Synthesis, biological evaluation and computational studies of fused acridine containing 1,2,4-triazole derivatives as anticancer agents

Mahanti, Srinivas; Sunkara, Satyaveni; Bhavani, Ram

doi:10.1080/00397911.2019.1608450

Cited by 22 publications

(9 citation statements)

References 18 publications

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“… 16 − 18 It is important to note that 1,2,4-triazole-containing anti-cancer drugs such as letrazole and anastrozole ( Figure 1 ) are already in use for the treatment of breast cancer. 19 …”

Section: Introductionmentioning

confidence: 99%

“…In this regard, 1,2,4-triazole-derived heterocycles have gained significant attention in the last few years owing to their chemotherapeutic values. , The literature reveals that 1,2,4-triazole derivatives hold numerous therapeutic features such as analgesic, anti-microbial, , local anesthetic, anti-inflammatory, anti-malarial, anti-convulsant, anti-viral, anti-neoplastic, and anti-cancer activities. − It is important to note that 1,2,4-triazole-containing anti-cancer drugs such as letrazole and anastrozole (Figure ) are already in use for the treatment of breast cancer …”

Section: Introductionmentioning

confidence: 99%

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Synthesis, Hemolytic Studies, and In Silico Modeling of Novel Acefylline–1,2,4-Triazole Hybrids as Potential Anti-cancer Agents against MCF-7 and A549

et al. 2021

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A series of novel theophylline-7-acetic acid (acefylline)-derived 1,2,4-triazole hybrids with N -phenyl acetamide moieties ( 11a – j ) have been synthesized and tested for their inhibitory ( in vitro ) potential against two cancer cell lines, A549 (lung) and MCF-7 (breast), using MTT assay. Among these derivatives, 11a , 11c , 11d , 11g , and 11h displayed remarkable activity against both cancer cell lines having cell viability values in the 21.74 ± 1.60–55.37 ± 4.60% range compared to acefylline (86.32 ± 1.75%) using 100 μg/μL concentration of compounds. These compounds were further screened against the A549 cancer cell line (lung) to find their half-maximal inhibitory concentration (IC 50 ) by applying various concentrations of these compounds. Compound 11g (2-(5-((1,3-dimethyl-2,6-dioxo-2,3-dihydro-1 H -purin-7(6 H )-yl)methyl)-4-phenyl-4 H -1,2,4-triazol-3-ylthio)- N - p -tolylacetamide) with the least IC 50 value (1.25 ± 1.36 μM) was discerned as a strong inhibitor of cancer cell multiplication in both cell lines (A549 and MCF-7). Their hemolytic studies revealed that all of them had very low cytotoxicity. Finally, in silico modeling was carried out to find the mode of binding of the highly active compound ( 11g ), which was according to the results of anti-cancer activity.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, Hemolytic Studies, and In Silico Modeling of Novel Acefylline–1,2,4-Triazole Hybrids as Potential Anti-cancer Agents against MCF-7 and A549

et al. 2021

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“…Triazole derivatives have attracted considerable interest in the scientific community due to their vast range of biological activities. In addition to antifungal action [ 14 , 15 , 16 , 17 , 18 , 19 ], they were shown to possess other antimicrobial effects such as antibacterial, including anti-tuberculous activity [ 20 , 21 , 22 , 23 , 24 ], antiparasitic [ 25 , 26 , 27 ] and anti-HIV effects [ 28 ] as well as anticholinesterase [ 29 ], antiangiogenic [ 30 ], anticancer [ 31 , 32 ], antidiabetic [ 33 , 34 ] and anticonvulsant activities [ 35 ].…”

Section: Introductionmentioning

confidence: 99%

Chromenol Derivatives as Novel Antifungal Agents: Synthesis, In Silico and In Vitro Evaluation

et al. 2021

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Herein we report the synthesis of some new 1H-1,2,4-triazole functionalized chromenols (3a–3n) via tandem reactions of 1-(alkyl/aryl)-2-(1H-1,2,4-triazole-1-yl) with salicylic aldehydes and the evaluation of their antifungal activity. In silico prediction of biological activity spectra with computer program PASS indicate that the compounds have a high novelty compared to the known antifungal agents. We did not find any close analog among the over 580,000 pharmaceutical agents in the Cortellis Drug Discovery Intelligence database at the similarity cutoff of 70%. The evaluation of antifungal activity in vitro revealed that the highest activity was exhibited by compound 3k, followed by 3n. Their MIC values for different fungi were 22.1–184.2 and 71.3–199.8 µM, respectively. Twelve from fourteen tested compounds were more active than the reference drugs ketoconazole and bifonazole. The most sensitive fungus appeared to be Trichoderma viride, while Aspergillus fumigatus was the most resistant one. It was found that the presence of the 2-(tert-butyl)-2H-chromen-2-ol substituent on the 4th position of the triazole ring is very beneficial for antifungal activity. Molecular docking studies on C. albicans sterol 14α-demethylase (CYP51) and DNA topoisomerase IV were used to predict the mechanism of antifungal activities. According to the docking results, the inhibition of CYP51 is a putative mechanism of antifungal activity of the novel chromenol derivatives. We also showed that most active compounds have a low cytotoxicity, which allows us to consider them promising antifungal agents for the subsequent testing activity in in vivo assays.

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“…This problem is mainly due to the increasing resistance of pathogenic microorganisms to antibiotics applied in clinical practice. Heterocyclic compounds have major role in the design and investigations of new bioactive drugs possessing heteroaromatic polycyclic molecule acridine derivatives which are well known for their DNA intercalating activities and pharmacological activity [10][11][12][13].…”

Section: Original Research Articlementioning

confidence: 99%

Synthesis, Characterisation and Antimicrobial Evaluations of Acetyloxyphenyl-1,2,3-triazole Linked Hexahydro Acridinediones

Shanmugasundaram

Sujatha²,

Aanandhi

et al. 2022

JPRI

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Synthesis, biological evaluation and computational studies of fused acridine containing 1,2,4-triazole derivatives as anticancer agents

Cited by 22 publications

References 18 publications

Synthesis, Hemolytic Studies, and In Silico Modeling of Novel Acefylline–1,2,4-Triazole Hybrids as Potential Anti-cancer Agents against MCF-7 and A549

Synthesis, Hemolytic Studies, and In Silico Modeling of Novel Acefylline–1,2,4-Triazole Hybrids as Potential Anti-cancer Agents against MCF-7 and A549

Chromenol Derivatives as Novel Antifungal Agents: Synthesis, In Silico and In Vitro Evaluation

Synthesis, Characterisation and Antimicrobial Evaluations of Acetyloxyphenyl-1,2,3-triazole Linked Hexahydro Acridinediones

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