Design, Synthesis, Spectroscopic Characterisation and In Vitro Cytostatic Evaluation of Novel Bis(coumarin-1,2,3-triazolyl)benzenes and Hybrid Coumarin-1,2,3-triazolyl-aryl Derivatives
In this work, a series of novel 1,2,3-triazolyl-coumarin hybrid systems were designed as potential antitumour agents. The structural modification of the coumarin ring was carried out by Cu(I)-catalysed Huisgen 1,3-dipolar cycloaddition of 7-azido-4-methylcoumarin and terminal aromatic alkynes to obt...
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MDPI AG
2022-01-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/27/3/637 |
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| author | Kristina Pršir Ema Horak Marijeta Kralj Lidija Uzelac Sandra Liekens Ivana Murković Steinberg Svjetlana Krištafor |
| author_facet | Kristina Pršir Ema Horak Marijeta Kralj Lidija Uzelac Sandra Liekens Ivana Murković Steinberg Svjetlana Krištafor |
| author_sort | Kristina Pršir |
| collection | DOAJ |
| description | In this work, a series of novel 1,2,3-triazolyl-coumarin hybrid systems were designed as potential antitumour agents. The structural modification of the coumarin ring was carried out by Cu(I)-catalysed Huisgen 1,3-dipolar cycloaddition of 7-azido-4-methylcoumarin and terminal aromatic alkynes to obtain 1,4-disubstituted 1,2,3-triazolyl-coumarin conjugates <b>2a</b>–<b>g</b>, bis(1,2,3-triazolyl-coumarin)benzenes <b>2h</b>–<b>i</b> and coumarin-1,2,3-triazolyl-benzazole hybrids <b>4a</b>–<b>b</b>. The newly synthesised hybrid molecules were investigated for in vitro antitumour activity against five human cancer cell lines, colon carcinoma HCT116, breast carcinoma MCF-7, lung carcinoma H 460, human T-lymphocyte cells CEM, cervix carcinoma cells HeLa, as well as human dermal microvascular endothelial cells (HMEC-1). Most of these compounds showed moderate to pronounced cytotoxic activity, especially towards MCF-7 cell lines with IC<sub>50</sub> = 0.3–32 μM. In addition, compounds <b>2a</b>–<b>i</b> and <b>4a</b>–<b>b</b> were studied by UV-Vis absorption and fluorescence spectroscopy and their basic photophysical parameters were determined. |
| first_indexed | 2024-03-09T23:30:41Z |
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| id | doaj.art-dbc9f4316faf4a599a67e4313d61a02c |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-09T23:30:41Z |
| publishDate | 2022-01-01 |
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| record_format | Article |
| series | Molecules |
| spelling | doaj.art-dbc9f4316faf4a599a67e4313d61a02c2023-11-23T17:10:02ZengMDPI AGMolecules1420-30492022-01-0127363710.3390/molecules27030637Design, Synthesis, Spectroscopic Characterisation and In Vitro Cytostatic Evaluation of Novel Bis(coumarin-1,2,3-triazolyl)benzenes and Hybrid Coumarin-1,2,3-triazolyl-aryl DerivativesKristina Pršir0Ema Horak1Marijeta Kralj2Lidija Uzelac3Sandra Liekens4Ivana Murković Steinberg5Svjetlana Krištafor6Department of General and Inorganic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 19, 10000 Zagreb, CroatiaDepartment of General and Inorganic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 19, 10000 Zagreb, CroatiaDivision of Molecular Medicine, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, CroatiaDivision of Molecular Medicine, Ruđer Bošković Institute, Bijenička cesta 54, 10000 Zagreb, CroatiaLaboratory of Virology and Chemotherapy, Department of Microbiology