Journal articles: '5-triazine'

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Egorov, Ilya N., Igor S. Kovalev, Vladimir L. Rusinov, and Oleg N. Chupakhin. "Cyclotrimerization of 3-R-1,2,4-Triazin-5(4H)-ones with Cyclic Ketones." Zeitschrift für Naturforschung B 65, no. 11 (2010): 1359–62. http://dx.doi.org/10.1515/znb-2010-1111.

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New heterocyclic tetracyclic systems were synthesized. Interaction between 3-R-1,2,4-triazin- 5(4H)-ones and cyclic ketones under acidic conditions leads to the formation of zwitterion derivatives of 5,6,7,8,9,10,11,12-octahydro-[1,2,4]triazino[1,6- ƒ ]phenanthridine and 1,2,3,6,7,8-hexahydro-bicyclopenta[ b,d]pyrido[1,2- ƒ ][1,2,4]triazine.

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Jain, Sonika, Pankaj Kumar Jain, Shalu Sain, Dharma Kishore, and Jaya Dwivedi. "Anticancer s-Triazine Derivatives: A Synthetic Attribute." Mini-Reviews in Organic Chemistry 17, no. 8 (2020): 904–21. http://dx.doi.org/10.2174/1570193x17666200131111851.

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1, 3, 5-Triazine (s-Triazine) is a versatile nucleus to design and develop potent bioactive molecules for drug discovery, particularly in cancer therapy. The aim of this review is to present the most recent trends in the field of synthetic strategies made for functionalized triazine derivatives active against cell proliferation. This review article covers the synthesis of aryl methylamino, morpholino, triamino substituted triazines, antimitotic agents coupled triazines and many more. Many 1,3,5- triazine derivatives, both hetero-fused and uncondensed, have shown remarkable antitumor activities. We have highlighted various derivatives with 1, 3, 5-triazine core targeting different kinases with an aim to help researchers for developing new 1, 3, 5-triazine derived compounds for antitumor activity.

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Protas, A. V., O. V. Mikolaichuk, E. A. Popova, et al. "Functionalized 1,3,5-triazine-derivatives as promising anticancer agents: synthesis and cytotoxic activity in vitro." Scientific Notes of the Pavlov University 31, no. 1 (2024): 55–61. http://dx.doi.org/10.24884/1607-4181-2024-31-1-55-61.

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Introduction. A promising area of application of 1,3,5-triazines in medical chemistry is the development of highly effective anticancer agents. It is noteworthy that a significant cytotoxic effect may occur with 2,4,6-substituted 1,3,5-triazine derivatives containing aziridine rings as substituents. These compounds interact with DNA molecules of tumor cells and they are alkylating agents.The objective was to synthesize and investigate the cytotoxic activity in vitro of new aziridine–containing 1,3,5-triazine derivatives against tumor cell lines of human lung adenocarcinoma A549 and human hepatocarcinoma Huh7 and to evaluate the effect of the length of the hydrocarbon radical in the dioxane cycle on the cytotoxic effect of the obtained compounds.Methods and materials. The synthesis of the 1,3,5-triazine derivatives was carried out using 2,4,6-trichloro-1,3,5-triazine (cyanuric chloride) as the starting reagent. The composition and structure of the obtained compounds were proven by elemental CHN analysis and 1H, 13C{1H} NMR spectroscopy. The cytotoxicity was studied using the MTT colorimetric assay.Results. Novel 1,3,5-triazine derivatives were synthesized and fully characterized: (5-((4-(aziridin-1-yl)-6-chloro-1,3,5triazin-2-yl)amino)-2-ethyl-2-methyl-1,3-dioxan-5-yl)methanol and (5-((4-(aziridin-1-yl)-6-chloro-1,3,5-triazin-2-yl)amino)2-isobutyl-2-methyl-1,3-dioxan-5-yl)methanol. Also, cytotoxic effect against tumor cell lines of human lung adenocarcinoma (A549) and human hepatocarcinoma (Huh7) was studied using the MTT assay. It has been shown that an increase in the length of hydrocarbon radicals in the dioxane ring at position C2 leads to a decrease in cytotoxic effect.Conclusion. The synthesized (5-((4-(aziridin-1-yl)-6-chloro-1,3,5-triazin-2-yl)amino)-2-ethyl-2-methyl-1,3-dioxane-5 -yl) methanol and (5-((4-(aziridin-1-yl)-6-chloro-1,3,5-triazin-2-yl)amino)-2-isobutyl-2-methyl-1,3-dioxan-5-yl)methanol cause a dose-dependent decrease against the survival of tumor cell lines A549 and Huh7.

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Jacobsen, NW, and AE Philippides. "Heterocyclic Variants of the Purine System. I. Derivatives of Thiazolo[5,4-e]-1,2,4-Triazine." Australian Journal of Chemistry 40, no. 3 (1987): 491. http://dx.doi.org/10.1071/ch9870491.

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Derivatives of the thiazolo [5,4-e]-1,2,4-triazine ring system were prepared from appropriate 6-acylamino-1,2,4-triazin-5(2H)-ones by thiation and cyclization with phosphorus pentasulfide. 5-Methylthio-1,2,4-triazin-6-amines also gave thiazolo [5,4-e]-1,2,4-triazine derivatives when treated with carbon disulfide or phenyl isothiocyanate.

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Ducruet, Jean-Marc, Sophie Creuzet, and Josiane Viénot. "Kinetics of Action of Different Photosystem II Herbicides on Thylakoids." Zeitschrift für Naturforschung C 45, no. 5 (1990): 348–52. http://dx.doi.org/10.1515/znc-1990-0507.

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The kinctics of inhibition of photosystem II electron transfer by different diuron-like herbicides (ureas, triazines, triazinoncs, biscarbamates. uraciles) were studied, mainly by chlorophyll fluorescence measurements. Uracil derivatives and cyanazine, a particular triazinc. were the slowest acting compounds. The half-times of action were strongly temperature-dependent and were of the order of tens of seconds at 5 °C for urea or triazine inhibitors. The role of different limiting steps in the binding process is discussed.

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Krinochkin, A. P., E. D. Ladin, Ya K. Shtaitz, et al. "Interaction of 1,2,4-triazine-5-carbonitriles with 5-hydroxyethylsulfanyl- and 5-hydroxyethoxyethylsulfanyl-3-amino-1,2,4-triazoles." Журнал органической химии 59, no. 11 (2023): 1501–6. http://dx.doi.org/10.31857/s0514749223100137.

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The solvent-free interaction of 1,2,4-triazine-5-carbonitriles with first synthesized 5-hydroxyethylsulfanyland 5-hydroxyethoxyethylsulfanyl-3-amino-1,2,4-triazoles at heating has been studied. It was shown that the presence of these substituents at the C5 position of 1,2,4-triazole changes the direction of the reaction, and 5-amino-1,2,4-triazines are formed as the main products, while the products of the ipso -substitution of the C5-cyano group containing the moiety of the substituted 1,2,4-triazole were isolated only as by-products. In the case of using 1,2,4-triazole with a fragment of monoethylene glycol at C5 position of triazine, the formation of a complex mixture of products occurred.

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Tan, Ri Hong. "Synthesis and Biological Activities of 1,2,4-Triazine Derivatives." Advanced Materials Research 1033-1034 (October 2014): 283–86. http://dx.doi.org/10.4028/www.scientific.net/amr.1033-1034.283.

