- Synthesis and characterization of lanthanide complexes with a pentadentate triazine-based ligand
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A series of mononuclear [Ln(L)(H2O)(NO3)(solv)]·solv, (Ln?=?Pr (1), Nd (2), Sm (3), Eu (4), Gd (5), Tb (6–6a), Dy (7); solv?=?DMF, DMSO, H2O) and L?=?2,4-bis(2-hydroxybenzylidenehydrazino)-6-methoxy-s-triazine complexes were prepared. The lanthanide(III) ions are nine-coordinated in the complexes and are bound to the O atoms of bidentate nitrate, three N and two O atoms of a pentadentate L ligand and one O atom from water and one O atom from dimethylformamide with a spherical capped square antiprism coordination environment in 1–7. The compounds have been characterized by means of elemental analysis, IR spectroscopy, UV–Vis spectroscopy, X-ray diffraction, and thermal analysis. Lanthanide-centered emission of the complexes is overlapped by the ligand emission.
- Pavelek, Lubomír,Ladányi, Vít,Ne?as, Marek,Moravec, Zdeněk,Wichterle, Kamil
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- Synthesis and antiproliferating activity of iron chelators of hydroxyamino-1,3,5-triazine family
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We synthesized and evaluated new specific tridentate iron(III) chelators of 2,6-bis[hydroxyamino]-1,3,5-triazine (BHT) family for use in iron deprivation cancer therapy. Physical properties of BHT chelators are easily customizable allowing easy penetration through cellular membranes. Antiproliferative activity of new BHT chelators was studied on MDA-MB-231 and MiaPaCa cells and compared to a clinically available new oral iron chelator, deferasirox (DFX). The antiproliferative activity of new chelators was found to correlate with iron(III) chelation ability and some of analogs showed substantially higher antiproliferative activity than DFX.
- Sun, Daekyu,Melman, Galina,LeTourneau, Nickolas J.,Hays, Allison M.,Melman, Artem
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- Inhibition of acetolactate synthase isozyme II from Escherichia coli by a new azido-photoaffinity sulfonylurea
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The sulfonylurea herbicides are very patent inhibitors of acetolactate synthase (ALS). These compounds have been reported as 'extraneous inhibitors' due to the fact that their inhibition site corresponds to neither the catalytic site nor the regulatory sites of the enzyme. So far, the complexity of the ALS reaction and the reversible binding mode of sulfonylureas have hampered any attempt to locate the inhibitor domain. Toward this goal, a photoactivatable azidosulfonylurea has been synthesized. The azido derivative was analyzed for its photochemical and in vitro biological properties toward the bacterial ALS isozyme II. Similar to other ALS inhibitors, azidosulfonylurea potently inhibited ALS II with estimated initial and final dissociation K(i) constant values of 52 and 300 nM, respectively, and slowly inactivated the enzyme. After inhibition, removal of the free azido inhibitor and precipitation with ammonium sulfate of the azidosulfonylurea/ALS II complex led to complete though slow recovery of the enzyme activity. Following photoreaction of the inhibited complex and removal of the free inhibitor under the same conditions, the bacterial enzyme conversely exhibited stable inactivation. These results suggest that the newly synthesized azidosulfonylurea is capable of undergoing covalent reaction with ALS II, and hence it might be useful, once radiolabeled, to shed light on the inhibitor binding site of ALS.
- Ortega, Florence,Bastide, Jean
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- Triazine based Mn (II) and Mn (II)/Ln (III) complexes: Synthesis, characterization and catecholase activities
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In the current work, two triazine-based multidentate ligands (H2L1 and H2L2) and their homo-dinuclear Mn (II), mononuclear Ln (III) and hetero-dinuclear Mn (II)/Ln (III) (Where Ln: Eu or La) complexes were synthesized and characterized by spectroscopic and analytical methods. Single crystals of a homo-dinuclear Mn (II) complex {[Mn (HL1)(CH3OH)](ClO4·CH3OH}2 (1) were obtained and the molecular structure was determined by X-ray diffraction method. In the structure of the complex, each Mn (II) ion is seven-coordinate and one of the phenolic oxygen bridges two Mn (II) centre forming a dimeric structure. The UV–Vis. and photoluminescence properties of synthesized ligands and their metal complexes were investigated in DMF solution and the compounds showed emission bands in the UV–Vis. region. The catecholase enzyme-like activity of the complexes were studied for 3,5-DTBC → 3,5-DTBQ conversion in the presence of air oxygen. Homo-dinuclear Mn (II) complexes (1 and 4) were found to efficiently catalyse 3,5-DTBC → 3,5-DTBQ conversion with the turnover numbers of 37.25 and 35.78?h?1 (kcat), respectively. Mononuclear Eu (III) and La (III) complexes did not show catecholase activity.
