Synthesis of 1,2,4-triazoles as potential hypoglycemic agents

Blank, Benjamin; Nichols, D. M.; Vaidya, Praful D.

doi:10.1021/jm00276a040

Cited by 22 publications

(4 citation statements)

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“…High-resolution mass spectra (ESI-HRMS) were determined on an Agilent 6210 TOF instrument. 1 H NMR and 13 C NMR spectra were recorded on Varian Mercury Plus-400 spectrometer (400 and 100 MHz), δ in parts per million, J in Hertz, using TMS as internal standard.…”

Section: Methodsmentioning

confidence: 99%

“…On account of their unique structures and reactivities, 3-amino-2H-1,2,4-triazoles are widely utilised as intermediates to prepare various biologically important compounds, such as hypoglycemic agents, 1 [1,2,4]triazolo [1,5-a]pyrimidine bioactive derivatives, 2 tumour inhibitors [3][4][5][6] and selective inhibitors of TYK2 and JAK1 over JAK2 and JAK3. 7 1,2,4-Triazoles have an electron-rich bioisosteric ring that can mimic bioactive heterocyclic nuclei, such as imidazole, 8 pyrazole 9 and thiazole.…”

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confidence: 99%

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A Novel and Convenient Synthesis of 3-Amino-2H-1,2,4-Triazoles from Isoselenocyanates and Hydrazine Hydrate

Peng

Zhang

et al. 2018

Journal of Chemical Research

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A novel and convenient one-pot synthesis of 3-amino-2 H-1,2,4-triazoles from two molecules of isoselenocyanates and hydrazine hydrate via cyclodeselenisation was developed. Various 3-amino-2 H-1,2,4-triazoles were obtained in moderate to good yields (33–45%, based on isoselenocyanates). The selenium powder and aromatic amine side products during the reaction could be recycled for efficient preparation of isoselenocyanates, which improved the atom economy. A plausible mechanism was proposed for the formation of the target products.

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Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

A Novel and Convenient Synthesis of 3-Amino-2H-1,2,4-Triazoles from Isoselenocyanates and Hydrazine Hydrate

Peng

Zhang

et al. 2018

Journal of Chemical Research

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“…In addition, this nucleus can also coordinate with a variety of metal ions to generate organometallic compounds with diverse biological functions [23]. Several substituted 1,2,4-triazole compounds were reported to have interesting bioactivity as antimicrobial, antifungal [24], anti-tubercular [25], anti-inflammatory [26], antidiabetic [27], hypoglycaemic [28], anticonvulsant [29], antidepressant [30], anti-malarial [31], arthritis [32], anti-migraine [33], antiviral [34], antihypertensive [35,36], potassium channel activators [37], antileishmanial [38], antioxidant [39], and antiplatelet [40].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and X-ray Structure Analysis of the Polymeric [Ag2(4-Amino-4H-1,2,4-triazole)2(NO3)]n(NO3)n Adduct: Anticancer, and Antimicrobial Applications

El-Naggar,

Al-Rasheed,

AL-khamis

et al. 2023

Inorganics

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A new Ag(I) adduct was synthesized by the reaction of 4-amino-4H-1,2,4-triazole (L) with AgNO3. Its chemical structure was approved to be [Ag2(L)2(NO3)]n(NO3)n utilizing elemental analysis, FTIR spectra, and single crystal X-ray diffraction (SC-XRD). According to SC-XRD, there are two independent silver atoms which are coordinated differently depending on whether the nitrate anion is coordinated or not. The coordination geometry of Ag1 is a slightly bent configuration while Ag2 has a distorted tetrahedral structure. The 4-amino-4H-1,2,4-triazole ligand and one of the nitrate groups adopt bridging mode, which connects the crystallographically independent Ag1 and Ag2 atoms resulting in the formation of two-dimensional coordination polymer. Hirshfeld surface analysis displays that the intermolecular O···H (34.0%), Ag···N (10.6%), H···H (10.4%), Ag···O (9.3%), and N···H (9.0%) contacts are the most abundant interactions. Regarding anticancer activity, the [Ag2(L)2(NO3)]n(NO3)n demonstrates stronger cytotoxic efficacy against lung (IC50 = 3.50 ± 0.37 µg/mL) and breast (IC50 = 2.98 ± 0.26 µg/mL) carcinoma cell lines than the anticancer medication cis-platin. The [Ag2(L)2(NO3)]n(NO3)n complex showed interesting antibacterial and antifungal activities compared to the free components (AgNO3 and 4-amino-4H-1,2,4-triazole). The investigated silver(I) complex exhibits remarkable antibacterial activity against E. coli (MIC = 6.1 µg/mL) that may be on par with Gentamycin (MIC = 4.8 µg/mL). As a result, the newly synthesized Ag(I) complex could be suggested for anticancer and antibacterial treatments.

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“…During the last few decades, considerable attention has been devoted to synthesis of 1,2,4-triazole derivatives possessing such comprehensive bioactivities as antibacterial, antifungal (Karabasanagouda et al, 2007;Sztanke et al, 2008), antimycobacterial (Klimesová et al, 2004), anti-inflammatory (Mullican et al, 1993), analgesic (Tozkoparan et al, 2005), anticancer (Demirba et al, 2002), antihypertensive (Kakefuda et al, 2002), anticonvulsant (Küçükgüzel et al, 2004), antiviral (El-Essawy et al, 2008), antidepressant (Kane et al, 1988), antiasthmatic (Youichiro et al, 1996), diuretic (Mhasalkar et al, 1970) and hypoglycemic (Blank et al, 1972) activities.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of 4-amino-5-phenyl-4H-[1,2,4]-triazole-3-thiol derivatives as antimicrobial agents

Sahoo

Sharma

Pattanayak³

2009

Med Chem Res

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A series of novel 1,2,4-triazole derivatives have been synthesized by condensing the methyl benzoate and methyl salicylate with various substituents; their structures were established on the basis of elemental analysis, Fourier transform infrared spectroscopy (FTIR), 1 H nuclear magnetic resonance (NMR), and mass spectral data. All title compounds were subjected to in vitro antibacterial and antifungal screening against four different bacterial and fungal strains. Preliminary results indicate that some of them exhibit promising activities and deserve further consideration as potential antimicrobials.

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Synthesis of 1,2,4-triazoles as potential hypoglycemic agents

Cited by 22 publications

References 0 publications

A Novel and Convenient Synthesis of 3-Amino-2H-1,2,4-Triazoles from Isoselenocyanates and Hydrazine Hydrate

A Novel and Convenient Synthesis of 3-Amino-2H-1,2,4-Triazoles from Isoselenocyanates and Hydrazine Hydrate

Synthesis and X-ray Structure Analysis of the Polymeric [Ag2(4-Amino-4H-1,2,4-triazole)2(NO3)]n(NO3)n Adduct: Anticancer, and Antimicrobial Applications

Synthesis and evaluation of 4-amino-5-phenyl-4H-[1,2,4]-triazole-3-thiol derivatives as antimicrobial agents

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