1,2,4-Triazole-3-Thiones: Greener, One-Pot, Ionic Liquid Mediated Synthesis and Antifungal Activity

Hassan, Mohd. Zaheen; Alsayari, Abdulrhman; Asiri, Yahya I.; Muhsinah, Abdullatif Bin

doi:10.1080/10406638.2021.2009887

Cited by 7 publications

(4 citation statements)

References 18 publications

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Section: Molecular Docking Simulationsmentioning

confidence: 99%

“…Initially, the docking protocol was validated by redocking the co-crystal ligand, acarbose, within the active site, with a cutoff of root mean square positional deviation (RMSD) < 2 Å (Figure 10) [84]. The analysis of the results of the docking simulations clearly showed that the studied compounds fitted nicely within the active site and formed hydrogen bonds, Van der Waals, π-π stacking and alkyl and π-alkyl interactions with the active site amino acid residues (Figure 11).…”

Section: Docking Against Human Pancreatic Alpha-amylase (Hpa; Pdb Id:...mentioning

confidence: 99%

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Synthesis and Biological Evaluation of Some New 3-Aryl-2-thioxo-2,3-dihydroquinazolin-4(1H)-ones and 3-Aryl-2-(benzylthio)quinazolin-4(3H)-ones as Antioxidants; COX-2, LDHA, α-Glucosidase and α-Amylase Inhibitors; and Anti-Colon Carcinoma and Apoptosis-Inducing Agents

El-Sayed,

Al-Otaibi,

Barakat

et al. 2023

Pharmaceuticals

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Oxidative stress, COX-2, LDHA and hyperglycemia are interlinked contributing pathways in the etiology, progression and metastasis of colon cancer. Additionally, dysregulated apoptosis in cells with genetic alternations leads to their progression in malignant transformation. Therefore, quinazolinones 3a–3h and 5a–5h were synthesized and evaluated as antioxidants, enzymes inhibitors and cytotoxic agents against LoVo and HCT-116 cells. Moreover, the most active cytotoxic derivatives were evaluated as apoptosis inducers. The results indicated that 3a, 3g and 5a were efficiently scavenged DPPH radicals with lowered IC50 values (mM) ranging from 0.165 ± 0.0057 to 0.191 ± 0.0099, as compared to 0.245 ± 0.0257 by BHT. Derivatives 3h, 5a and 5h were recognized as more potent dual inhibitors than quercetin against α-amylase and α-glucosidase, in addition to 3a, 3c, 3f and 5b–5f against α-amylase. Although none of the compounds demonstrated a higher efficiency than the reference inhibitors against COX-2 and LDHA, 3a and 3g were identified as the most active derivatives. Molecular docking studies were used to elucidate the binding affinities and binding interactions between the inhibitors and their target proteins. Compounds 3a and 3f showed cytotoxic activities, with IC50 values (µM) of 294.32 ± 8.41 and 383.5 ± 8.99 (LoVo), as well as 298.05 ± 13.26 and 323.59 ± 3.00 (HCT-116). The cytotoxicity mechanism of 3a and 3f could be attributed to the modulation of apoptosis regulators (Bax and Bcl-2), the activation of intrinsic and extrinsic apoptosis pathways via the upregulation of initiator caspases-8 and -9 as well as executioner caspase-3, and the arrest of LoVo and HCT-116 cell cycles in the G2/M and G1 phases, respectively. Lastly, the physicochemical, medicinal chemistry and ADMET properties of all compounds were predicted.

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Section: Molecular Docking Simulationsmentioning

confidence: 99%

Section: Docking Against Human Pancreatic Alpha-amylase (Hpa; Pdb Id:...mentioning

confidence: 99%

Synthesis and Biological Evaluation of Some New 3-Aryl-2-thioxo-2,3-dihydroquinazolin-4(1H)-ones and 3-Aryl-2-(benzylthio)quinazolin-4(3H)-ones as Antioxidants; COX-2, LDHA, α-Glucosidase and α-Amylase Inhibitors; and Anti-Colon Carcinoma and Apoptosis-Inducing Agents

El-Sayed,

Al-Otaibi,

Barakat

et al. 2023

Pharmaceuticals

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“…It contributes to the activity by the bonds it forms with the HEM in the active site of the 14-α-demethylases enzyme. When the literature is examined, it has been proven by many studies that this ring has antifungal activity. − There are literature studies showing the antifungal activities of not only 1,3,4-triazoles but also 1,2,4-triazoles and 1,2,3 triazoles. − …”

Section: Introductionmentioning

confidence: 99%

“… 11 − 19 There are literature studies showing the antifungal activities of not only 1,3,4-triazoles but also 1,2,4-triazoles and 1,2,3 triazoles. 20 − 24 …”

