Synthesis and Some Transformations of
5-(1,4-Benzodioxan-2-yl)-4-phenyl-4H-1,2,4-triazole-3-thiol

Vardanyan, S. O.; Avagyan, Ara; Aghekyan, A. A.; Sargsyan, A. B.; Harutyunyan, S. A.; Gasparyan, H. V.

doi:10.1134/s1070428020030112

Cited by 3 publications

(3 citation statements)

References 4 publications

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“…Using 5-(1,4-benzodioxan-2-yl)-4-phenyl-4H-1,2,4triazole-3-thiol (1) as initial compound, we previously obtained S-substituted derivatives containing phar maco phoric arylamidoalkyl groups, as well as N-aminomethyl derivatives with a piperidine or morpholine ring [5]. In continuation of these studies, herein we report the reaction of thiol 1 with acrylic acid and its derivatives, nitrile, amide, and ethyl ester, with the goal of obtaining new functionalized benzodioxanyl-substituted triazoles.…”

Section: Resultsmentioning

confidence: 99%

“…The progress of reactions and the purity of the isolated compounds were monitored by TLC on Silufol UV-254 plates using benzene (amides) or benzene-acetone (3:1; amines) as eluent; spots were visualized by treatment with iodine vapor. Initial 5-(1,4-benzodioxan-2-yl)-4-phenyl-4H-1,2,4triazole-3-thiol (1) was synthesized according to the procedure described in [5].…”

Section: Methodsmentioning

confidence: 99%

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Synthesis of N-Substituted Derivatives of 3-(1,4-Benzodioxan-2-yl)-4-phenyl-1,2,4-triazole-5(4H)-thiones

et al. 2021

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The addition of 5-(1,4-benzodioxan-2-yl)-4-phenyl-4H-1,2,4-triazole-3-thiol to the C=C double bond of acrylonitrile, acrylamide, and ethyl acrylate afforded 3-[3-(1,4-benzodioxan-2-yl)-4-phenyl-5-sulfanylidene-4,5-dihydro-1H-1,2,4-triazol-1-yl]propanoic acid nitrile, amide, and ethyl ester. The latter was converted to the corresponding hydrazide which reacted with substituted benzoyl chlorides to give unsymmetrical diacylhydrazines, and their cyclization by the action of phosphoryl chloride in toluene afforded tricyclic products containing 1,4-benzodioxane, 1,2,4-triazole, and 1,3,4-oxadiazole heterocycles.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Synthesis of N-Substituted Derivatives of 3-(1,4-Benzodioxan-2-yl)-4-phenyl-1,2,4-triazole-5(4H)-thiones

et al. 2021

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“…Human Aurora kinase B has an important role in the cell cycle and is overexpressed in tumor cells. The potential effects of the molecules on the targets were investigated using the web page: http://www.swisstargetprediction.ch/ [29][30][31][32][33][34]. Protein kinase B (Akt) plays a considerable role in signaling within cells as well as promoting both cell proliferation and survival, and in the case of cancer, this path is irregular.…”

Section: Molecular Dockingmentioning

confidence: 99%

Ultrasound Assisted Synthesis and In Silico Modelling of 1,2,4-Triazole Coupled Acetamide Derivatives of 2-(4-Isobutyl phenyl)propanoic acid as Potential Anticancer Agents

et al. 2022

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The development of an economical method for the synthesis of biologically active compounds was the major goal of this research. In the present study, we have reported the ultrasound-radiation-assisted synthesis of a series of novel N-substituted 1,2,4-triazole-2-thiol derivatives. The target compounds 6a–f were efficiently synthesized in significant yields (75–89%) by coupling 1,2,4-triazole of 2-(4-isobutylphenyl) propanoic acid 1 with different electrophiles using ultrasound radiation under different temperatures. The sonication process accelerated the rate of the reaction as well as yielded all derivatives compared to conventional methods. All derivatives were confirmed by spectroscopic (FTIR, 1HNMR, 13CNMR, HRMS) and physiochemical methods. All derivatives were further screened for their anticancer effects against the HepG2 cell line. Compound 6d containing two electron-donating methyl moieties demonstrated the most significant anti-proliferative activity with an IC50 value of 13.004 µg/mL, while compound 6e showed the lowest potency with an IC50 value of 28.399 µg/mL. The order of anticancer activity was found to be: 6d > 6b > 6f > 6a > 6c > 6e, respectively. The in silico modelling of all derivatives was performed against five different protein targets and the results were consistent with the biological activities. Ligand 6d showed the best binding affinity with the Protein Kinase B (Akt) pocket with the lowest ∆G value of −176.152 kcal/mol. Compound 6d has been identified as a promising candidate for treatment of liver cancer.

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Reaction of Perfluorobenzocyclobutene with Isomeric Tetrafluorobenzenes in an SbF5 Medium

et al. 2021

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Synthesis and Some Transformations of 5-(1,4-Benzodioxan-2-yl)-4-phenyl-4H-1,2,4-triazole-3-thiol

Cited by 3 publications

References 4 publications

Synthesis of N-Substituted Derivatives of 3-(1,4-Benzodioxan-2-yl)-4-phenyl-1,2,4-triazole-5(4H)-thiones

Synthesis of N-Substituted Derivatives of 3-(1,4-Benzodioxan-2-yl)-4-phenyl-1,2,4-triazole-5(4H)-thiones

Ultrasound Assisted Synthesis and In Silico Modelling of 1,2,4-Triazole Coupled Acetamide Derivatives of 2-(4-Isobutyl phenyl)propanoic acid as Potential Anticancer Agents

Reaction of Perfluorobenzocyclobutene with Isomeric Tetrafluorobenzenes in an SbF5 Medium

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