A One-Pot Six-Component Reaction for the Synthesis of 1,5-Disubstituted Tetrazol-1,2,3-Triazole Hybrids and Their Cytotoxic Activity against the MCF-7 Cell Line (original) (raw)
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In an effort to improve and achieve biologically active anticancer agents, a novel series of 1,2,3-triazole-containing hybrids were designed and efficiently synthesized via the Cu-catalyzed azide-alkyne cycloaddition (CuAAC) reaction of substituted-arylazides with alkyne-functionalized pyrazole-[1,2,4]-triazole hybrids. The structure geometry of these new clicked 1,2,3-triazoles was explored by density functional theory (DFT) using the B3LYP/6-311++G(d,p) level; also, the potential activity of the compounds for light absorption was simulated by time-dependent DFT calculations (TD-DFT). The antitumor impacts of the newly synthesized compounds were in vitro estimated to be towards the human liver cancer cell line (HepG-2), the human colon cancer cell line (HCT-116), and human breast adenocarcinoma (MCF-7). Among the tested compounds, conjugate 7 was the most potent cytotoxic candidate towards HepG-2, HCT-116, and MCF-7, with IC50 = 12.22, 14.16, and 14.64 µM, respectively, in comparis...
Mediterranean Journal of Chemistry, 2019
The present study established the efficient separate synthesis of four unique 1, 2, 3-triazole derivatives (M1, M2, M3, M4) via conducting 1,3-dipolar cycloaddition of N-((4-azidophenyl) sulfonyl) acetamide, with substituted N-phenylmaleimide. FTIR, 1H NMR, 13C NMR, and mass spectra were utilized for the characterization of the triazoles. The cytotoxic activities of these compounds, with regards to breast cancer cell lines (MDA-MB-231), were then evaluated. The cytotoxicity pre-screening outcomes for 100 µM portrayed a variety of actions, while the IC50 values with concentrations of 0-500 µM for 48 hours, the results are 2.542, 2.929, 2.429, and 2.864 µM for the compounds M1, M2, M3, and M4 respectively. Remarkably, the M2 and M4 para -substituted compounds exhibited superior IC50 values, in comparison to the M1 and M3 ortho -substituted compounds. This suggests that the M1 and M3 compounds have the potential to perform as against breast cancer.
Design, synthesis and evaluation of novel 1,2,4-triazole derivatives as promising anticancer agents
BMC Chemistry
Herein, we reported the synthesis of nineteen novel 1,2,4-triazole derivatives including 1,3-diphenyl-2-(1H-1,2,4-triazol-1-yl) propan-1-ones (7a-e), 1-(1,3-diphenylpropan-2-yl)-1H-1,2,4-triazole (8a-c) and 1,4-diphenyl-2-(1H-1,2,4-triazol-1-yl) butane-1,4-diones (10a-k). The structures of these derivatives were confirmed by spectroscopic techniques like IR, 1H-NMR, Mass spectroscopy and Elemental analysis. The cytotoxic activities of the synthesized compounds were evaluated against three human cancer cell lines including MCF-7, Hela and A549 using MTT assay. Compounds 7d, 7e, 10a and 10d showed a promising cytotoxic activity lower than 12 μM against Hela cell line. The safety of these compounds was also, evaluated on MRC-5 as a normal cell line and relieved that most of the synthesized compounds have proper selectivity against normal and cytotoxic cancerous cell lines. Finally, molecular docking studies were also, done to understand the mechanism and binding modes of these derivati...
Synthesis of novel 1,2,3-triazole-based hybrids via click reactions
Arkivoc, 2021
1,2,3-Triazoles have attracted the interest of researchers due to their wide range of biological activities which include antitumor, anti-leishmanial, bioluminescent and fungicidal activities This paper describes the synthesis of novel triazole hybrids containing biologically active fragments through cycloaddition (click) reactions, with the aim of increasing the diversity of known and active 1,2,3-triazole derivatives. All new compounds have been characterized by physicochemical methods.
Synthesis, Cytotoxic Activity Study of 1,2,3-Triazole Derivatives Based on Metronidazole
Cognizance Journal of Multidisciplinary Studies (CJMS), 2024
This study focuses on the synthesis and cytotoxic evaluation of 1,2,3-triazole derivatives based on metronidazole, a widely used antiparasitic and antibacterial drug. Employing click chemistry, novel derivatives were synthesized by reacting propargylic ether derivatives of metronidazole with various aryl azide compounds. The structures of the synthesized compounds were confirmed through FTIR and 1H-NMR spectroscopy. Their cytotoxic potential was assessed using the MTT assay against the A549 human cancer cell line. The results demonstrated moderate inhibitory activity, with IC50 values ranging from 9.06 µM to 12.67 µM. These findings highlight the potential of these derivatives as effective tumor cell inhibitors, suggesting further exploration for anticancer therapeutic development.