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To sdudy the synthesis and biological activities of 1,2,4-triazine derivatives, a series of 1,2,4-triazines were prepared from the reaction of 3-mercapto-5-hydroxyl-6-methyl-1,2,4-triazine with alkyl halide.The structures of prepared compounds were confirmed by IR,1H-NMR and elemental analysis. Biological activities showed the compounds had anti-inflammatory activities.

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Mykolaichuk, O. V., A. V. Protas, E. A. Popova, et al. "Synthesis and study of some properties of new tetrazole-containing derivatives of morpholin-4-yl-1,3,5-triazine and 4-methylpiperidin-1-yl-1,3,5-triazine." Журнал общей химии 93, no. 5 (2023): 695–710. http://dx.doi.org/10.31857/s0044460x23050050.

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New tetrazole-containing derivatives of morpholin-4-yl-1,3,5-triazine and 4-methylpiperidin-1-yl-1,3,5-triazine were synthesized. Cytotoxic activity of the compounds obtained against human liver tumor cell lines Huh-7 and human lung A549 was studied by the MTT test. It was shown that these substances do not exhibit a pronounced cytotoxic effect. The most significant antitumor activity was shown by 1,3,5-triazine containing 5-phenyltetrazol-2-ylacetohydrazide fragment and 4-methylpiperidine ring as substituents, as well as 1,3,5-triazine containing 5-methyl-1 H -tetrazol-1-ylacetohydrazide fragment and two morpholine rings. For these compounds, the interaction with DNA was studied by UV spectroscopy. For N ’-(4,6-dimorpholino-1,3,5-triazin-2-yl)-2-(5-methyl-1 H -tetrazol-1-yl)acetohydrazide, the DNA binding constant was determined ( K bin 9.02× 104 M.-1) and studied the ability to inhibit the tyrosine kinase domain of surface receptors. It was shown that the studied tetrazole-containing derivatives of 1,3,5-triazine do not exhibit antioxidant properties with respect to NO-radicals and do not cause photoinduced hemolysis.

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Krinochkin, A. P., A. Rammohan, D. S. Kopchuk, et al. "TRANSFORMATIONS OF 5-HYDRAZINYL-1,2,4-TRIAZINES IN THE REACTION WITH 2,5-NORBORNADIENE." Доклады Российской академии наук. Химия, науки о материалах 508, no. 1 (2023): 50–54. http://dx.doi.org/10.31857/s268695352260026x.

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The interaction between 5-hydrazinyl-substituted 1,2,4-triazines and 2,5-norbornadiene at elevated temperature and pressure (in autoclave) have been studied. The 2-aminopyridines, 5-amino-1,2,4-triazines and 6-unsubstituted pyridines are the products of this reaction. The formation of last two products depends on the substituent at C3 position of the triazine.

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Jacobsen, NW, and AE Philippides. "Heterocyclic Variants of the Purine System. II. Derivatives of Thiazolo[4,5-E]-1,2,4-Triazines, a New Heterocyclic Ring System." Australian Journal of Chemistry 40, no. 4 (1987): 693. http://dx.doi.org/10.1071/ch9870693.

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.Some representative derivatives of the new thiazolo [4,5- e]-1,2,4-triazine ring system were prepared from 5-acylamino-1,2,4-triazin-6(1 H)-ones by heating with phosphorus pentasulfide in pyridine. Further derivatives of the biheterocyclo system were also made from 6-methylthio-1,2,4-triazin-5-amines by heating with carbon disulfide or phenyl isothiocyanate.

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Jeon, Youngeun, Jineun Kim, Gihang Kang, and Tae Ho Kim. "Crystal structure of anilazine." Acta Crystallographica Section E Structure Reports Online 70, no. 9 (2014): o923. http://dx.doi.org/10.1107/s160053681401647x.

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The title compound [systematic name: 4,6-dichloro-N-(2-chlorophenyl)-1,3,5-triazin-2-amine], C9H5Cl3N4, is a triazine fungicide. The dihedral angle between the planes of the triazine and benzene rings is 4.04 (8)°. In the crystal, two weak C—H...N hydrogen bonds and short Cl...Cl contacts [3.4222 (4) Å] link adjacent molecules, forming two-dimensional networks parellel to the (112) plane. The planes are linked by weak intermolecular π–π interactions [3.6428 (5) and 3.6490 (5) Å], resulting in a three-dimensional architecture.

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Fuerst, E. Patrick, Charles J. Arntzen, Klaus Pfister, and Donald Penner. "Herbicide Cross-Resistance in Triazine-Resistant Biotypes of Four Species." Weed Science 34, no. 3 (1986): 344–53. http://dx.doi.org/10.1017/s0043174500066960.

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The cross-resistance of triazine-resistant biotypes of smooth pigweed (Amaranthus hybridusL. # AMACH), common lambsquarters (Chenopodium albumL. # CHEAL), common groundsel (Senecio vulgarisL. # SENVU), and the crop canola (Brassica napusL. var. Atratower) to a selection of herbicides was evaluated at both the whole plant and chloroplast level. The triazine-resistant biotypes of all four species showed a similar pattern of cross-resistance, suggesting that a similar mutation had occurred in each species. The four triazine-resistant biotypes were resistant to injury from atrazine [6-chloro-N-ethyl-N′-(1-methylethyl)-1,3,5-triazine-2,4-diamine], bromacil [5-bromo-6-methyl-3-(1-methylpropyl)-2,4-(1H,3H)pyrimidinedione], and pyrazon [5-amino-4-chloro-2-phenyl-3(2H)-pyridazinone] and were slightly resistant to buthidazole {3-[5-(1,1-dimethylethyl)-1,3,4-thiadiazol-2-yl]-4-hydroxy-1-methyl-2-imidazolidinone}. The triazine-resistant biotypes were more sensitive to dinoseb [2-(1-methylpropyl)-4,6-dinitrophenol]. Triazine-resistant smooth pigweed showed resistance to cyanazine {2-[[4-chloro-6-(ethylamino)-1,3,5-triazin-2-yl] amino]-2-methylpropanenitrile} and metribuzin [4-amino-6-(1,1-dimethylethyl)-3-(methylthio)-1,2,4-triazin-5(4H)-one] with slight resistance to linuron [N′-(3,4-dichlorophenyl)-N-methoxy-N-methylurea] and desmedipham {ethyl [3-[[(phenylamino)carbony] oxy] phenyl] carbamate}. There was little or no resistance to diuron [N′-(3,4-dichlorophenyl)-N,N-dimethylurea], bromoxynil (3,5-dibromo-4-hydroxybenzonitrile), bentazon [3-(1-methylethyl)-(1H)-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide], or dicamba (3,6-dichloro-2-methoxybenzoic acid). Parallel studies at the chloroplast level indicated that the degree of resistance to inhibition of photosynthetic electron transport was highly correlated with the degree of resistance to herbicidal injury. This correlation indicates that atrazine, cyanazine, metribuzin, pyrazon, bromacil, linuron, desmedipham, and buthidazole cause plant injury by inhibition of photosynthesis. This correlation also indicates that triazine resistance and cross-resistance at the whole plant level is due to decreased sensitivity at the level of photosynthetic electron transport. Cross-resistance to numerous additional herbicides was evaluated on isolated chloroplast thylakoid membranes and these results are discussed.14C-atrazine was displaced from thylakoid membranes by several herbicides, indicating that these herbicides compete for a common binding site.

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Moreno, Leydi, Jairo Quiroga, Rodrigo Abonia, Jonathan Ramírez-Prada, and Braulio Insuasty. "Synthesis of New 1,3,5-Triazine-Based 2-Pyrazolines as Potential Anticancer Agents." Molecules 23, no. 8 (2018): 1956. http://dx.doi.org/10.3390/molecules23081956.

