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Abstract

Introduction

Benzoxazole is a privileged scaffold with diverse biological activities, and its hybridization with a 1,2,3-triazole ring can improve affinity and efficacy. This study aimed to synthesize novel 1,2,3-triazole derivatives of 2-aminobenzoxazole and 2-mercaptobenzoxazole, and to evaluate their antiproliferative activity, predicted pharmacokinetic properties, and molecular interactions with kinase targets.

Methods

1,2,3-triazole derivatives of 2-aminobenzoxazole and 2-mercaptobenzoxazole were synthesized cyclization, propargylation, and copper-catalyzed click reaction. Antiproliferative activity was evaluated against human cancer cell lines: LN-229, Capan-1, HCT-116, NCI-H460, DND-41, HL-60, K-562, and Z-138. The ADME properties of 1,2,3-triazole-benzoxazole hybrids were evaluated using the SwissADME tool. The most active compounds were assessed for Human Gastrointestinal Absorption (HGA) and Blood-Brain Barrier (BBB) permeability using the Egan model. Molecular docking was performed on serine/threonine kinase TAO2 and tyrosine kinase c-Src.

Results

A series of novel 1,2,3-triazole derivatives of 2-amino and 2-mercaptobenzoxazole were synthesized click chemistry. Coumarin-containing compounds and showed the most pronounced antiproliferative activity across all tested cell lines. Both demonstrated high predicted HGA and low likelihood of crossing the BBB. Compound exhibited the highest binding affinity for TAO2, while compound showed strong interaction with c-Src.

Discussion

The results highlight the favorable influence of coumarin substitution on antiproliferative activity, with computational ADME and docking data supporting the observed efficacy.

Conclusion

This study outlines a viable method for the synthesis of novel 1,2,3-triazole derivatives of 2-aminobenzoxazole and 2-mercaptobenzoxazole. Compounds and demonstrate promising antiproliferative activity and pharmacokinetic potential, supporting their further development as anticancer candidates.

© 2025 The Author(s). Published by Bentham Science Publishers.
This is an open access article published under CC BY 4.0 https://creativecommons.org/licenses/by/4.0/legalcode.
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2025-07-31
2025-11-04

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Synthesis, Antiproliferative Activity, ADME Profiling, and Docking Studies of Novel 1, 2, 3-Triazole Derivatives of 2-Amino and 2-Mercaptobenzoxazole
Bentham Science Publishers ; https://doi.org/10.2174/0109298673393777250714045359
/content/journals/cmc/10.2174/0109298673393777250714045359
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  • Article Type:     Research Article
Keywords: 1,2,3-triazole ; molecular docking ; antitumor activity ; click chemistry ; benzoxazole ; CuAAC reaction

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