An overview on the recent developments of 1,2,4-triazine derivatives as anticancer compounds

Cascioferro, Stella; Parrino, Barbara; Spanò, Virginia; Carbone, Anna; Montalbano, Alessandra; Barraja, Paola; Diana, Patrizia; Cirrincione, Girolamo

doi:10.1016/j.ejmech.2017.08.009

Cited by 101 publications

(100 citation statements)

References 105 publications

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“…N- 2,4-triazin-6-yl)phenyl]pivalamide (3) as a starting material, was obtained from acylated 6-(2 aminophenyl)-3-thioxo-1,2,4-triazin-5(4H)one (1) 14 with t-butoyl chloride in warming DMF, followed by hydrazinolysis in EtOH Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

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Behavior of 3-hydrazino-6-aryl-1,2,4-triazin-5-one as a strong nucleophile towards active electrophilic compounds and their antibacterial evaluation

Al-Romaizan¹

2019

Mediterr.J.Chem.,

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The behavior of 3-hydrazino-6-aryl-1,2,4-triazin-5-one towards the active electrophilic compounds in polar and/ or non-polar solvents and various times and temperatures, has been studied. N-[2-(3-(3/5-(4-Nitrophenyl)-5/3-thioxo-1H-1,2,4-triazol-1-yl)-5-oxo-1,2,4-triazin-6-yl)phenyl]pivalamides were obtained from the reaction of N-(2-(3-hydrazineyl-5-oxo-1,2,4-triazin-6-yl)phenyl)-pivalamide with 4-nitrobenzoyl isothiocyanate in THF and/ or EtOH-piperidine respectively. Also, N-(2-(3-hydrazineyl-5-oxo-1,2,4-triazin-6-yl)phenyl)-pivalamide was shown a strong nucleophilic behavior by reaction with N-phenyl-thiourea to produceÂ N-[2-(5-oxo-3-(2-(phenylcarbamothioyl)-hydrazineyl)-1,2,4-triazin-6-yl)phenyl]pivalamide, which upon cyclization with diethyl carbonate produced N-(2-(5-oxo-3-(5-oxo-4-phenyl-3-thioxo-1,2,4-triazolidin-1-yl)- 1,2,4-triazin-6-yl)phenyl)pivalamide. Moreover, N-(2-(3-hydrazineyl-5-oxo-1,2,4-triazin-6-yl)phenyl)pivalamide studied its behavior by reaction with cyanoacetic acid, chloroacetonitrile, and/ or benzoyl carbonitrile to produce N-(2-(3-amino-4,8-dioxo-4H-[1,2,4]triazino[4,3-b][1,2,4]triazin-7-yl)phenyl)pivalamide,N-(2-(4-amino-8-oxo-2H-[1,2,4]triazino[4,3-b][1,2,4]triazin-7-yl)phenyl)pivalamide and N-(2-(4-imino-8-oxo-3-phenyl-4H-[1,2,4] triazino [4,3-b][1,2,4]triazin-7-yl)phenyl)pivalamide. Structure of the products was established upon their elemental analysis and FT-IR, 1H/ 13C NMR, and MS. The new compounds were evaluated as antibacterial agents some Gram-positive and negative bacteria. Some compounds were showed the highest inhibition activity towards Pseudomonas aeruginosa, Bacillus subtilis, Bacillus cereus, and Sarcina lutea bacteria and lowest inhibitory activity against Escherichia coli bacteria.

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Section: Resultsmentioning

confidence: 99%

“…1). Moreover, the interaction between compound 3 as a strong nucleophile and cyanoacetic acid as bi-electrophile in ethanol with few drops of piperidine as a catalyst, yielded 11 (8), while treatment with 2-chloroacetonitrile in DMF, afforded 12 [1,2,4]triazin-7-yl)phenyl)pivalamide (9) respectively Scheme 4.…”

Section: Scheme 2 Synthesis Of Compounds 4 Andmentioning

confidence: 99%

Behavior of 3-hydrazino-6-aryl-1,2,4-triazin-5-one as a strong nucleophile towards active electrophilic compounds and their antibacterial evaluation