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A new series of 1,3,5-triazine-containing 2-pyrazoline derivatives (8–11)a–g was synthesized by cyclocondensation reactions of [(4,6-bis((2-hydroxyethyl)amino)-1,3,5-triazin-2-yl)amine]chalcones 7a–g with hydrazine hydrate and derivatives. Chalcones 7a–g were obtained by Claisen-Schmidt condensation between aromatic aldehydes and triazinic derivative 5, which was synthesized in high yield by a microwave-assisted reaction. Seventeen of the synthesized compounds were selected and tested by the US National Cancer Institute (NCI) for their anticancer activity against 58 different human tumor cell lines. Compounds 7g and 10d,e,g showed important GI50 values ranging from 0.569 to 16.6 µM and LC50 values ranging from 5.15 to >100 µM.

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Fuerst, E. Patrick, Michael Barrett, and Donald Penner. "Control of Triazine-Resistant Common Lambsquarters (Chenopodium album) and Two Pigweed Species (Amaranthusspp.) in Corn (Zea mays)." Weed Science 34, no. 3 (1986): 440–43. http://dx.doi.org/10.1017/s0043174500067151.

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Various chemical treatments were evaluated over two growing seasons for control of triazine-resistant common lambsquarters (Chenopodium albumL. # CHEAL) and for control of a triazine-resistant infestation containing both redroot pigweed (Amaranthus retroflexusL. # AMARE) and Powell amaranth (A. powelliiS. Wats. # AMAPO). Atrazine [6-chloro-N-ethyl-N′-(1-methylethyl)-1,3,5-triazine-2,4-diamine], cyanazine {2-[[4-chloro-6-(ethylamino)-1,3,5-triazin-2-yl] amino]-2-methylpropanenitrile}, and metribuzin [4-amino-6-(1,1-dimethylethyl)-3-(methylthio)-1,2,4-triazin-5(4H)-one] provided unsatisfactory control of these biotypes. Satisfactory control of common lambsquarters was obtained with preemergence applications of pendimethalin [N-(1-ethylpropyl)-3,4-dimethyl-2,6-dinitrobenzenamine] or dicamba (3,6-dichloro-2-methoxybenzoic acid), or postemergence applications of dicamba, bromoxynil (3,5-dibromo-4-hydroxybenzonitrile), or bentazon [3-(1-methylethyl)-(1H)-2,1,3-benzothiadiazin-4(3H)-one 2,2-dioxide]. Satisfactory control of pigweed was obtained with preemergence applications of alachlor [2-chloro-N-(2,6-diethylphenyl)-N-(methoxymethyl)acetamide] or postemergence treatments of dicamba, bromoxynil, or 2,4-D [(2,4-dichlorophenoxy) acetic acid].

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Wamhoff, Heinrich, and Milena Tzanova. "Novel 6-Azapteridines from Bifunctional 1,2,4-Triazines." Collection of Czechoslovak Chemical Communications 68, no. 5 (2003): 965–74. http://dx.doi.org/10.1135/cccc20030965.

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The convergent synthesis of ethyl 5-chloro- and 5-amino-3-aryl-1,2,4-triazinecarboxylates 9a-9d and 10a-10d as well as of 5-amino-3-aryl-1,2,4-triazine-6-carboxamides 11a-11d is described. Compounds 9, 10 and 11 are powerful key compounds for cyclization reactions to the novel pyrimido[4,5-e][1,2,4]triazines 13d, 14c, 14d, 15c and 17a, 17d.

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Deohate, Pradip P., and Roshani S. Mulani. "Microwave Irradiative Synthesis of Triazine Substituted Pyrazoles and Study of Antitubercular and Antimicrobial Activities." Asian Journal of Chemistry 31, no. 5 (2019): 1087–90. http://dx.doi.org/10.14233/ajchem.2019.21826.

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Microwave irradiative synthesis of triazine substituted pyrazoles i.e. (4-benzylideneamino-6-methyl-[1,3,5]-triazin-2-yl)-(5-methyl-2-substituted benzoyl/isonicotinoyl/cinnamoyl-pyrazol-3-yl)-amines have been achieved by the cyclocondensation of N-(4-benzylideneamino-6-methyl-[1,3,5]-triazin-2-yl)-3-oxo butyramide with substituted acid hydrazides. Synthesis of required butyramide was done by reacting 2,4-diamino-6-methyl-[1,3,5]-triazine with benzaldehyde and then condensing the product with ethyl acetoacetate. Structural investigation of synthesized compounds has been done by chemical transformation, elemental analysis and IR, 1H NMR, mass spectral studies. Study of antitubercular and antimicrobial activity of title compounds against some selected Gram-positive and Gram-negative microorganisms was performed to establish the relationship between structure and activity of compound.

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Ducruet, Jean-M. arc, and René Scalla. "Action of Methylthiopyrimidine Experimental Herbicides as Diuron-Like Inhibitors of Photosynthesis." Zeitschrift für Naturforschung C 40, no. 5-6 (1985): 388–90. http://dx.doi.org/10.1515/znc-1985-5-617.

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Abstract Derivatives of 6-chloro-5-methylthiopyrimidines provide potent inhibitors of the photosynthetic electron flow, which act like Diuron on fluorescence induction kinetics and competitively displace it from its binding site. Structure-activity relationships show that, unlike triazines, activities of 2-or 4-alkylamino derivatives are restricted by steric hindrances. Decreases in inhibitory activities of these compounds observed in triazine-resistant chloroplasts are lower than decreases reported for triazines themselves.

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Wen, Li-Rong, Jian-Xia Zhou, and Peng Liu. "5-Phenyl-3-[3-(5-phenyl-1,2,4-triazin-3-ylsulfanyl)propylsulfanyl]-1,2,4-triazine." Acta Crystallographica Section E Structure Reports Online 62, no. 10 (2006): o4704—o4705. http://dx.doi.org/10.1107/s1600536806038682.

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Santra, Sougata, Dmitry Kopchuk, Alexey Krinochkin, et al. "An Efficient Cyanide-Free Approach towards 1-(2-Pyridyl)isoquinoline-3-carbonitriles via the Reaction of 5-Phenacyl-1,2,4-triazines with 1,2-Dehydrobenzene in the Presence of Alkyl Nitrites." Synlett 29, no. 04 (2017): 483–88. http://dx.doi.org/10.1055/s-0036-1590961.

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A cyanide-free method for the preparation of 1-(2-pyridyl)isoquinoline-3-carbonitriles (3-cyanoisoquinolines) was developed. The interaction of 5-phenacyl-3-(2-pyridyl)-1,2,4-triazines with 1,2-dehydrobenzene generated in situ from anthranilic acid and an excess of amyl nitrites afforded the target compounds in good yields. The proposed mechanism involves the in situ transformation of the 5-phenacyl group into the 5-cyano group under the action of alkyl nitrite and the following inverse demand aza-Diels–Alder reaction of thus formed 5-cyano-1,2,4-triazines with 1,2-dehydrobenzene affording the target products. The presence of the 5-phenacyl substituent is a key for the reaction, as in case of 5-styryl- or 5-phenylethynyl-3-(2-pyridyl)-1,2,4-triazines the formation of the 1,2,4-triazine ring-transformation products was observed

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Latacz, Gniewomir, Annamaria Lubelska, Magdalena Jastrzębska-Więsek, et al. "The 1,3,5-Triazine Derivatives as Innovative Chemical Family of 5-HT6 Serotonin Receptor Agents with Therapeutic Perspectives for Cognitive Impairment." International Journal of Molecular Sciences 20, no. 14 (2019): 3420. http://dx.doi.org/10.3390/ijms20143420.

