Design and Synthesis of New 5-aryl-4-Arylethynyl-1 H-1,2,3-triazoles with Valuable Photophysical and Biological Properties

Mariia M Efremova; Anastasia I Govdi; Valeria V Frolova; Andrey M Rumyantsev; Irina A Balova

doi:10.3390/molecules26092801

Design and Synthesis of New 5-aryl-4-Arylethynyl-1 H-1,2,3-triazoles with Valuable Photophysical and Biological Properties

Molecules. 2021 May 10;26(9):2801. doi: 10.3390/molecules26092801.

Authors

Mariia M Efremova¹, Anastasia I Govdi¹, Valeria V Frolova², Andrey M Rumyantsev³, Irina A Balova¹

Affiliations

¹ Institute of Chemistry, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, 199034 Saint Petersburg, Russia.
² Department of Pharmaceutical Chemistry, Saint Petersburg State Chemical Pharmaceutical University (SPCPU), 14A Professor Popov Str., 197376 Saint Petersburg, Russia.
³ Department of Genetics and Biotechnology, Saint Petersburg State University (SPbU), Universitetskaya nab. 7/9, 199034 Saint Petersburg, Russia.

Abstract

Cu-catalyzed 1,3-dipolar cycloaddition of methyl 2-azidoacetate to iodobuta-1,3-diynes and subsequent Suzuki-Miyaura cross-coupling were used to synthesize new triazoles derivatives: 5-aryl-4-arylethynyl-1H-1,2,3-triazoles. Investigation of their optical properties by using UV absorption and fluorescence emission spectroscopies revealed that all molecules possess fluorescence properties with the values of the Stokes shift more than 100 nm. The photophysical behavior of the two most promising triazoles in polar and non-polar solvents was also studied.

Keywords: 1,2,3-triazoles; 1,3-diynes; Suzuki-Miyaura cross-coupling; antimicrobial activity; azide–alkyne cycloaddition; cytotoxity; fluorescence; solvatochromism.

MeSH terms

HEK293 Cells
HeLa Cells
Humans
Light*
Molecular Conformation
Physical Phenomena*
Solvents
Spectrometry, Fluorescence
Triazoles / chemical synthesis*
Triazoles / chemistry
Triazoles / pharmacology*

Substances

Solvents
Triazoles

Grants and funding

19-73-10077/Russian Science Foundation