and Immunology, Rega Institute for Medical Research, KU Leuven, 3000 Leuven, BelgiumDepartment of General and Inorganic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 19, 10000 Zagreb, CroatiaDepartment of General and Inorganic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 19, 10000 Zagreb, CroatiaIn this work, a series of novel 1,2,3-triazolyl-coumarin hybrid systems were designed as potential antitumour agents. The structural modification of the coumarin ring was carried out by Cu(I)-catalysed Huisgen 1,3-dipolar cycloaddition of 7-azido-4-methylcoumarin and terminal aromatic alkynes to obtain 1,4-disubstituted 1,2,3-triazolyl-coumarin conjugates <b>2a</b>–<b>g</b>, bis(1,2,3-triazolyl-coumarin)benzenes <b>2h</b>–<b>i</b> and coumarin-1,2,3-triazolyl-benzazole hybrids <b>4a</b>–<b>b</b>. The newly synthesised hybrid molecules were investigated for in vitro antitumour activity against five human cancer cell lines, colon carcinoma HCT116, breast carcinoma MCF-7, lung carcinoma H 460, human T-lymphocyte cells CEM, cervix carcinoma cells HeLa, as well as human dermal microvascular endothelial cells (HMEC-1). Most of these compounds showed moderate to pronounced cytotoxic activity, especially towards MCF-7 cell lines with IC<sub>50</sub> = 0.3–32 μM. In addition, compounds <b>2a</b>–<b>i</b> and <b>4a</b>–<b>b</b> were studied by UV-Vis absorption and fluorescence spectroscopy and their basic photophysical parameters were determined.https://www.mdpi.com/1420-3049/27/3/637coumarin1,2,3-triazolebenzazoleorganic synthesiscytostatic evaluationfluorescence |
| spellingShingle | Kristina Pršir Ema Horak Marijeta Kralj Lidija Uzelac Sandra Liekens Ivana Murković Steinberg Svjetlana Krištafor Design, Synthesis, Spectroscopic Characterisation and In Vitro Cytostatic Evaluation of Novel Bis(coumarin-1,2,3-triazolyl)benzenes and Hybrid Coumarin-1,2,3-triazolyl-aryl Derivatives Molecules coumarin 1,2,3-triazole benzazole organic synthesis cytostatic evaluation fluorescence |
| title | Design, Synthesis, Spectroscopic Characterisation and In Vitro Cytostatic Evaluation of Novel Bis(coumarin-1,2,3-triazolyl)benzenes and Hybrid Coumarin-1,2,3-triazolyl-aryl Derivatives |
| title_full | Design, Synthesis, Spectroscopic Characterisation and In Vitro Cytostatic Evaluation of Novel Bis(coumarin-1,2,3-triazolyl)benzenes and Hybrid Coumarin-1,2,3-triazolyl-aryl Derivatives |
| title_fullStr | Design, Synthesis, Spectroscopic Characterisation and In Vitro Cytostatic Evaluation of Novel Bis(coumarin-1,2,3-triazolyl)benzenes and Hybrid Coumarin-1,2,3-triazolyl-aryl Derivatives |
| title_full_unstemmed | Design, Synthesis, Spectroscopic Characterisation and In Vitro Cytostatic Evaluation of Novel Bis(coumarin-1,2,3-triazolyl)benzenes and Hybrid Coumarin-1,2,3-triazolyl-aryl Derivatives |
| title_short | Design, Synthesis, Spectroscopic Characterisation and In Vitro Cytostatic Evaluation of Novel Bis(coumarin-1,2,3-triazolyl)benzenes and Hybrid Coumarin-1,2,3-triazolyl-aryl Derivatives |
| title_sort | design synthesis spectroscopic characterisation and in vitro cytostatic evaluation of novel bis coumarin 1 2 3 triazolyl benzenes and hybrid coumarin 1 2 3 triazolyl aryl derivatives |
| topic | coumarin 1,2,3-triazole benzazole organic synthesis cytostatic evaluation fluorescence |
| url | https://www.mdpi.com/1420-3049/27/3/637 |
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