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Among serotonin receptors, the 5-HT6 subtype is the most controversial and the least known in the field of molecular mechanisms. The 5-HT6R ligands can be pivotal for innovative treatment of cognitive impairment, but none has reached pharmacological market, predominantly, due to insufficient “druglikeness” properties. Recently, 1,3,5-triazine-piperazine derivatives were identified as a new chemical family of potent 5-HT6R ligands. For the most active triazine 5-HT6R agents found (1–4), a wider binding profile and comprehensive in vitro evaluation of their drug-like parameters as well as behavioral studies and an influence on body mass in vivo were investigated within this work. Results indicated the most promising pharmacological/druglikeness profiles for 4-((1H-indol-3-yl)methyl)-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-amine (3) and 4-((2-isopropyl-5-methylphenoxy)methyl)-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-amine (4), which displayed a significant procognitive action and specific anxiolytic-like effects in the behavioral tests in vivo together with satisfied pharmaceutical and safety profiles in vitro. The thymol derivative (4) seems to be of higher importance as a new lead candidate, due to the innovative, non-indole and non-sulfone structure with the best 5-HT6R binding properties.

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Wang, Tairan, Jixun Gong, and Chunyang Jia. "All-in-one Dual-Band Wide Optical Modulation Electrochromic Films." Highlights in Science, Engineering and Technology 126 (January 10, 2025): 98–102. https://doi.org/10.54097/efhxgc89.

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The electron-withdrawing property of the six-unit ring containing three nitrogen atoms in the structure of 2, 4, 6-tris (4-pyridyl)1,3,5-triazine was utilized to form with bipyridine salts two new viologen derivatives, 4, 4', 4''- (1, 3, 5-triazin-2, 4, 6-triyl) tris -1- (but-3-enyl) pyridine) (TPBET) and 4, 4', 4''- (1, 3, 5-triazine-2, 4, 6-triyl) tris 1-(4-vinylbenzylpyridine) (TPSET) were prepared as electrochromic devices (ECDs) with dual-band wide optical modulation. The maximum transmittance modulation of the prepared ECDs in the visible/near-infrared bands reaches 82.46 % and 78.31 %, respectively, and its good stability enables it to maintain the initial transmittance modulation range of 91.6 % after 1,000 cycles, which brings a good prospect for the application of electrochromic smart windows.

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Valieva, M. I., A. Rammohan, E. S. Starnovskaya, et al. "Reactions of 5-(1,2-dicarbadodecaboran-1-yl)-3-(2-pyridyl)1,2,4-triazines with dienophiles." Журнал общей химии 93, no. 3 (2023): 379–84. http://dx.doi.org/10.31857/s0044460x2303006x.

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The reactions of 5-(1,2-dicarbadodecaboran-1-yl)-3-(2-pyridyl)-1,2,4-triazines with various dienophiles (2,5-norbornadiene, 1-morpholinocyclopentene, 1,2-dehydrobenzene, and 2-amino-4-phenyloxazole) were studied. It was shown that the presence of a carborane fragment in the 1,2,4-triazine ring causes an atypical reaction with dienophiles without the formation of the expected aza -Diels-Alder reaction products except for the reaction with 2,5-norbornadiene. The reaction of 5-(1,2-dicarbadodecaboran-1-yl)-3-(2-pyridyl)-1,2,4triazines with 2-amino-4-phenyloxazole unexpectedly led to the formation of the corresponding 4,5-dihydro1,2,4-triazines. One of the previously described procedures for the direct introduction of a carborane residue into the C5 position of 1,2,4-triazines was optimized.

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Jacobsen, NW, and SE Rose. "1,2,4-Triazines. 1. The Use of C-13 Nuclear-Magnetic-Resonance Spectroscopy to Determine the Methylation Products of 3-Methylthio-1,2,4-Triazin-5(2h)-One." Australian Journal of Chemistry 38, no. 12 (1985): 1809. http://dx.doi.org/10.1071/ch9851809.

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Carbon-13 nuclear magnetic resonance spectroscopy utilizing both proton coupled and decoupled spectra has been found to be a useful method to determine unequivocally the sites of methylation in the 1,2,4-triazine series. Specifically, the method identified the methylation products of 3-methylthio-1,2,4-triazin-5(2H)-one as the new zwitterion 1-methyl-3- methylthio-1,2,4-triazinium-5-olate and the previously reported N2, N4- and O-methyl isomers.

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Rybakova, Anastasiya V., Dmitry G. Kim, Elena I. Danilina, Olesya V. Sazhaeva, Marina A. Ezhikova, and Mikhail I. Kodess. "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." IZVESTIYA VYSSHIKH UCHEBNYKH ZAVEDENII KHIMIYA KHIMICHESKAYA TEKHNOLOGIYA 63, no. 6 (2020): 19–24. http://dx.doi.org/10.6060/ivkkt.20206306.6102.

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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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Łażewska, Dorota, Małgorzata Więcek, Grzegorz Satała, et al. "New Triazine Derivatives as Serotonin 5-HT6 Receptor Ligands." Molecules 28, no. 3 (2023): 1108. http://dx.doi.org/10.3390/molecules28031108.

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Since the number of people with Alzheimer’s disease (AD) continues to rise, new and effective drugs are urgently needed to not only slow down the progression of the disease, but to stop or even prevent its development. Serotonin 5-HT6 receptor (5-HT6R) ligands are still a promising therapeutic target for the treatment of AD. 1,3,5-Triazine derivatives, as novel structures lacking an indole or a sulfone moiety, have proven to be potent ligands for this receptor. In present work, new derivatives of the compound MST4 (4-((2-isopropyl-5-methylphenoxy)methyl)-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-amine), the potent 5-HT6R antagonist (Ki = 11 nM) with promising ADMET and in vivo properties, were designed. The synthesized compounds were tested for their affinity towards 5-HT6R and other receptor (off)targets (serotonin 5-HT2A, 5-HT7 and dopamine D2). Based on the new results, 4-(2-tert-butylphenoxy)-6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-amine (3) was selected for extended in vitro studies as a potent and selective 5-HT6R ligand (Ki = 13 nM). Its ability to permeate the blood–brain barrier (BBB) and its hepatotoxicity were evaluated. In addition, X-ray crystallography and solubility studies were also performed. The results obtained confirm that 6-(4-methylpiperazin-1-yl)-1,3,5-triazin-2-amine derivatives, especially compound 3, are promising structures for further pharmacological studies as 5-HT6R ligands.

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26

Ali, Ola Ahmad Abu. "Synthesis and Characterization Antifungal Fluorine Substituted Fused Heterobicyclic Nitrogen Systems Containing 1,2,4-triazine Moiety." Journal of Molecular Biology Research 8, no. 1 (2018): 41. http://dx.doi.org/10.5539/jmbr.v8n1p41.

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Synthesis of some new full fluorinated heterobicyclic nitrogen systems containing 1,2,4-triazine moiety (4-10) have been deduced from heterocyclization of 6-(2'-trifluoroacetylamino)phenyl-3-(4'-fluorophenyl-1,2,4-triazin-5-one (3) with active oxo / halo-compounds. Structure of the products have been established upon their elemental and spectral date. Most of these systems exhibited a good to moderate antifungal activities.

