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

• Published in: Molecules (Basel, Switzerland) Vol. 27; no. 3; p. 637
• Main Authors: Pršir, Kristina, Horak, Ema, Kralj, Marijeta, Uzelac, Lidija, Liekens, Sandra, Steinberg, Ivana Murković, Krištafor, Svjetlana
• Format: Journal Article
• Language: English
• Published: Switzerland MDPI AG 19.01.2022; MDPI
• Subjects: 1,2,3-triazole; Alkynes; benzazole; Breast cancer; Breast carcinoma; Cancer; Cervical carcinoma; Cervix; Colon; Colon cancer; Coumarin; Cycloaddition; cytostatic evaluation; Cytotoxicity; Endothelial cells; Fluorescence; Fluorescence spectroscopy; Hybrids; Lung carcinoma; Lymphocytes; Lymphocytes T; Microvasculature; organic synthesis; Tumor cell lines; cytostatic evaluation; benzazole; fluorescence; organic synthesis; 1,2,3-triazole; coumarin
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules27030637

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 - , bis(1,2,3-triazolyl-coumarin)benzenes - and coumarin-1,2,3-triazolyl-benzazole hybrids - . 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 = 0.3-32 μM. In addition, compounds - and - were studied by UV-Vis absorption and fluorescence spectroscopy and their basic photophysical parameters were determined.