- Celik, Derya,Kose, Muhammet
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- A highly emissive fluorescent Zn-MOF: molecular decoding strategies for solvents and trace detection of dunnite in water
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The strategic exploration of a highly emissive methoxy and amine-functionalized fluorescent three-dimensional MOF, {[Zn2(MTAIA)(DMF)2(H2O)]·H2O}n (1), based on a new custom-designed tetracarboxylate (H4MTAIA) ligand, is demonstrated for (i) decoding of solvents based on solvent polarity parameters and an unprecedented dual readout (lifetime and quantum yield) identification scheme and (ii) ultrafast detection of highly explosive dunnite, which was used during World War I, with high selectivity in water at the ppb level for the first time. This is a rare example of such a dual functional chemosensor.
- Das, Prasenjit,Mandal, Sanjay K.
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- Two heptacoordinated manganese(II) complexes of giant pentadentate s-triazine bis-Schiff base ligand: Synthesis, crystal structure, biological and DFT studies
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A new s-triazine bis-Schiff base chelating ligand (L) and two of its heptacoordinated Mn(II) complexes were synthesized and characterized. Reaction of solid Mn(NO3)2·4H2O with methanolic solution of the ligand (L; 5) afford [MnL(MeOH)NO3]NO3.MeOH; (6). While, repeating the reaction in water/methanol solution, the complex [MnL(H2O)2](NO3)2; (7) was formed. In both complexes, the Mn(II) is coordinated with L as a pentadentate ligand via its N-atoms augmented with two axial Mn–O bonds leading to a distorted pentagonal bipyramidal configuration around the Mn(II) ion. The two-pyridine moieties at the end of the ligand arms are twisted from one another due to the short contact distance between the two hydrogen atoms at the 6 position of the pyridine moieties. As a result, the strength of the Mn–N bonds decrease ongoing from the triazine moiety towards the outside of the ligand arms. The atoms in molecules topological parameters correlated well with the Mn–N distances. The Mn–N and Mn–O bonds were analyzed using natural bond orbital calculations. Both complexes showed higher thermal stability than the free ligand. Antimicrobial studies showed that 7 and L are the best candidates as antifungal and antibacterial agents, respectively. The mechanism of biological activity depends on the interactions between the compound and cell wall.
- Soliman, Saied M.,El-Faham, Ayman,Elsilk, Sobhy E.,Farooq, Muhammad
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- Synthesis of Amidation Agents and Their Reactivity in Condensation Reactions
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Nowadays, the development of new approaches which smartly bypass the use of harsh reaction conditions and hazardous chemicals covers a pivotal role. In this research paper the synthesis, characterization, and application of novel libraries of triazine bis-quaternary ammonium salts, employed as coupling agents to produce amides is reported. Full characterization of the novel compounds by 1H and 13C NMR, FT-IR spectroscopy, ESI-HRMS, and elemental analysis is provided. Furthermore, a comparison in terms of activity of the preformed triazine compounds versus in situ formulations has been evaluated for the formation of amides in the presence of phenylethylamine and different aliphatic or aromatic acids. A possible correlation between the chemical structure of the triazine and their reactivity for the formation of the triazine bis-quaternary ammonium salts is also reported. Moreover, best performing condensation agents have been further tested for the cross-linking of collagen powder as possible wet white tanning systems, for sustainable and environmentally friendly leather tanning.
- Sole, Roberto,Agostinis, Lodovico,Conca, Silvia,Gatto, Vanessa,Bardella, Noemi,Morandini, Andrea,Buranello, Chiara,Beghetto, Valentina
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supporting information
p. 1672 - 1682
(2021/02/01)
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- Synthesis and Antimicrobial Evaluation of Bis-morpholine Triazine Quaternary Ammonium Salts
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Efficient, environmentally and economically sustainable, and nontoxic antibacterial products are of global relevance in the fight against microorganism contamination. In this work, an easy and straightforward method for the synthesis of bis-morpholino triazine quaternary ammonium salts (bis-mTQAS) is reported, starting from 2,4,6-trichloro-1,3,5-triazine or 2,4-dichloro-6-methoxy-1,3,5-triazine and various N-alkylmorpholines. Bis-mTQAS were tested as antimicrobials against Gram-negative and Gram-positive bacterial strains. The best-performing bis-mTQAS were found to achieve total disinfection against Staphylococcus aureus ATCC 25923 and Escherichia coli ATCC 25922 at 50 and 400 μg/mL, respectively. Distinctively, bis-mTQAS with the highest antimicrobial efficiency had lowest cytotoxicity.
