Recent advances in the chemistry of 1,2,4-triazoles: Synthesis, reactivity and biological activities

Abdelli, Abderrahmen; Azzouni, Safa; Plais, Romain; Gaucher, Anne; Efrit, Mohamed Lotfi; Prim, Damien

doi:10.1016/j.tetlet.2021.153518

Cited by 75 publications

(36 citation statements)

References 63 publications

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“…Various synthetic approaches were developed to synthesize 1,2,4-triazole and its derivative's from common precursors like imidates, hydrazone, metal-based approach, cycloaddition reaction etc. [21][22][23][24][25][26] Basically 1,2,4triazole has two tautomeric form, 1H-1,2,4-triazole and 4H-1,2,4-triazole as shown in Figure 1, but 1H-1,2,4triazole is more stable comparatively. [27] 1,2,4-triazole has high affinity with biological receptor and it might be due to its structural rigidity and dipole properties via forming a variety of interactions like electrostatic interactions, p-p conjugation, hydrogen bonding, hydrophobicity, and van der Waals force of interaction.…”

Section: Introductionmentioning

confidence: 99%

“…1,2,4‐triazoles are derived from pyrazole via substituting carbon by nitrogen atom at position 4, it acts as isosteres of ester, amide and carboxylic acid. Various synthetic approaches were developed to synthesize 1,2,4‐triazole and its derivative's from common precursors like imidates, hydrazone, metal‐based approach, cycloaddition reaction etc [21–26] . Basically 1,2,4‐triazole has two tautomeric form, 1 H ‐1,2,4‐triazole and 4 H ‐1,2,4‐triazole as shown in Figure 1, but 1 H ‐1,2,4‐triazole is more stable comparatively [27] .…”

Section: Introductionmentioning

confidence: 99%

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Synthetic and Medicinal Perspective of 1,2,4‐Triazole as Anticancer Agents

Rathod

Kumar

2022

Chemistry & Biodiversity

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Cancer is still one of the leading causes of death worldwide. Many researchers are working to design and develop heterocyclic-based drugs with the potential to treat cancer at various stages. There is always an unmet need to discover new anticancer drugs to treat different types of cancer. Based on literature reports, it was evident that hybrid 1,2,4-triazoles exhibit a wide spectrum of biological potential (particularly potent anticancer activity), as compared to the corresponding monocyclic compounds. In this review, we summarized fused/hybrid 1,2,4-triazole and poly-functionalized 1,2,4-triazoles as anticancer agents. Triazole may be fused with other heterocyclic scaffolds like pyrimidine, pyridine, piperidine, quinoxaline, quinazoline, thiadiazine, indole, phthalazine etc. A clear explanation of the method of synthesis, structure-activity relationship, and in vitro results plus the inhibitory concentration of new molecules are focused on in this review article.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthetic and Medicinal Perspective of 1,2,4‐Triazole as Anticancer Agents

Rathod

Kumar

2022

Chemistry & Biodiversity

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“…1,2,4-triazole derivatives occupy a great place in medicinal chemistry field [11]. The triazole ring system presents a significant pharmacophore group with the ability of high receptor affinity the besides the weak cyctotoxic effect in human normal cells [12], [13]. These features mostly depend on their dipole moment, rigidity and solubility [14].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structure elucidation and cytotoxic activities of 2,5-disubstituted-1,3,4-thiadiazole and l,2,4-triazole-3-thione derivatives

KANDEMİR,

KARAKUŞ,

ÖZBAŞ

et al. 2022

jrp

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In this study, a series of 1,3,4-thiadiazole (1b-9b) and l,2,4-triazole-3-thione (1c-9c) derivatives were synthesized. The reaction proses was carried out with the cyclocondensation of suitable 1,4-disubstituted thiosemicarbazide derivatives (1a-9a). The structures of the synthesized compounds were confirmed by the data obtained from elemental analysis, HPLC, UV, IR, 1 H-NMR and MS spectra. All of the compounds were tested for their cytotoxic activities against L929 fibroblast cells by MTT method. It was determined that the tested compounds 1a-9a, 1b-9b and 1c-9c were not cytotoxic at the studied concentrations (5.0 µg/mL and 10.0 µg/mL) in L929 cell lines. Compounds 1a-c, 2a-c, 3a-c, 4a-c, 5a-c and 8a-c showed increased growth inhibition whereas compounds 6a-c, 7a-c and 9a-c showed decreased growth inhibition on L929 cell lines

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“…Chemists are interested in 1,2,4-triazole derivatives mainly because of their wide range of pharmacological activities, such as antifungal, herbicidal, antiviral and anticancer activities, as well as catalase inhibitors. Some drugs that are clinically used for the treatment of various diseases are based on them [1][2][3][4][5][6][7][8]. Commercial fungicides also contain triazoles [9].…”

Section: Introductionmentioning

confidence: 99%

3-Phenyl-4-(prop-2-en-1-yl)-5-[(prop-2-en-1-yl)sulfanyl]-4H-1,2,4-triazole

Slyvka

Goreshnik

Fedko

et al. 2022

Molbank

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1,2,4-Triazoles appear to be attractive substances due to their wide range of applications. Previously 3-phenyl-4-(prop-2-en-1-yl)-5-[(prop-2-en-1-yl)sulfanyl]-4H-1,2,4-triazole (Atr) has proven to be an effective precursor for us to prepare Cu(I)-π,σ-coordination compounds with nonlinear optical and magnetic properties. In this study, we present the structural characterization of Atr by a single-crystal X-ray diffraction method. The crystals are monoclinic, Sp.gr. P21, Z = 2, unit cell dimensions: a = 5.6967(3), b = 7.8045(3), c = 14.9327(7) Å, β = 91.113(4)°, V = 663.78(5) Å3 at 150 K. To analyze the intermolecular interactions in the crystal structure of Atr, a DFT computational study was also performed.

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Recent advances in the chemistry of 1,2,4-triazoles: Synthesis, reactivity and biological activities

Cited by 75 publications

References 63 publications

Synthetic and Medicinal Perspective of 1,2,4‐Triazole as Anticancer Agents

Synthetic and Medicinal Perspective of 1,2,4‐Triazole as Anticancer Agents

Synthesis, structure elucidation and cytotoxic activities of 2,5-disubstituted-1,3,4-thiadiazole and l,2,4-triazole-3-thione derivatives

3-Phenyl-4-(prop-2-en-1-yl)-5-[(prop-2-en-1-yl)sulfanyl]-4H-1,2,4-triazole

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