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Synthesis and biological activity of 3,6-diaryl-7H-thiazolo[3,2-b][1,2,4]triazin-7-one derivatives as novel acetylcholinesterase inhibitors

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Abstract

Acetylcholinesterase inhibitors played significant roles in treatment of Alzheimer’s disease. Based on the research foundation of our previous work and molecular modeling, twelve 3,6-diaryl-7H-thiazolo[3,2-b][1,2,4]triazin-7-one derivatives were synthesized and characterized by mass spectra, infrared spectra, NMR and elemental analyses. The study of AChE inhibitory activity was carried out using the Ellman colorimetric assay with huperzine-A as the positive control. All target compounds exhibited more than 40% inhibition at 10 μM. Some target compounds showed good inhibition against AChE. The preliminary structure-activity relationships were the halogen atoms at the phenyl ring at the C6 position, the hydroxy groups and the long side chains at the phenyl ring at the C3 position of the parent nucleus played significant roles in the AChE inhibitory activity of the target compounds.

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Authors and Affiliations

  1. Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education; Department of Organic Chemistry, School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang, 110016, China

    Zhe Jin, Liu Yang, HeNan Xu, ErFang Huang & Chun Hu

  2. Department of Biochemistry, Chinese University of Hong Kong, Hong Kong SAR, China

    David ChiCheong Wan, Shuo Li & HuangQuan Lin

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  1. Zhe Jin
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  2. Liu Yang
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  3. HeNan Xu
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  4. ErFang Huang
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  5. David ChiCheong Wan
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  6. Shuo Li
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  7. HuangQuan Lin
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  8. Chun Hu
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Correspondence to Chun Hu.

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Jin, Z., Yang, L., Xu, H. et al. Synthesis and biological activity of 3,6-diaryl-7H-thiazolo[3,2-b][1,2,4]triazin-7-one derivatives as novel acetylcholinesterase inhibitors. Sci. China Chem. 53, 2297–2303 (2010). https://doi.org/10.1007/s11426-010-4094-9

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  • DOI: https://doi.org/10.1007/s11426-010-4094-9

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