2,3-Triazoles: A Review on Current Trends in Synthetic and Biological Applications
The chemistry of 1,2,3-triazoles gained much attention since the discovery by Pechmann, since then several protocols have been developed for the synthesis of 1,2,3-triazoles, but after the copper catalyzed alkyne-azide cycloaddition (CuAAC) reaction, the mainly because of Huisgen's 1,3-dipolar cycloaddition reactions, it has evolved to become one of the most successful connective linkers and functional heterocyclic cores in modern organic chemistry. This review summarizes the up-to date developments in the synthetic methodologies and their biological applications, in particular of antimicrobial, anticancer, anti-inflammatory, anti-proliferative, antidiabetic properties of 1,2,3-triazoles. Also, the progress in the molecular hybridization; and physic-chemical properties have been highlighted.
Synlett, 2020
In this work, 21 novel (1,4-disubstituted 1,2,3-triazole)-dihydropyrimidinone (1,2,3-trzl-DHPM) type hybrids were synthesized and characterized. These were divided into two types: hybrids A (5 in total) containing the dihydropyrimidinone heterocyclic ring decorated with a 1,4-disubstituted 1,2,3-triazole in the C-5 position [these compounds were accessed by a multicomponent copper(I)-catalyzed azide alkyne cycloaddition (CuAAC) (or click)–Biginelli reactions with satisfactory yields (39–57%)] and hybrids B (16 in total) containing two 1,2,3-triazole units in the C-5 and C-6 methyl position of the DHPM. Hybrids B were synthesized via functionalization of the C-6 methyl group of hybrids A, a multistep sequence of reactions was used that included bromination, azidation, and a CuAAC. Hybrids B were obtained in very good to excellent yields (up to 99%). Some hybrids A and B were evaluated for their antiproliferative activity against different cancer cell lines that included A549 and SW15...
IJC-B Vol.60B(03) [March 2021], 2021
Over the past decade, a variety of benzothiazole derivatives have been reported with promising anticancer activity. Benzothiazole and its analogues are capable of acting on a number of molecular targets and thus exerting their anticancer activity. To further develop benzothiazole derivatives as anticancer agents, we attempted to design and synthesize a library of benzothiazole-triazole derivatives. The synthesized hybrid compounds have been selected by National Cancer Institute, USA for the in vitro activity evaluation against 60 human cancer cell lines in a one dose screening panel. Most of the synthesized compounds showed 60-80% growth rate against renal cancer cell line UO-31.
Synthesis and anticancer activity evaluation of new 1,2,3-triazole-4-carboxamide derivatives
Medicinal Chemistry Research, 2013
ABSTRACT Anticancer screening of several novel 1,2,3-triazoles has been performed. The 1,2,3-triazole derivatives were synthesized from available starting materials according to the convenient synthetic procedures using a multicomponent reaction which gave a wide access to triazole derivatives production. The synthesized compounds were tested for their anticancer activity in NCI60 cell lines. It was observed that some compounds showed remarkable anticancer activity. Two of them possessed a significant activity on leukemia, melanoma, non-small cell lung, CNS, ovarian, renal, and breast cancer. 5-Amino-1-p-tolyl-1H-[1,2,3]triazole-4-carboxylic acid (2,5-dichloro-phenyl)-amide showed a significant correlation in COMPARE analysis. Graphical Abstract 1,2,3-triazole-4-carboxamide derivatives were synthesized in a simple and convenient synthetic path, their in vitro anticancer activity was examined after the performance of molecular docking.
New series of benzothiazole-1,2,3-triazoles; appended with benzothiazole, isatin and/or benzimidazole moiety; were designed and synthesized through the click chemistry approach. The syntheses proceeded [Cu(I) catalyzed] 1,3-dipolar cycloaddition between the appropriate alkyne based benzothiazole, isatin and/or benzimidazole with un/substituted benzothiazole azide. The synthesized compounds were characterized by FT-IR, Mass and NMR methods. The DNA binding constants (Kb) were in the range of 1.732 Â 10 5 to 3.191 Â 10 5 M À1 ; indicating good binding tendency of the compounds with DNA. Nearly all the compounds intercalated with DNA through the minor grooves via covalent, intercalative and electrostatic bondings. Total nine compounds indicated more than 50% anticancer activities with colorectal (SW182) and lung (H199) cancer cell lines. The docking studies indicated quite good binding affinities (À3.7 to À5.4 kcal/mol) of the reported compounds with DNA. The experimental results of DNA bindings were in good agreement with those of docking studies. The reported compounds may be potential future candidates for anticancer treatment.