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

Pršir, Kristina; Horak, Ema; Kralj, Marijeta; Uzelac, Lidija; Liekens, Sandra; Murković Steinberg, Ivana; Krištafor, Svjetlana (2022) 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, 27 (3). ISSN 1420-3049

Preview

PDF - Published Version - article
Available under License Creative Commons Attribution.
Download (2MB) | Preview

Official URL: https://www.mdpi.com/1420-3049/27/3/637

Abstract

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 2a–g, bis(1, 2, 3-triazolyl-coumarin)benzenes 2h–i and coumarin-1, 2, 3-triazolyl-benzazole hybrids 4a–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 IC50 = 0.3–32 μM. In addition, compounds 2a–i and 4a–b were studied by UV-Vis absorption and fluorescence spectroscopy and their basic photophysical parameters were determined.

Item Type:

Article

Uncontrolled Keywords:

coumarin ; 1, 2, 3-triazole ; benzazole ; organic synthesis ; cytostatic evaluation ; fluorescence

Subjects:

NATURAL SCIENCES > Chemistry

Divisions:

Division of Molecular Medicine

Projects:

Project title	Project leader	Project code	Project type
Dizajn i sinteza novih dušikovih heterocikličkih fluorofora i fluorescentnih nanomaterijala kao kemijskih senzora za pH i metalne ione	Vianello, Robert	IP-2014-09-3386	HRZZ

Depositing User:

Lidija Uzelac

Date Deposited:

11 Mar 2022 10:29

URI:

http://fulir.irb.hr/id/eprint/7067

DOI:

10.3390/molecules27030637