Triazolbenzo[d]thiazoles: Efficient synthesis and biological evaluation as neuroprotective agents

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Abstract

A number of (1H-1,2,3-triazol-1-yl)benzo[d]thiazoles were synthesized utilizing a versatile Cu-catalyzed azide–alkyne click reaction (CuAAC) on tautomeric benzo[4,5]thiazolo[3,2-d]tetrazole (1) and 2-azidobenzo[d]thiazole (2) starting materials. Moreover, one of the resulting products of this investigation, triazolbenzo[d]thiazole 22, was found to possess significant neuroprotective activity in human neuroblastoma (SH-SY5Y) cells.

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Acknowledgments

Financial support was provided by the National Science Foundation (CHE-0910870, CHE-0449845) and the National Institutes of Health (GM089153). B.A. thanks the Bristol-Myers Squibb Graduate Chemist Fellowship and Alfred P. Sloan Minority Ph.D. Program for fellowship support. We also thank Mr. Michael Donald and Mr. Wayne Conrad (UC Davis Department of Chemistry) for synthetic assistance, and Mr. Parrin Patterson (LSU Health Sciences Center) for assistance with bioassays.

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