Click chemistry inspired one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles and their Src kinase inhibitory activity

doi:10.1016/j.bmcl.2010.10.121

Bioorganic & Medicinal Chemistry Letters

Volume 21, Issue 1, 1 January 2011, Pages 449-452

https://doi.org/10.1016/j.bmcl.2010.10.121 Get rights and content

Abstract

Two classes of 1,4-disubstituted 1,2,3-triazoles were synthesized using one-pot reaction of α-tosyloxy ketones/α-halo ketones, sodium azide, and terminal alkynes in the presence of aq PEG (1:1, v/v) using the click chemistry approach and evaluated for Src kinase inhibitory activity. Structure–activity relationship analysis demonstrated that insertion of C₆H₅– and 4-CH₃C₆H₄– at position 4 for both classes and less bulkier aromatic group at position 1 in class 1 contribute critically to the modest Src inhibition activity (IC₅₀ = 32–43 μM) of 1,4-disubstituted 1,2,3-triazoles.

Graphical abstract

The synthesis and Src kinase inhibitory activity of two classes of 1,4-disubstituted 1,2,3-triazoles are reported.

Section snippets

Acknowledgments

We thank University Grants Commission (SAP, DRS), Birla Institute of Technology & Science, Pilani, India National Science Foundation, Grant # CHE 0748555, and the American Cancer Society Grant # RSG-07-290-01-CDD for the financial support.

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Click chemistry inspired one-pot synthesis of 1,4-disubstituted 1,2,3-triazoles and their Src kinase inhibitory activity

Abstract

Graphical abstract

Section snippets

Acknowledgments

Bioorg. Med. Chem.

Bioorg. Med. Chem. Lett.

Bioorg. Med. Chem. Lett.

Bioorg. Med. Chem. Lett.

Mol. Cancer Ther.

Mol. Cell

Struct. Fold Des.

ChemMedChem

J. Med. Chem.

Farmaco

Antimicrob. Agents Chemother.

J. Med. Chem.

New J. Chem.

Org. Biomol. Chem.