Synthesis and biological evaluation of 4-(1<i>H</i>-1,2,4-triazol-1-yl)benzoic acid hybrids as anticancer agents

Abuelizz, Hatem A.; Awad, Hanem M.; Marzouk, Mohamed; Nasr, Fahd A.; Alqahtani, Ali S.; Bakheit, Ahmed H.; Naglah, Ahmed M.; Al‐Salahi, Rashad

doi:10.1039/c9ra03151k

Cited by 18 publications

(11 citation statements)

References 27 publications

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“…Throughout our research, we have noticed that the 1,2,4-triazole or 1,2,3-triazole derivatives showed antioxidant properties [28][29][30][31][32][33][34][35] and demonstrated cytotoxic activity as well. In a previous work, the molecular hybridization technique was employed to incorporate the triazole unit with isothiocyanate and substituted benzylidene groups into a single molecule; the resulting targets have the potential to exhibit potent antiproliferative activity against HCT-116 and MCF-7 human cancer cell lines and showed very weak cytotoxicity against normal cells [35].…”

Section: Introductionmentioning

confidence: 79%

Biological Evaluation of 4-(1H-triazol-1-yl)benzoic Acid Hybrids as Antioxidant Agents: In Vitro Screening and DFT Study

et al. 2021

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Fourteen triazole benzoic acid hybrids were previously characterized. This work aimed to screen their in vitro antioxidant activity using different assays, i.e., DPPH (1,1-diphenyl-1-picrylhydrazyl), reducing the power capability, FRAP (ferric reducing antioxidants power) and ABTS (2,2′-azino-bis(3-ethylben zothiazoline-6-sulfonate) radical scavenging. The 14 compounds showed antioxidant properties in relation to standard BHA (butylated hydroxylanisole) and Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid). Higher antioxidant activity was observed by the parent (1) at a concentration of 100 µg/mL (89.95 ± 0.34 and 88.59 ± 0.13%) when tested by DPPH and ABTS methods in relation to BHA at 100 µg/mL (95.02 ± 0.74 and 96.18 ± 0.33%). The parent (2) demonstrated remarkable scavenging activity when tested by ABTS (62.00 ± 0.24%), however, 3 was less active (29.98 ± 0.13%). Compounds 5, 6, 9, and 11 exhibited good scavenging activity compared to 1. DFT studies were performed using the B3LYP/6-311++g (2d,2p) level of theory to evaluate different antioxidant descriptors for the targets. Three antioxidant mechanisms, i.e., hydrogen atom transfer (HAT), sequential electron transfer proton transfer (SETPT) and sequential proton loss electron transfer (SPLET) were suggested to describe the antioxidant properties of 1–14. Out of the 14 triazole benzoic acid hybrids, 5, 9, 6, and 11 showed some good theoretical results, which were in agreement with some experimental outcomes. Based on the computed (PA and ETE) and (BDE and IP) values in (SPLET) and (HAT and SETPT) mechanisms, respectively, compound 9 emerged has having good antioxidant activity.

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Section: Introductionmentioning

confidence: 79%

Biological Evaluation of 4-(1H-triazol-1-yl)benzoic Acid Hybrids as Antioxidant Agents: In Vitro Screening and DFT Study

et al. 2021

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“…Among the synthesized 4-(1 H -1,2,4-triazol-1-yl)benzoic acid hybrids 146 – 148 ( Fig. 33 ), compounds 148b (IC 50 : 15.6 μM) and 148c (IC 50 : 23.9 μM) displayed potent activity against MCF-7 and HCT-116 cancer cell lines, respectively when compared with doxorubicin (IC 50 : 19.7 and 22.6 μM, respectively) [ 134 ]. A mechanistic study illustrated that compounds 146b and 148b induced apoptosis in MCF-7 cells.…”

Section: Biological Activities Of 124-triazole Derivativesmentioning

confidence: 99%

An insight on medicinal attributes of 1,2,4-triazoles

Aggarwal

Sumran²

2020

European Journal of Medicinal Chemistry

214

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The present review aims to summarize the pharmacological profile of 1,2,4-triazole, one of the emerging privileged scaffold, as antifungal, antibacterial, anticancer, anticonvulsant, antituberculosis, antiviral, antiparasitic, analgesic and anti-inflammatory agents, etc. along with structure-activity relationship. The comprehensive compilation of work carried out in the last decade on 1,2,4-triazole nucleus will provide inevitable scope for researchers for the advancement of novel potential drug candidates having better efficacy and selectivity.

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“…The findings revealed apoptotic profile of melanoma cells after treatment with 1,2,4-triazole compounds for the first time. Apoptosis of some other cancers such as prostate, colon, breast and lung were induced by different 1,2,4-triazole derivative compounds [30][31][32]. 1,5-disubstituted 1,2,4-triazole compounds were shown to induce apoptosis and cell cycle arrest at the G 2 /M phase in cervix (HeLa) and leukemia (Jurkat) cancer cells [33].…”

Section: Int J Biol Chem (Online)mentioning

confidence: 99%

Cytotoxic effect of a 3-(4-chlorophenyl)-5-(4-methoxybenzyl)-4H-1,2,4-triazole derivative compound in human melanoma cells

Demir

Çolak

Uzuner

et al. 2021

IJBCh

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Melanoma represents the most forceful derm cancer with a high rate of mortality. Although chemotherapy has been commonly used in the treatment of melanoma, drug resistance and side effects of conventional chemotheurapeutics negatively affect the continuity and success the treatment. 1,2,4 triazole derivatives are popular compounds of recent years with anti-microbial, anti-inflammatory, analgesic, antiviral, anti-proliferative and COVID-19 associated anti-fungal activities. However, studies that revealed the effects of 1,2,4 triazole compounds on melanoma cells are limited. The aim of this study was to investigate the effects of a 3-(4-chlorophenyl)-5-(4-methoxybenzyl)-4H-1,2,4-triazole derivative (B9) compound on cytotoxicity and cell cycle using MTT and flow cytometry, respectively and the inhibitory effect on tyrosinase in human melanoma (VMM917) cells using colorimetric assay for melanin content. The compound B9 exhibited a selective cytotoxic effect (4.9-fold) on VMM917 cells compared to normal cells. B9 induced cell cycle arrest at the S phase and also decreased the amount of melanin in the cells. The results suggest a novel candidate drug in melanoma therapy. The detailed investigation of the molecular mechanism of this selective cytotoxic effect will provide understanding on the usability of B9 as an alternative chemotherapeutic agent in melanoma.

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Synthesis and biological evaluation of 4-(1H-1,2,4-triazol-1-yl)benzoic acid hybrids as anticancer agents

Abstract: A series of 4-(1H-1,2,4-triazol-1-yl)benzoic acid hybrids (1–17) was successfully synthesized and their structures were established by NMR and MS analysis. Their anticancer activity against HCT-116, MCF-7 and normal human RPE-1 cells were examined.

Cited by 18 publications

References 27 publications

Biological Evaluation of 4-(1H-triazol-1-yl)benzoic Acid Hybrids as Antioxidant Agents: In Vitro Screening and DFT Study

Biological Evaluation of 4-(1H-triazol-1-yl)benzoic Acid Hybrids as Antioxidant Agents: In Vitro Screening and DFT Study

An insight on medicinal attributes of 1,2,4-triazoles

Cytotoxic effect of a 3-(4-chlorophenyl)-5-(4-methoxybenzyl)-4H-1,2,4-triazole derivative compound in human melanoma cells

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