2a-2t) were synthesized in moderate to excellent yields starting from differently substituted hydroxyl benzaldehyde and 4-position substituted o-phenylenediamine via nucleophilic addition in the presence of catalyst Na₂S₂O₅ under microwave irradiation condition. Herein, effects of the catalyst, molar ratio of reactants, reaction temperature and solvent were investigated. The optimal reaction condition was determined. The effect of DMF and EtOH solvent on the reaction was compared. The synthesized compounds were characterized by FTIR, HRMS, ¹H NMR and ¹³C NMR spectroscopy. Further, the bacteriostatic activities of the synthesized compounds were evaluated with ciprofloxacin and itraconazole as a positive control, respectively. Compounds 2b, 2n, 2q and 2r exhi-bited some antibacterial activity. The lowest MIC of antibacterial activity of compound 2b was 32 μg/mL. Meanwhile, the luminescence property of compound 2b was studied. The antibacterial activity of compound 2b, along with their good fluorescence performance highlighted the potential of these compounds as lead structures and owned fluorescence trace for further study towards the development of novel drugs and functional mechanisms in living organisms.

关键词: Benzimidazole, Microwave irradiation, Solvent effect, Antimicrobial activity, Luminescence property

Abstract: An efficient and facile method was introduced for the synthesis of benzimidazoles in this paper. The optimum reaction conditions were determined. A series of benzimidazoles bearing phenolic hydroxyl(2a-2t) were synthesized in moderate to excellent yields starting from differently substituted hydroxyl benzaldehyde and 4-position substituted o-phenylenediamine via nucleophilic addition in the presence of catalyst Na₂S₂O₅ under microwave irradiation condition. Herein, effects of the catalyst, molar ratio of reactants, reaction temperature and solvent were investigated. The optimal reaction condition was determined. The effect of DMF and EtOH solvent on the reaction was compared. The synthesized compounds were characterized by FTIR, HRMS, ¹H NMR and ¹³C NMR spectroscopy. Further, the bacteriostatic activities of the synthesized compounds were evaluated with ciprofloxacin and itraconazole as a positive control, respectively. Compounds 2b, 2n, 2q and 2r exhi-bited some antibacterial activity. The lowest MIC of antibacterial activity of compound 2b was 32 μg/mL. Meanwhile, the luminescence property of compound 2b was studied. The antibacterial activity of compound 2b, along with their good fluorescence performance highlighted the potential of these compounds as lead structures and owned fluorescence trace for further study towards the development of novel drugs and functional mechanisms in living organisms.

Key words: Benzimidazole, Microwave irradiation, Solvent effect, Antimicrobial activity, Luminescence property

YAN Liuqing, FU Jiaxu, LI Shuang, ZHANG Jinlong, WANG Shuang, GU Qiang, ZHANG Yumin, LIN Feng. Microwave-assisted Catalyzed Synthesis and In vitro Bioactivity Evaluation of Benzimidazoles Bearing Phenolic Hydroxyl[J]. 高等学校化学研究, 2021, 37(3): 639-646.

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Microwave-assisted Catalyzed Synthesis and In vitro Bioactivity Evaluation of Benzimidazoles Bearing Phenolic Hydroxyl

Microwave-assisted Catalyzed Synthesis and In vitro Bioactivity Evaluation of Benzimidazoles Bearing Phenolic Hydroxyl

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