- Morandini, Andrea,Leonetti, Benedetta,Riello, Pietro,Sole, Roberto,Gatto, Vanessa,Caligiuri, Isabella,Rizzolio, Flavio,Beghetto, Valentina
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supporting information
p. 3172 - 3176
(2021/08/03)
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- Interfering with the Tumor-Immune Interface: Making Way for Triazine-Based Small Molecules as Novel PD-L1 Inhibitors
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The inhibition of the PD-1/PD-L1 axis by monoclonal antibodies has achieved remarkable success in treating a growing number of cancers. However, a novel class of small organic molecules, with BMS-202 (1) as the lead, is emerging as direct PD-L1 inhibitors. Herein, we report a series of 2,4,6-tri- and 2,4-disubstituted 1,3,5-triazines, which were synthesized and assayed for their PD-L1 binding by NMR and homogeneous time-resolved fluorescence. Among them, compound 10 demonstrated to strongly bind with the PD-L1 protein and challenged it in a co-culture of PD-L1 expressing cancer cells (PC9 and HCC827 cells) and peripheral blood mononuclear cells enhanced antitumor immune activity of the latter. Compound 10 significantly increased interferon γrelease and apoptotic induction of cancer cells, with low cytotoxicity in healthy cells when compared to 1, thus paving the way for subsequent preclinical optimization and medical applications.
- Russomanno, Pasquale,Assoni, Giulia,Amato, Jussara,D'Amore, Vincenzo Maria,Scaglia, Riccardo,Brancaccio, Diego,Pedrini, Martina,Polcaro, Giovanna,La Pietra, Valeria,Orlando, Paolo,Falzoni, Marianna,Cerofolini, Linda,Giuntini, Stefano,Fragai, Marco,Pagano, Bruno,Donati, Greta,Novellino, Ettore,Quintavalle, Cristina,Condorelli, Gerolama,Sabbatino, Francesco,Seneci, Pierfausto,Arosio, Daniela,Pepe, Stefano,Marinelli, Luciana
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p. 16020 - 16045
(2021/11/10)
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- Synthesis and kinetic study of a series of chloro- and m-carboxypyridium triazinyl reactive dyes
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Five monochloro-s-triazinyl reactive dyes (MCT) and five m-carboxypyridium-s-triazinyl reactive dyes (NTR) were synthesised with the same red chromophore bearing an –NHCN, –OCH3, –CH3NSO2CH3, –N-methyl phenyl or –OH group as ‘second-leg’ substituents. A kinetic study of the hydrolysis of these dyes was conducted, and the rate constant (kobs) and half-life time values were determined. The kobs of the MCT and NTR dyes was found to follow the order –OCH3 > –CH3NSO2CH3 > –N-methyl phenyl > –NHCN > –OH, which was approximately in agreement with the values obtained for the Hammett substituent constants. Overall, the higher the electron-donating property of the substituent on meta-position to the leaving group in the triazine ring, the lower the hydrolysis rate constant.
- Huang, Huei-Chin,Wu, Chun-Guey
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- Di- and tri-substituted s-triazine derivatives: Synthesis, characterization, anticancer activity in human breast-cancer cell lines, and developmental toxicity in zebrafish embryos
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Here we report on a small library based on a 4-aminobenzonitile-s-triazine moiety. We used a straightforward orthogonal synthetic pathway to prepare di- and tri-substituted s-triazine derivatives, whose basic structure was modified. The newly synthesized compounds were fully characterized by 1H NMR, 13C NMR and elemental analysis. They showed strong anticancer activity against two human breast cancer cell lines (MIDA-MB-231 and MCF-7), with IC50 values less than 1 μM. These s-triazine compounds were generally more selective towards hormone receptor-positive breast cancer cell line MCF-7 than the triple negative MDA-MB-231 cell line. Zebrafish embryos were used to test the developmental toxicity of the target compounds in vivo. The phenotype of embryos treated with the derivatives resembled that of those treated with estrogen disruptors. This observation strongly supports the notion that that these compounds induce their anticancer activity in human breast cancer cells via targeting the estrogen and progesterone receptors.