Section: Introductionmentioning

confidence: 99%

Synthesis, Antifungal Activities, Molecular Docking and Molecular Dynamic Studies of Novel Quinoxaline-Triazole Compounds

Osmaniye,

Baltacı Bozkurt,

Levent

et al. 2023

ACS Omega

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Uncontrolled use of antifungal drugs affects the development of resistance to existing drugs. Azole antifungals constitute a large part of antifungal therapy. Therefore, there is a need for new azole antifungals. Within the scope of this study, 17 new triazole derivative compounds were synthesized. Structure determinations were clarified by spectroscopic analysis methods ( 1 H-NMR, 13 C-NMR, HRMS). In addition, structure matching was completed using two-dimensional NMR techniques, HSQC, HMBC and NOESY. The antifungal effects of the compounds were evaluated on Candida strains by means of in vitro method. Compound 5d showed activity against Candida glabrata with a MIC 90 = 2 μg/mL. Compound 5d showed activity against Candida krusei with a MIC 90 = 2 μg/mL. This activity value, which is higher than fluconazole, is promising. In addition, the biofilm inhibition percentages of the compounds were calculated. Molecular docking and molecular dynamics simulations performed with compound 5d are in harmony with activity studies.

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New Benzylidene‐Triazole Tethered Coumarin Molecular Hybrids: Synthesis, SAR, Molecular Modelling Simulations Targeting Tubulin α/β Dimer and its Antimicrobial Evaluation

Manda,

Nadh,

Angajala

et al. 2024

ChemistrySelect

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A series of new 7‐{3‐[3‐(Benzylidene‐amino)‐[1,2,4]triazole‐1‐yl]‐propoxy}‐4‐methyl‐chromen‐2‐one molecular hybrids 7(a–k) were synthesized using molecular hybridization approach. The synthesized new benzylidene‐triazole tethered coumarin molecular hybrids were characterized by spectroscopic studies and elemental analysis. The coumarin molecular hybrids have been explored for their antifungal efficacy in terms of tubulin inhibitors using molecular modelling studies against tubulin alphabeta hetero dimer protein. The results clearly demonstrated strong binding affinity of coumarin molecular hybrids with indole substituted and 2,4‐dihydroxy substituted as antagonists with respective binding scores of −10.5 and −10.7 kcal/mol towards tubulin alphabeta hetero dimer protein which was higher in comparison to standards griseofulvin (−8.2 kcal/mol) and fluconazole (−8.1 kcal/mol). In addition, broth dilution method was used to conduct in‐vitro antifungal studies against three fungal strains namely Candida albicans, Aspergillus niger and Aspergillus fumigatus. The results obtained clearly illustrate the antifungal activity of indole and 2,4‐dihydroxy substituted compounds which are consistent with docking simulations. Out of all the synthesized molecular hybrids, indole and 2,4‐dihydroxy substituted compounds depict outstanding antifungal activity with Minimum Inhibitory Concentration (MIC) value of 31.25 μg/ml and 62.5 μg/ml towards C.albicans and with MIC value of 31.25 for both these molecules towards A.niger in each case which is quite higher than griseofulvin and fluconazole respectively. Present work clearly demonstrates the potential efficacy of synthesized indole and 2,4‐dihydroxy substituted coumarin molecular hybrids to be considered as lead compounds for the development of new agents against resistant strains for the treatment of fungal infection.

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1,2,4-Triazole-3-Thiones: Greener, One-Pot, Ionic Liquid Mediated Synthesis and Antifungal Activity

Cited by 7 publications

References 18 publications

Synthesis and Biological Evaluation of Some New 3-Aryl-2-thioxo-2,3-dihydroquinazolin-4(1H)-ones and 3-Aryl-2-(benzylthio)quinazolin-4(3H)-ones as Antioxidants; COX-2, LDHA, α-Glucosidase and α-Amylase Inhibitors; and Anti-Colon Carcinoma and Apoptosis-Inducing Agents

Synthesis and Biological Evaluation of Some New 3-Aryl-2-thioxo-2,3-dihydroquinazolin-4(1H)-ones and 3-Aryl-2-(benzylthio)quinazolin-4(3H)-ones as Antioxidants; COX-2, LDHA, α-Glucosidase and α-Amylase Inhibitors; and Anti-Colon Carcinoma and Apoptosis-Inducing Agents

Synthesis, Antifungal Activities, Molecular Docking and Molecular Dynamic Studies of Novel Quinoxaline-Triazole Compounds

New Benzylidene‐Triazole Tethered Coumarin Molecular Hybrids: Synthesis, SAR, Molecular Modelling Simulations Targeting Tubulin α/β Dimer and its Antimicrobial Evaluation

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