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27

Verma, Tarawanti, Manish Sinha, and Nitin Bansal. "Synthesis of Novel 1,2-Dihydro-1,2,4-Triazin-6(5H)-one Derivatives as Anticancer Agents." Current Bioactive Compounds 16, no. 7 (2020): 1116–31. http://dx.doi.org/10.2174/1573407215666191022123310.

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Introduction: Cancer is still an untreatable disease and the second leading cause of death globally. The heterocyclic compounds have always played a major role in the anticancer drug discovery program. 1,2,4-Triazine-6-ones is a heterocyclic privileged structure with diversified activities. In the presented study, 21 novel 2,5-disubstituted-3-phenyl-1,2-dihydro-1,2,4-triazin-6 (5H)-one derivatives (13(a-k), 18(a-j) and 21(a1-a4, b)) have been synthesized and tested for their anticancer activity. Methods: The 2,5-disubstituted-3-phenyl-1,2-dihydro-1,2,4-triazin-6(5H)-one derivatives (13(a-k), 18(a-j) and 21(a1-a4, b) were synthesized by refluxing substituted-2-phenyloxazol-5(4H)-one and hydrazine derivatives. Substituted aldehydes were synthesized via Vilsmeier-Haack reaction, while substituted- 2-phenyloxazol-5(4H)-one derivatives were synthesized by Erlenmeyer Plochl azlactone synthesis. Twenty-one compounds were selected and screened at the National Cancer Institute (NCI), USA, for anticancer activity at a single high dose (10-5M) in full NCI 60 cell panel assay. Results and Conclusion: The selected compounds (13a, 13b, 13c, 13f, 13h, 13i, 13j, 18h, 18i, 21a4) were found to be active against different cancer cell lines. The compound, 5-((5-chloro-3-methyl-1- phenyl-1H-pyrazol-4-yl)methylene)-2-(4-nitrobenzoyl)-3-phenyl-1,2-dihydro-1,2,4-triazin-6(5H)-one (13a) was found to be a potent anti-cancer agent as electron-rich moiety on phenyl at position 2 of triazine nucleus, having a great impact on anticancer activity.

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Yamanaka, Hiroshi, Shoetsu Konno, Setsuya Ohba, Mitsuko Agata, Yuichi Aizawa, and Mataichi Sagi. "Studies on as-Triazine Derivatives. VIII. Synthesis of 5-Substituted 1,2,4-Triazines." HETEROCYCLES 26, no. 12 (1987): 3259. http://dx.doi.org/10.3987/r-1987-12-3259.

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29

Krutz, L. Jason, Robert M. Zablotowicz, and Krishna N. Reddy. "Selection Pressure, Cropping System, and Rhizosphere Proximity Affect Atrazine Degrader Populations and Activity ins-Triazine–Adapted Soil." Weed Science 60, no. 3 (2012): 516–24. http://dx.doi.org/10.1614/ws-d-11-00104.1.

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A field study was conducted on ans-triazine–adapted soil to determine the effects ofs-triazine exclusion interval (1, 2, 3, or 4 yr), crop production system (continuous corn or continuous soybean), and rhizosphere proximity (bulk or rhizosphere soil) on atrazine degrader populations and activity. Atrazine degrader populations were quantified by a radiological Most Probable Number technique, while degrader activity was assessed via mineralization of ring-labeled14C-atrazine. As thes-triazine exclusion interval increased, atrazine degrader populations declined exponentially, regardless of crop or rhizosphere proximity. Crop and exclusion interval interacted to affect degrader populations (P = 0.0043). Pooled over rhizosphere and bulk soil, degrader populations were 1.5-fold higher and declined 2.8-fold faster in soybean than corn. An interaction between rhizosphere proximity and exclusion interval was also noted (P = 0.0021), whereby degrader populations were 1.9-fold higher and declined 2.8-fold slower in rhizosphere compared with bulk soil, regardless of crop. The time required for 50% mineralization of ring-labeled14C-atrazine (DT50) following exclusion ofs-triazine herbicides increased linearly at a rate of 2.2 d yr−1. In contrast, the DT50for this site prior to a knowns-triazine application was 85 d and declined exponentially over 5 yr of successive atrazine applications: 24.5 d after 1 yr, 10.8 d after two successive years, and 3.8 d after five successive atrazine applications. Omittings-triazines can reduce degrader populations and activity in adapted soils, but more than 4 yr is required to return mineralization kinetics to nonadapted levels, regardless of crop or rhizosphere proximity.

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30

ME Shelke. "Synthesis and evaluation of newly1-substituted-(2H)-2-thio-4-(3-substitutedthiocarbamido-1-yl)-6-(2-imino-4-thio-5- substitutedbiureto-1-yl) 1, 2-dihydro-S-triazines as potent antimicrobial agents." GSC Biological and Pharmaceutical Sciences 13, no. 3 (2020): 109–12. http://dx.doi.org/10.30574/gscbps.2020.13.3.0245.

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The search for novel antibiotics is of immense importance in research areas around the world for agricultural, pharmaceutical, and industrial applications. The s-triazines are widely used as an important biological tool for the production of a wide range of novel secondary metabolites. In the present study, the series of 1-substituted-(2H)-2-thio-4-(3- substitutedthiocarbamido-1-yl)-6-(2-imino-4-thio- 5- substitutedbiureto-1-yl) 1,2-dihydro-s-triazine [4a(i) to 4f(iii)] have been obtained by the isomerisation of 2-(2-imino-4-thio-5- substitutedbiureto-1-yl)-4-(3- substitutedthio-carbamido-1-yl)-6- substitutedimino-1,3,5-thiadiazine [3a(i) to 3f(iii)] in presence of ethanolic sodium bicarbonate solution. The later were synthesized by the chemical action of 1, 3-bis-(N-phenylamidinothiocarbamido)-thiocarbamide and aryl/alkylisocyanodichlorides. On the basis of IR, PMR spectrum data and elemental analysis, the structures of all these compounds were established. The synthesized s-triazine were analyzed for antimicrobial activities by cup plate diffusion method and exhibited a broad spectrum of antimicrobial activity against test pathogens. The isolate was tested for the ability to grow in the presence of antibiotic, such as ciprofloxacin at the same concentration. Thus, the study concludes with the eco-friendly route for synthesizing s-triazine with antibacterial activity against clinically important pathogens.

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31

ME, Shelke. "Synthesis and evaluation of newly1-substituted-(2H)-2-thio-4-(3-substitutedthiocarbamido-1-yl)-6-(2-imino-4-thio-5- substitutedbiureto-1-yl) 1, 2-dihydro-S-triazines as potent antimicrobial agents." GSC Biological and Pharmaceutical Sciences 13, no. 3 (2020): 109–12. https://doi.org/10.5281/zenodo.4415130.

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The search for novel antibiotics is of immense importance in research areas around the world for agricultural, pharmaceutical, and industrial applications. The s-triazines are widely used as an important biological tool for the production of a wide range of novel secondary metabolites. In the present study, the series of 1-substituted-(2H)-2-thio-4-(3- substitutedthiocarbamido-1-yl)-6-(2-imino-4-thio- 5- substitutedbiureto-1-yl) 1,2-dihydro-s-triazine [4a(i) to 4f(iii)]  have been obtained by the isomerisation of 2-(2-imino-4-thio-5- substitutedbiureto-1-yl)-4-(3- substitutedthio-carbamido-1-yl)-6- substitutedimino-1,3,5-thiadiazine [3a(i) to 3f(iii)] in presence of ethanolic sodium bicarbonate solution. The later were synthesized by the chemical action of 1, 3-bis-(N-phenylamidinothiocarbamido)-thiocarbamide and aryl/alkylisocyanodichlorides. On the basis of IR, PMR spectrum data and elemental analysis, the structures of all these compounds were established. The synthesized s-triazine were analyzed for antimicrobial activities by cup plate diffusion method and exhibited a broad spectrum of antimicrobial activity against test pathogens. The isolate was tested for the ability to grow in the presence of antibiotic, such as ciprofloxacin at the same concentration. Thus, the study concludes with the eco-friendly route for synthesizing s-triazine with antibacterial activity against clinically important pathogens.

