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Vol. 36 No. 2 (2024): Vol 36 Issue 2, 2024

Copyright (c) 2024 RAMCHANDER JADAV

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Synthesis of New Quinoline based Morpholine-1,2,3-Triazole Hybrids and their Cytotoxicity

https://doi.org/10.14233/ajchem.2024.31238
Goli J. Rupa Sree
Department of Chemistry, University College of Science, Osmania University, Hyderabad-500007, India
https://orcid.org/0009-0003-6032-0073
Dharmasothu Veeranna
Department of Chemistry, University College of Science, Osmania University, Hyderabad-500007, India
https://orcid.org/0009-0005-9125-2135
J. Ramchander
Department of Chemistry, University College of Science, Osmania University, Hyderabad-500007, India
https://orcid.org/0000-0003-3472-2581

Corresponding Author(s) : J. Ramchander

ramorgchemou@gmail.com

Asian Journal of Chemistry, Vol. 36 No. 2 (2024): Vol 36 Issue 2, 2024

Abstract

Regioselective synthesis of a series of 1-aryl 1,2,3-triazoles-4-methoxy methyl-3-quinoline-2-morpholine employing click reaction is presented. Highly selective and efficient copper(I)-catalyzed 1,3-dipolar cycloaddition between 2-morpholinoquinoline-3-methyl propargyl ether and various aryl azides 5a-j yielded the title compounds 6a-j in 71% to 85%. The structure of all the novel 1,2,3-triazoles was characterized by 1H NMR, 13C NMR, IR and mass spectral analysis. The analogues were evaluated for their in vitro anticancer activity against MDA-MB-231 cell line. All the synthesized compounds were proven to have anticancer activity in comparison to reference drug doxorubicin. Especially, chloro and fluoro substituent compounds demonstrated potent activity with IC50 values of 17.20 ± 0.09 µM and 23.56 ± 0.09 µM, which proved their efficacy and could be further studied for the development of novel chemotherapeutics.

Keywords

2-Morpholinoquinoline-3-methylpropargyl ether Arylazides 1,3-Dipolar cycloaddition Regioselective
Sree, G. J. R., Veeranna, D., & Ramchander, J. (2024). Synthesis of New Quinoline based Morpholine-1,2,3-Triazole Hybrids and their Cytotoxicity. Asian Journal of Chemistry, 36(2), 516–520. https://doi.org/10.14233/ajchem.2024.31238
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