Synthesis and Antitumor Activity of New Substituted Mercapto‐1,2,4‐Triazine Derivatives, Their Thioglycosides, and Acyclic Thioglycoside Analogs

Nassar, Ibrahim F.

doi:10.1002/jhet.1022

Cited by 16 publications

(7 citation statements)

References 26 publications

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“…It is well known that derivatives of 1,2,4triazine-3-thione exhibit pesticide activity [1], as well as anticancer [2], psychotropic [3], and antiviral activity [4]. Annelated derivatives of triazines offer prom-ise in the field of drug development [5][6][7][8][9], in particular for neurodegenerative diseases [10].…”

Section: Introductionmentioning

confidence: 99%

Heterocyclization of 3-Propargylsulfanyl-5 Phenyl-1,2,4-Triazine: Tandem Reactions With Bromine Leading to New Derivatives of 7 Phenyl[1,3]thiazolo[3,2-B][1,2,4]triazinium

Rybakova

Kim

Данилина

et al. 2020

IVKKT

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Derivatives of 1,2,4-triazine-3-thione exhibit biological activity in a wide range. They have optoelectronic properties and can be used as synthons in synthesis of various pyridines by the Diels-Alder reaction. 1,2,4-Triazines are of the greatest interest, for organic synthesis in particular. In the present study we have established that the interaction of 3-propargylsulfanyl-5-phenyl-1,2,4-triazine, obtained by alkylation of 5-phenyl-2,3-dihydro-1,2,4-triazine-3-thione with 3-bromopropyne in acetone in the presence of triethylamine, with halogens leads to annelation of thiazole cycle. At that, [1,3]thiazolo[3,2-b][1,2,4]triazinium systems contain either endo- or exocyclic double bond in their structure, depending on the halogen type. By way of example, iodine acting on propargyl sulfide forms a dark precipitate of (3Z)-3-iodomethylene-7-phenyl-2,3-dihydro-[1,3]thiazolo[3,2-b][1,2,4]triazinium triiodide, the structure of which has been confirmed by 1H and 13C NMR spectroscopy, including two-dimensional 2D 1H-13C HSQC, HMBC and 1H-1H NOESY experiments. Treatment of the obtained triiodide by sodium iodide in acetone leads to synthesis of the corresponding monoiodide, which precipitates from the reaction mixture as a dark red precipitate. Reaction with bromine, as distinct from heterocyclization under iodine action, comprises an unusual cascade reaction including the stages of electrophile heterocyclization, bromine addition, and hydrogen bromide elimination, which leads to formation of 3-dibromomethyl-7-phenyl[1,3]thiazolo[3,2-b][1,2,4]triazinium bromide. It should be pointed out that the identifying feature of 3-propargylsulfanyl-5-phenyl-1,2,4-triazine heterocyclization under iodine and bromine action is the signal bias of the aromatic proton in a triazine ring towards weak field in the 1H NMR spectrum of the reaction products. This is presumably associated with formation of the positively charged nitrogen atom.

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Section: Introductionmentioning

confidence: 99%

Heterocyclization of 3-Propargylsulfanyl-5 Phenyl-1,2,4-Triazine: Tandem Reactions With Bromine Leading to New Derivatives of 7 Phenyl[1,3]thiazolo[3,2-B][1,2,4]triazinium

Rybakova

Kim

Данилина

et al. 2020

IVKKT

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“…Furthermore, some pyrazolo[3,4‐ d ]pyrimidine derivatives manifested significant activity as anti‐inflammatory agents . We have been aiming in this work to synthesize some new substituted heterocyclic systems on the basis of pyrazole moiety of expected biological interest and to test them as biodegradable agrochemicals .…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Anticancer Activity of Some New Fused Pyrazoles and Their Glycoside Derivatives

Nassar

Farargy

Abdelrazek

2018

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).4-(4-Chlorobenzylidene)-2,5-diphenyl-2,3-dihydro-3H-pyrazol-3-one 3a and 4-(3,4-dimethoxybenzylidene)-5-phenyl-2,3-dihydro-3H-pyrazol-3-one 3b were prepared and were reacted with phenylhydrazine, thiosemicarbazide, hydroxylamine hydrochloride, ethyl acetoacetate, diethylmalonate, malononitrile, ethyl cyanoacetate, and thiourea yielding fused pyrazole derivatives. Some of the new compounds were reacted with cyclic and acyclic sugars to produce new S-, O-, and N-glycoside derivatives. The antitumor activity against the human breast cancer cells (MCF-7) was assessed. Four of the new compounds showed IC 50 values less than those of the positive control, indicating that these four compounds are better anticancer agents than doxorubicin.

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“…6-Aza analogues of the naturally occurring nucleic acids components represent isosteres with the C-6 carbon atom of the pyrimidine nucleoside base being replaced by nitrogen. 7,8 Certain azanucleosides, 6-azauracil and 6-azacytosine), structurally based on 1,2,4-triazine nucleus have displayed an impressive array of biological activities, among which antitumor, [9][10][11][12][13][14][15][16][17][18][19] antiviral, 20 antimicrobial, 21 antiinflammatory, 22 antiplatelet, 23 antimalarial, 24 and antifungal 25 properties. Additionally, tertiary amines in the linkers reported to be positively charged at physiological pH in order to favor electrostatic interactions in the minor groove with the anionic phosphate DNA backbone.…”

Section: Introductionmentioning

confidence: 99%

In vitro antitumor activity evaluation of some 1,2,4-triazine derivatives bearing piperazine amide moiety against breast cancer cells

Yurttaş

Demirayak

Ilgın

et al. 2014

Bioorganic & Medicinal Chemistry

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Synthesis and Antitumor Activity of New Substituted Mercapto‐1,2,4‐Triazine Derivatives, Their Thioglycosides, and Acyclic Thioglycoside Analogs

Cited by 16 publications

References 26 publications

Heterocyclization of 3-Propargylsulfanyl-5 Phenyl-1,2,4-Triazine: Tandem Reactions With Bromine Leading to New Derivatives of 7 Phenyl[1,3]thiazolo[3,2-B][1,2,4]triazinium

Heterocyclization of 3-Propargylsulfanyl-5 Phenyl-1,2,4-Triazine: Tandem Reactions With Bromine Leading to New Derivatives of 7 Phenyl[1,3]thiazolo[3,2-B][1,2,4]triazinium

Synthesis and Anticancer Activity of Some New Fused Pyrazoles and Their Glycoside Derivatives

In vitro antitumor activity evaluation of some 1,2,4-triazine derivatives bearing piperazine amide moiety against breast cancer cells

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