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32

Hamri, Salha, Abderrafia Hafid, Mostafa Khouili, Lahcen El Ammari, and El Mostafa Ketatni. "3-Methylsulfanyl-5-phenyl-1,2,4-triazine." Acta Crystallographica Section E Structure Reports Online 70, no. 6 (2014): o720. http://dx.doi.org/10.1107/s1600536814011830.

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In the molecule of the title compound, C10H9N3S, the dihedral angle between the triazine and phenyl rings is 11.77 (7)°. In the crystal, molecules are linked by π–π stacking interactions [centroid–centroid distances = 3.7359 (3) and 3.7944 (4) Å], forming layers parallel to thebcplane.

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33

Makarenkov, Anton V., Sergey S. Kiselev, Elena G. Kononova, et al. "Synthesis, Characterization and DFT Study of a New Family of High-Energy Compounds Based on s-Triazine, Carborane and Tetrazoles." Molecules 27, no. 21 (2022): 7484. http://dx.doi.org/10.3390/molecules27217484.

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An efficient one-pot synthesis of carborane-containing high-energy compounds was developed via the exploration of carbon–halogen bond functionalization strategies in commercially available 2,4,6-trichloro-1,3,5-triazine. The synthetic pathway first included the substitution of two chlorine atoms in s-triazine with 5-R-tetrazoles (R = H, Me, Et) units to form disubstituted tetrazolyl 1,3,5-triazines followed by the sequential substitution of the remaining chlorine atom in 1,3,5-triazine with carborane N- or S-nucleophiles. All new compounds were characterized by IR- and NMR spectroscopy. The structure of four new compounds was confirmed by single crystal X-ray diffraction analysis. The density functional theory method (DFT B3LYP/6-311 + G*) was used to study the geometrical structures, enthalpies of formation (EOFs), energetic properties and highest occupied and lowest unoccupied molecular orbital (HOMO and LUMO) energies and the detonation properties of synthesized compounds. The DFT calculation revealed compounds processing the maximum value of the detonation velocity or the maximum value of the detonation pressure. Theoretical terahertz frequencies for potential high-energy density materials (HEDMs) were computed, which allow the opportunity for the remote detection of these compounds.

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34

Ohsumi, Tadashi, and Hans Neunhoeffer. "Synthesis of 1,2,4-triazines - XIV. Regioselective synthesis of ethyl 1,2,4-triazine-5-carboxylates." Tetrahedron 48, no. 25 (1992): 5227–34. http://dx.doi.org/10.1016/s0040-4020(01)89020-7.

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35

Baldaniya, B. B., and P. K. Patel. "Synthesis, Antibacterial and Antifungal Activities ofsDerivatives." E-Journal of Chemistry 6, no. 3 (2009): 673–80. http://dx.doi.org/10.1155/2009/196309.

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SeveralNʹ-{4-[(3-chloro-4-fluorophenyl) amino]-6-[(-aryl) amino] -1, 3, 5-triazin-2-yl} isonicotinohydrazides (6a-r) andN2-(Aryl)-N4,N6-dipyrimidin-2-yl-1,3,5-triazine-2,4,6-triamines (4a-o) were prepared. All newly synthesized compounds have been tested for their antibacterial activity against gram (+)ve and gram (-)ve bacteria and also on different strains of fungi. Introduction of -OH, -OCH3, -NO2, -Cl and -Br groups to the heterocyclic frame work enhanced antibacterial and antifungal activities.

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36

Zálešák, František, Jan Slouka, and Jakub Stýskala. "General Synthesis of 1-Aryl-6-azaisocytosines and Their Utilization for the Preparation of Related Condensed 1,2,4-Triazines." Molecules 24, no. 19 (2019): 3558. http://dx.doi.org/10.3390/molecules24193558.

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A simple general synthesis of 1-aryl-6-azaisocytosine-5-carbonitriles 4 is described. This method is based on coupling diazonium salts with cyanoacetylcyanamide 2 and then cyclization of the formed 2-arylhydrazono-2-cyanoacetylcyanamides 3. The 6-azaisocytosines 4 were studied with respect to tautomeric equilibrium and the transformation of functional groups, and used in the synthesis of the condensed heterocyclic compounds: Purine isosteric imidazo[2,1-c]-[1,2,4]triazine 8 and the 1,2,4-triazino[2,3-a]quinazolines 9–12.

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37

Novodvorskyi, Yevhenii, Dmitry Lega, Igor Komarov, Iryna Zhuravel, Oleg Moskalenko, and Anatolii Demchenko. "Synthesis and antioxidant activity of 3-(2-R-ylidenehydrazinyl)-6-tert-butyl-4H-[1,2,4]triazin-5-ones." Pharmacia 69, no. 3 (2022): 719–31. http://dx.doi.org/10.3897/pharmacia.69.e86036.

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Synthesis and structure elucidation of several series of new hydrazones containing 1,2,4-triazine-5-one core and their antioxidant activity are presented. The target compounds have been synthesized via interaction of either 4-amino-6-(tert-butyl)-3-hydrazinyl-1,2,4-triazin-5(4H)-one or 6-(tert-butyl)-3-hydrazinyl-1,2,4-triazin-5(2H)-one with a wide range of compounds with a carbonyl group in moderate to high yields. Molecular structures of the synthesized compounds were conﬁrmed by 1H NMR, 13C NMR, and elemental analyses. The antioxidant activity of these compounds against ascorbic acid was screened to determine their potential as promising oxidative stress suppressors. Our data showed that hydrazones derived from 4-amino-6-(tert-butyl)-3-hydrazinyl-1,2,4-triazin-5(4H)-one are the most active antioxidants among all tested compounds. Furthermore, 3 compounds of this series have been proved to be twice as active as ascorbic acid does. The conclusions are substantiated for in-depth investigations of these derivatives as promising agents for the treatment of disorders accompanied by oxidative stress.

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38

Novodvorskyi, Yevhenii, Dmitry Lega, Igor Komarov, Iryna Zhuravel, Oleg Moskalenko, and Anatolii Demchenko. "Synthesis and antioxidant activity of 3-(2-R-ylidenehydrazinyl)-6-tert-butyl-4H-[1,2,4]triazin-5-ones." Pharmacia 69, no. (3) (2022): 719–31. https://doi.org/10.3897/pharmacia.69.e86036.