Al-Romaizan¹

2019

Mediterr.J.Chem.,

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“…Finally, the newly synthesized lamotrigine analogs (7)(8)(9)(10)(11)(12)(13)(14) were screened for their in vitro antibacterial activity against four bacterial isolated Bacillus subtilis, Streptococcus faecalis, Micrococcus luteus, and Staphylococcus aureus. The results of the study revealed that the compounds 7-14 showed significant antibacterial potency.…”

Section: Structures Of Lamotrigine Analogs 7-10mentioning

confidence: 99%

“…Recently, Makki et al 8,9 reported a simple route to synthesize Lamotrigine analogs as an antiinflammatory and antioxidant agent. 1,2,4-triazine nucleus is scaffold of various biological activities, also have a significant variety of pharmaceutical properties, such as antitumor 10 , anti-HIV, antimicrobial 11 . Also, isoxazole, 1,2,4-triazole, and benzo [d]imidazole cores have a significant role in towads bacteria [12][13][14] .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of some new 5-amino-3-(substituted-amino)-6-(fluoro/ nitro)aryl-1,2,4-triazine derivatives as lamotrigine analogs and their evaluation in vitro as antibacterial agents

Alharbi¹,

Alshammari

2019

Mediterr.J.Chem.,

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Some new fluorine-substituted 3,5-disubstituted amino-1,2,4-triazines have been obtained from aryl-amination of 2,2,2-trifluoro-N-[2-(5-hydroxy-3-thioxo-2,3-dihydro-1,2,4-triazin-6-yl)-4-nitrophenyl] acetamide followed by ammonolysis to produce N-(2-(5-amino-3-(arylamino)-1,2,4-triazin-6-yl)-4-nitrophenyl)-2,2,2-trifluoroacetamides which reacted with N-phenylthiourea. The structures of products were deduced from their elemental analysis and spectral measurements. The new lamotrigine analogs were evaluated in vitro as antibacterial. Interestingly, some compounds showed interesting activity against the Bacillus subtilis, Streptococcus faecalis, Micrococcus luteus, and Staphylococcus aureus bacteria.

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“…In addition, most of functionally 1,2,4-triazones form stable metal-complexes with metal ions [13]. Also, the reactivity of 3-thioxo-1,2,4-triazin-5-ones depends onto the active groups, International Journal of Organic Chemistry type of activation nature of substitution, leaving moities, character of nucleophile engaged, site selectivity and polarity of solvent used [14] [15] [16].…”

Section: Introductionmentioning

confidence: 99%

Various Routes to Synthesise 3-Thioxo-1,2,4-Triazine-5-One Derivatives as Antimicrobial Agents

Abdel‐Rahman¹,

Bawazir²

2018

IJOC

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A simple condensation afforded some new 3-thioxo-1,2,4-triazin-5-one derivatives (4, 6 and 8). Utilizing a facile condensation of (E)-4-(4'-bromo styryl)-2-oxo-3-buteneoic acid with thiosemicarbazide, dithioic formic acid hydrazide, and thiocarbahydrazide in different conditions. Structures of these compounds were confirmed by elemental and spectral analysis. The preliminary biocidal activity of these products were evaluated against some microbial and compared to Mycostatine and piperacillin as antibiotics were most of derivatives exhibited good activity.

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An overview on the recent developments of 1,2,4-triazine derivatives as anticancer compounds

Cited by 101 publications

References 105 publications

Behavior of 3-hydrazino-6-aryl-1,2,4-triazin-5-one as a strong nucleophile towards active electrophilic compounds and their antibacterial evaluation

Behavior of 3-hydrazino-6-aryl-1,2,4-triazin-5-one as a strong nucleophile towards active electrophilic compounds and their antibacterial evaluation

Synthesis of some new 5-amino-3-(substituted-amino)-6-(fluoro/ nitro)aryl-1,2,4-triazine derivatives as lamotrigine analogs and their evaluation in vitro as antibacterial agents

Various Routes to Synthesise 3-Thioxo-1,2,4-Triazine-5-One Derivatives as Antimicrobial Agents

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