Anticancer properties of newly synthesized Triazoles (14a) against cervical and breast cancer cell lines (original) (raw)
Related papers
Triazole: A Potential Anticancer Agent
Despite a significant work on 1, 2, 4-triazoles, continuous efforts are still being made to identify novel heterocyclic compounds with potent biological activities. Scientists develop a lot of new compounds having 1, 2, 4-triazole nucleus and screened them for their different biological activities such as antimicrobial, anticonvulsant, analgesic, anti-inflammatory, antimalarial, antiulcer, antihistaminic, antiprotozoal, antitubercular, antiviral and anticancer. This review focuses on the various synthetic approaches of triazole derivatives and their anticancer activity.
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.
In Vitro Anticancer Properties of Novel Bis-Triazoles
Current Issues in Molecular Biology
Here, we describe the anticancer activity of our novel bis-triazoles MS47 and MS49, developed previously as G-quadruplex stabilizers, focusing specifically upon the human melanoma MDA-MB-435 cell line. At the National Cancer Institute (NCI), USA, bis-triazole MS47 (NCS 778438) was evaluated against a panel of sixty human cancer cell lines, and showed selective, distinct multi-log differential patterns of activity, with GI50 and LC50 values in the sub-micromolar range against human cancer cells. MS47 showed highly selective cytotoxicity towards human melanoma, ovarian, CNS and colon cancer cell lines; in contrast, the leukemia cell lines interestingly showed resistance to MS47 cytotoxic activity. Further studies revealed the potent cell growth inhibiting properties of MS47 and MS49 against the human melanoma MDA-MB-435 cell line, as verified by MTT assays; both ligands were more potent against cancer cells than MRC-5 fetal lung fibroblasts (SI > 9). Melanoma colony formation was s...
DESIGN, SYNTHESIS AND IN VITRO ANTI-CANCER ACTIVITY OF NOVEL 1,2,4-TRIAZOLE DERIVATIVES
International journal of Pharmacy and Pharmaceutical Sciences, 2014
Objective: DNA topoisomerase is one of the important targets for anticancer agents. Many triazole derivatives have been shown to possess cytotoxic activity. In this paper, we present the design and in silico docking of a virtual library of molecules with DNA topoisomerase II along with their synthesis and In vitro cytotoxicity profile. Methods: Sybyl X 2.1 programmesss were used to perform the docking experiments on DNA topoisomerase II using etoposide as ligand. In vitro anticancer activity was carried out by trypan blue exclusion assay against EAC cells. DNA fragmentation studies were performed by Gel electrophoresis to identify the cause of cell death induced by these compounds. Results: Among the compounds studied for docking, 12c generated the highest docking score (13.66) and showed hydrogen bonding interactions with glycine 778 at a distance of 1.879 A˚. the compounds 12c & 12g showed the highest level of cytotoxicity with IC50 value of 0.55 μM and 0.62 μM respectively. Compounds 12c and12g were subjected to DNA fragmentation studies to identify the cause of cell death induced by these compounds. Gel electrophoresis of these compounds showed a typical feature of apoptosis ladders in agarose gel. Compound 12c was able to induce apoptosis at a concentration of about 3 μM. Conclusion: A series of bis-triazoles were synthesized targeted to DNA topoisomerase II and evaluated their In vitro cytotoxicity. The compound 12c was found to be most active and also exhibited apoptosis inducing potential.
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...
In the present study, two important starting materials and 18 new 1,2,4-triazole compounds with mono ring system have been synthesized and characterized. The mono system showed 16 compounds of a Schiff base moiety attached to the triazole ring which was prepared from the corresponding starting material 5(AeB) or piperidinium salt system 6(AeB). All these compounds were characterized using Fourier Transform Infrared (FT-IR) and Nuclear Magnetic Resonance (NMR) spectroscopy and carbon hydrogen nitrogen (CHN) elemental analysis. The compounds were selected for in vitro anticancer study to test the therapeutic cytotoxic potential against cancer cells. The MTT test was conducted against human breast (MCF-7) and colorectal (HCT-116) cancer cells. Among all the compounds tested, 7A-i demonstrated more pronounced in vitro anticancer effect against MCF-7 and HCT-116 cells with IC 50 of 38 and 19.2 mM, respectively, comparable to that of the standard reference drugs, tamoxifen and 5fluorouracil, respectively. Compound 7A-vi showed a considerable cytotoxic effect with IC 50 53 and 41.2 mM against MCF-7 and HCT-116 cells, respectively. Compounds 7A-ii, 7A-iii and 7A-v exhibited moderate cytotoxicity with IC 50 68, 91 and 85 mM, respectively against MCF-7 cells and also 59.3, 81.7 and 137.1 mM against HCT-116 cells, respectively. However, all other compounds tested in this study showed poor cytotoxicity against both the cell lines. Cellular morphological analysis revealed that the cytotoxicity induced by the compounds could probably due to autophagy. It can be concluded that 1,2,4-triazole derivatives can be promising therapeutic agents. Further studies will be done to investigate the antitumor efficacy of the 1,2,4-triazole derivatives using suitable preclinical models.
Medicinal attributes of 1,2,3-triazoles: Current developments
Bioorganic Chemistry, 2017
1,2,3-Triazoles are important five-membered heterocyclic scaffold due to their extensive biological activities. This framework can be readily obtained in good to excellent yields on the multigram scale through click chemistry via reaction of aryl/alkyl halides, alkynes and NaN 3 under ambient conditions. It has been an emerging area of interest for many researchers throughout the globe owing to its immense pharmacological scope. The present work aims to summarize the current approaches adopted for the synthesis of the 1,2,3-triazole and medicinal significance of these architectures as a lead structure for the discovery of drug molecules such as COX-1/COX-2 inhibitors (celecoxib, pyrazofurin), HIV protease inhibitors, CB1 cannabinoid receptor antagonist and much more which are in the pipeline of clinical trials. The emphasis has been given on the major advancements in the medicinal prospectus of this pharmacophore for the period during 2008-2016. 1. Introduction 2. Synthetic Strategies 2.1 Metal free synthesis of 1,2,3-Triazoles 2.2 Metal-catalyzed synthesis of 1,2,3-Triazoles 3. Biological Activity 3.1 Anti-cancer Activity 3.2 Anti-inflammatory activity 3.3 Antitubercular activity 3.4 Antileishmanial and antitrypanosomal activity 3.5 Antimicrobial activity 3.6 Antiviral activity 3.7 Antibacterial activity 3.8 Miscellaneous 4. Conclusion
Acta Chimica Slovenica, 2016
This article demonstrates the synthesis of 1,2,4-triazole derivatives and their applications in medicine particularly as anti-breast cancer agents which is a major issue of the present. The synthesized compounds were characterized by elemental analysis, FT-IR and NMR. DFT was used to study the quantum chemical calculations of geometries and vibrational wave numbers of 3-hydroxynaphthyl and p-tolyl substituted 1,2,4-triazoles in the ground state. The scaled harmonic vibrational frequencies obtained from the DFT method were compared with those of the FT-IR spectra and found good agreement. The synthesized 1,2,4-triazole-naphthyl hybrids were screened for the anticancer activity against MCF-7 breast cancer lines. Among them compounds 3 and 7 showed broad spectrum anticancer activity with IC 50 values 9.7 μM and 7.10 μM, respectively and their activity is comparable to that of the standard drugs. The molecular model for binding between the compounds (1-8) and the active site of BRCA2 was obtained on the basis of the computational docking results and the structure-activity relationship.