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Synthesis and structure elucidation of several series of new hydrazones containing 1,2,4-triazine-5-one core and their antioxidant activity are presented. The target compounds have been synthesized via interaction of either 4-amino-6-(tert-butyl)-3-hydrazinyl-1,2,4-triazin-5(4H)-one or 6-(tert-butyl)-3-hydrazinyl-1,2,4-triazin-5(2H)-one with a wide range of compounds with a carbonyl group in moderate to high yields. Molecular structures of the synthesized compounds were confirmed by <sup>1</sup>H NMR, <sup>13</sup>C NMR, and elemental analyses. The antioxidant activity of these compounds against ascorbic acid was screened to determine their potential as promising oxidative stress suppressors. Our data showed that hydrazones derived from 4-amino-6-(tert-butyl)-3-hydrazinyl-1,2,4-triazin-5(4H)-one are the most active antioxidants among all tested compounds. Furthermore, 3 compounds of this series have been proved to be twice as active as ascorbic acid does. The conclusions are substantiated for in-depth investigations of these derivatives as promising agents for the treatment of disorders accompanied by oxidative stress.

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39

Velihina, Y. S., S. G. Pilyo, I. V. Ivanova, and V. S. Brovarets. "Synthesis of pyrazolo[1,5-a][1,3,5]triazine and oxazolo[4,5-d]pyrimidine derivatives and study of their vasodilator activity." Voprosy Khimii i Khimicheskoi Tekhnologii, no. 2 (May 2023): 51–60. http://dx.doi.org/10.32434/0321-4095-2023-147-2-51-60.

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A number of pyrazolo[1,5-a][1,3,5]triazine and oxazolo[4,5-d]pyrimidine derivatives were synthesized and characterized. Pyrazolo[1,5-a][1,3,5]triazines with various substituents in the fourth position and a dichloromethyl group in the second position were obtained by the heterocyclization reaction of available N-(2,2-dichloro-1-cyanoethenyl)carboxamides and 5-aminopyrazoles. Oxazolo[4,5-d]pyrimidines were obtained by treating 2-phenyl-4-dichloromethylene-1,3-oxazol-5(4H)-one with the corresponding arylamidine hydrochloride in the presence of triethylamine. The resulting 4,5-dihydro-1H-imidazol-5(4)-ones undergo recyclization with subsequent cyclocondensation to the corresponding oxazolo[4,5-d]pyrimidin-7-ones when heated in pyridine. Oxazolo[4,5-d]pyrimidines with a labile chlorine atom in position 7, whose substitution with various amines leads to 7-aminoderivatives of oxazolo[4,5-d]pyrimidine, were obtained by heating the latter in phosphorus (V) oxychloride in the presence of N,N-dimethylaniline. The study of the effect of the synthesized compounds on vascular tone showed that some of the studied samples exhibited vasodilator activity of varying strength. It was established that 2-dichloromethyl-7-methyl-4-(furan-2-yl)pyrazolo[1,5-a][1,3,5]triazine and 2-dichloromethyl-7-methyl-4-(pyridin-3-yl)pyrazolo[1,5-a][1,3,5]triazine showed a pronounced dose-dependent vasodilator effect and therefore, subject to their further research, may be promising for the development of new vasodilator drugs. The study of the biological activity of oxazolo[4,5-d]pyrimidine derivatives did not reveal potential vasodilator agents among the presented compounds, as they demonstrated a low vasodilator effect or did not show vasoactivity.

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40

Wolińska, Ewa, Zbigniew Karczmarzyk, Andrzej Rykowski, Zofia Urbańczyk-Lipkowska, and Przemysław Kalicki. "2-(3-Chloro-5,6-diphenyl-2,5-dihydro-1,2,4-triazin-5-yl)-2-methylpropanenitrile." Acta Crystallographica Section E Structure Reports Online 68, no. 6 (2012): o1938. http://dx.doi.org/10.1107/s1600536812023252.

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The title compound, C19H17ClN4, was obtained from the reaction of 3-chloro-5,6-diphenyl-1,2,4-triazine with isobutyronitrile in the presence of lithium diisopropylamide as an unexpected product of covalent addition of isobutyronitrile carbanion to the C-5 atom of the 1,2,4-triazine ring. The 2,5-dihydro-1,2,4-triazine ring is essentially planar (r.m.s. deviation = 0.0059 Å) and the 5- and 6-phenyl substituents are inclined to its mean plane with dihedral angles of 89.97 (4) and 55.52 (5)°, respectively. Intramolecular C—H...N interactions occur. In the crystal, molecules related by a c-glide plane are linked into zigzag chains along [001] by N—H...N hydrogen bonds.

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41

Branowska, Danuta, Stanislaw Ostrowski, and Andrzej Rykowski. "3-Phenyl-5-[1-(phenylsulphonyl)-pent-4-yn]-1,2,4-triazine and 3-Phenyl-5-[1-(phenylsulphonyl)-hex-5-yn]-1,2,4-triazine." Molbank 2003, no. 2 (2003): M314. http://dx.doi.org/10.3390/m314.

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42

Neunhoeffer, Hans, Diethard Reichel, Birgit Cullmann, and Ingrid Rehn. "Zur Chemie der 1,2,4-Triazine, XIV. Synthese und Reaktionen von 5-Chlor-1,2,4-triazinen." Liebigs Annalen der Chemie 1990, no. 7 (1990): 631–40. http://dx.doi.org/10.1002/jlac.1990199001121.

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43

Lazrek, Bihi H., and Raymond P. Panzica. "As-Triazine-3, 5-Dione Acyclic Nucleosides." Nucleosides and Nucleotides 4, no. 1-2 (1985): 279. http://dx.doi.org/10.1080/07328318508077888.

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44

Rybakova, A., D. Kim, V. Sharutin, and P. Slepukhin. "Synthesis and electrophilic heterocyclization of 3-alkenylsulfanyl-5-phenyl-1,2,4-triazines under the action of iodine and bromine." Bulletin of the South Ural State University series "Chemistry" 15, no. 1 (2023): 93–104. http://dx.doi.org/10.14529/chem230110.

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Derivatives of 1,2,4-triazine-3-thione are interesting research objects due to a wide range of their applications: drugs, optical substances, precursors for synthesis of new pyridine systems by the Diels-Alder reaction. In the present study, using alkylation of 5-phenyl-2,3-dihydro-1,2,4-triazine-3-thione (1) by 3-chloro-2-methyl-propene, 2,3-dibromopropene-1, 1-bromo-3-methylbut-2-ene and 4-brombut-1-ene, we have obtained 3-(2-methylprop-1-enyl)-, 3-(2-bromoprop-1-enyl)-, 3-prenylsulfanyl- and 3-butenylsulfanyl-5-phenyl-1,2,4-triazines (2a-d), previously unknown. In the 1H NMR spectrum of compound 2b, the shifts of the signal of pro-tons of the SCH2 group and the signal of protons of the vinyl group into a weak field by 0.48 ppm and 0.60 ppm can be observed, compared to the similar signals in the spectrum of 3-allylsulfanyl-5-phenyl-1,2,4-triazine. This may be due to the bromine atom in the allyl fragment. The weakest-field signal in the 13C NMR spectra of compounds 2a-d in the region of 171.86–173.68 ppm refers to the aromatic carbon atom of the triazine cycle in the third position (C-3), bound to a sulfur atom and two nitrogen atoms. New condensed heterocyclic systems of ionic type with a bridging nitrogen atom have been synthesized by electrophilic heterocyclization of methallyl-, bromallyl-, prenyl- and butenyl sulfides 2a-d. At the same time, [1,3]thiazolo[3,2-b][1,2,4]triazinium halides have been obtained by heterocyclization of compounds 2a,2b, and [1,3]thiazino[3,2–b][1,2,4]triazinium halides have been produced by heterocyclization of com-pounds 2c,2d. In the 1H NMR spectra of triazinium halides, a characteristic shift of the signal of the H-6 aromatic proton to the weak field region is observed in comparison with the similar sig-nal in the spectrum of the initial 2a-d sulfides. In the 13C NMR spectra of triazinium halides, there is a shift in the signal of the aromatic carbon atom associated with a sulfur atom and two nitrogen atoms (in the region of 162.56-172.42 ppm), which can be explained by the appearance of a positively charged nitrogen atom in their structure.

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Ionescu, M., I. Mihalache, V. Zugravu, and S. Mihai. "Inherently Flame Retardant Rigid Polyurethane Foams Based on New Triazinic Polyether Polyols." Cellular Polymers 13, no. 1 (1994): 57–68. http://dx.doi.org/10.1177/026248939401300104.

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The synthesis of new triazinic polyols by oxyalkylation with the propyleneoxide of some well known condensation products derived from melamine (2,4,6-triamino-1,3,5-triazine), a heteroaromatic chain initiator, has been studied. By using the synthesized aromatic triazinic polyols in conventional foaming processes, rigid polyurethane foams with excellent physico-mechanical properties and inherent flame retardancy are obtained, better than those of rigid polyurethane foams derived from conventional aliphatic polyols based on sucrose. A new additive flame retardant with a similar heteroaromatic triazinic structure (1, 3, 5-trichlormethylisocyanurate) was also successfully evaluated. The non expensive and accessible raw materials, the facility of the reactions involved in this kind of synthesis, make the studied method very attractive from technological points of view.

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Chen, Chih-Wei, Tzu-Ling Yang, and Yu-Chie Chen. "Using Magnetic Micelles Combined with Carbon Fiber Ionization Mass Spectrometry for the Screening of Trace Triazine Herbicides from Aqueous Samples." Molecules 29, no. 1 (2023): 137. http://dx.doi.org/10.3390/molecules29010137.

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Triazine herbicides are commonly used in agriculture to eliminate weeds. However, they can persist in the environment. In this study, we explored a new method for detecting triazine herbicides in aqueous samples. We selected two triazine herbicides, namely, prometryn and ametryn, as model herbicides. To generate magnetic probes, we mixed aqueous Gd3+ with aqueous sodium dodecyl sulfate (SDS), which created magnetic probes made of Gd3+-SDS micelles. These probes showed a trapping capacity for the model herbicides. Results indicated that the trapping capacities of our magnetic probes for ametryn and prometryn were approximately 466 and 468 nmol mg−1, respectively. The dissociation constants of our probes toward ametryn and prometryn were 2.92 × 10−5 and 1.27 × 10−5, respectively. This is the first report that the developed magnetic probes can be used to trap triazine herbicides. For detection, we used carbon fiber ionization mass spectrometry (CFI-MS), which can be used to directly detect semi-volatiles from the samples in the condensed phase. Because of the semi-volatility of triazine herbicides, the herbicides trapped by the magnetic probes can be directly analyzed by CFI-MS without any elution steps. In addition, we also demonstrated the feasibility of using our approach for detecting triazine herbicides in lake water and drinking water.

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47

Alharbi, Abdulrahman Salim, and Nawaa Ali Alshammari. "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." Mediterranean Journal of Chemistry 8, no. 6 (2019): 486–93. http://dx.doi.org/10.13171/mjc861907296asa.

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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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Abdou, W. M., M. M. Sidky, and H. Wamhoff. "Photochemistry of Pesticides, 10 [1] Photodegradation of O,O-Diethyl-S(3,4-dihydro-4-oxobenzo[d][1,2,3]triazin- 3-yl-methyl)phosphorodithioate (Azinphos-ethyl)." Zeitschrift für Naturforschung B 42, no. 7 (1987): 907–10. http://dx.doi.org/10.1515/znb-1987-0720.

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Abstract The photodegradation of Azinphos-ethyl (1) in chloroform and methanol solution has been studied. 3,4-Dihydro-3-methyl-4-oxobenzo[d][1,2,3]triazine (3), 3,4-dihydro-4-oxo-benzo[d]- [1,2,3]triazine (5), O,O-diethyl-O(3-methylbenzo[d][1,2,3]triazine-4-yl)p hosph ate (8), N-methylanthranilic acid (11) (in methanol: methyl ester 12), and sulfur have been isolated and characterized as photoproducts. The decay mechanism is discussed.

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Cai, Dong, Tai Li, Qian Xie, et al. "Synthesis, Characterization, and Biological Evaluation of Novel 7-Oxo-7H-thiazolo[3,2-b]-1,2,4-triazine-2-carboxylic Acid Derivatives." Molecules 25, no. 6 (2020): 1307. http://dx.doi.org/10.3390/molecules25061307.

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A series of novel 7-oxo-7H-thiazolo[3,2-b]-1,2,4-triazine-2-carboxylic acid derivatives was synthesized in good yields by a multi-step procedure that included the generation of the S-alkylated derivatives from 6-substituted arylmethyl-3-mercapto-1,2,4-triazin-5-ones with ethyl 2-chloroacetoacetate, intramolecular cyclization with microwave irradiation, hydrolysis and amidation. All of the target compounds were fully characterized through 1H-NMR, 13C-NMR and HRMS spectra. The intramolecular cyclization occurred regioselectively at the N2-position of 1,2,4-triazine ring, which was confirmed by compound 3e using single-crystal X-ray diffraction analysis. The antibacterial and antitubercular activities of the target compounds were evaluated. Compared with Ciprofloxacin and Rifampicin, compounds 5d, 5f and 5g containing the terminal amide fragment exhibited broad spectrum antibacterial activity, and carboxylic acid derivatives or its corresponding ethyl esters had less effect on antibacterial properties. The most potent compound 5f also displayed excellent in vitro antitubercular activity against Mycobacterium smegmatis (minimum inhibitory concentration (MIC) = 50 μg/mL) and better growth inhibition activity of leucyl-tRNA synthetase (78.24 ± 4.05% at 15 μg/mL).

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Chrzan, Julia, Anna Karolina Drabczyk, Izabela Siemińska, et al. "Green and Efficient Synthetic Protocol for 1,3,5-Triazine Derivatives with Anticancer Potential Against Colorectal Cancer." Molecules 30, no. 11 (2025): 2437. https://doi.org/10.3390/molecules30112437.

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Colorectal cancer (CRC) remains a major global health challenge, necessitating the development of more effective and environmentally sustainable treatments. This study presents a novel green synthetic protocol for 1,3,5-triazine derivatives with anticancer potential, employing both microwave-assisted and ultrasound-assisted methods. The synthesis was optimized using 4-chloro-N-(2-chlorophenyl)-6-(morpholin-4-yl)-1,3,5-triazin-2-amine as the key intermediate, with sodium carbonate, TBAB, and DMF providing optimal yields under microwave conditions. To enhance sustainability, a modified sonochemical method was also developed, enabling efficient synthesis in aqueous media with a minimal use of organic solvents. A series of nine morpholine-functionalized derivatives were synthesized and evaluated for cytotoxic activity against SW480 and SW620 colorectal cancer cell lines. Compound 11 demonstrated superior antiproliferative activity (IC₅₀ = 5.85 µM) compared to the reference drug 5-fluorouracil, while compound 5 showed promising dual-line activity. In silico ADME analysis supported the drug likeness of the synthesized compounds, and biomimetic chromatography analysis confirmed favorable physicochemical properties, including lipophilicity and membrane affinity. These results underscore the potential of the developed protocol to produce bioactive triazine derivatives through an efficient, scalable, and environmentally friendly process, offering a valuable strategy for future anticancer drug development.

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Journal articles on the topic '5-triazine'

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