- El-Faham, Ayman,Farooq, Muhammad,Almarhoon, Zainab,Alhameed, Rakia Abd,Wadaan, Mohammad A.M.,de la Torre, Beatriz G.,Albericio, Fernando
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- Glass engineering of aminotriazine-based materials with sub-ambient: T gand high kinetic stability
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A challenge in glass engineering is the design of molecular glasses combining a high glass kinetic stability (GS) of the amorphous phase with a low (sub-ambient) glass transition temperature (Tg). Triazine derivatives with arylamino substituents readily form glassy phases that can show outstanding resistance to crystallization. In the present study, a series of 12 analogous compounds incorporating phenylamino and cyclohexylamino groups was synthesized, and their thermal properties and intermolecular interactions were studied. All compounds possess an excellent glass-forming ability, a low Tg ranging from 32 °C to as low as -19 °C, and a high GS. While the cyclohexyl derivatives show higher Tg, the phenyl derivatives possess a higher GS with some compounds remaining completely amorphous for over three years despite their sub-ambient Tg. X-ray diffraction, infrared spectroscopy and DFT calculations reveal that the higher volume occupancy and rotational energy barrier of cyclohexyl groups are the main factors responsible for the compounds' higher Tg values but that they also contribute to their higher propensity to crystallize. In counterpart, the planarity of phenyl groups leads to poorer packing and enhances their GS while keeping their Tg well below ambient. The formation of hydrogen bonds or competing interactions provides an additional handle to tune the Tg of the compounds. Taken together, these studies provide guidelines for the design of molecular glasses with readily tunable thermal properties in view of their functionalization. This journal is
- Iankovitch, Anna,Jokar, Mahboubeh,Kara Ali, Zeinab,Lebel, Olivier,Maris, Thierry,Pellerin, Christian
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p. 4275 - 4288
(2020/07/10)
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- Design, Synthesis and Biological Evaluation of Novel Nonsteroidal Progesterone Receptor Antagonists Based on Phenylamino-1,3,5-triazine Scaffold
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We report here the development of phenylamino-1,3,5-triazine derivatives as novel nonsteroidal progesterone receptor (PR) antagonists. PR plays key roles in various physiological systems, including the female reproductive system, and PR antagonists are promising candidates for clinical treatment of multiple diseases. By using the phenylamino-1,3,5-triazine scaffold as a template structure, we designed and synthesized a series of 4-cyanophenylamino-1,3,5-triazine derivatives. The synthesized compounds exhibited PR antagonistic activity, and among them, compound 12n was the most potent (IC50=0.30μM); it also showed significant binding affinity to the PR ligand-binding domain. Docking simulation supported the design rationale of the compounds. Our results suggest that the phenylamino-1,3,5-triazine scaffold is a versatile template for development of nonsteroidal PR antagonists and that the developed compounds are promising lead compounds for further structural development of nonsteroidal PR antagonists.
- Kaitoh, Kazuma,Nakatsu, Aki,Mori, Shuichi,Kagechika, Hiroyuki,Hashimoto, Yuichi,Fujii, Shinya
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p. 566 - 575
(2019/07/22)
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- Design and synthesis of mono-and di-pyrazolyl-s-triazine derivatives, their anticancer profile in human cancer cell lines, and in vivo toxicity in zebrafish embryos
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s-Triazine is considered a privileged structure, as it is found in several FDA-approved drugs. In the framework of our ongoing medicinal chemistry project based on the use of s-triazine as a scaffold, we synthesized a series of mono- and di-pyrazolyl-s-triazine derivatives and tested them against four human cancer cell lines, namely Human breast carcinoma (MCF 7 and MDA-MB-231), hepatocellular carcinoma (HepG2), colorectal carcinoma (LoVo), and leukemia (K562). The cell viability assay revealed that most of the s-triazine compounds induced cytotoxicity in all four types of human cancer cell lines, however, compounds 4a, and 6g, both of them have a piperidine moiety in their structure were most effective. These two compounds affected the cell viability of cancer cells, with IC50 values within the range between 5 to 9 μM. The cell cycle analysis showed that 4a and 6g induced S and G2/M phase cell cycle arrest in K562 cells. This could be the mechanism by which these molecules induced cytotoxicity in tested cancer cells. The prepared compounds were tested in zebrafish embryos to evaluate in vivo and developmental toxicity of the pyrazolyl-s-triazine derivatives in animals. None of the derivatives were lethal in the concentration range tested.
- Farooq, Muhammad,Sharma, Anamika,Almarhoon, Zainab,Al-Dhfyan, Abudalla,El-Faham, Ayman,Taha, Nael Abu,Wadaan, Mohammad A.M.,Torre, Beatriz G. de la,Albericio, Fernando
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p. 457 - 464
(2019/03/27)
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- Synthesis method and application of naphthalimides derivatives containing cyanuric chloride
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The invention discloses synthesis and application of naphthalimides derivatives containing cyanuric chloride, and belongs to the field of biological organic synthesis. According to the invention, a cyanuric chloride derivative is introduced onto a naphthalimides parent, so that the drug tolerance can be effectively avoided, and an antitumour effect is improved. According to the naphthalimides derivatives containing cyanuric chloride, different cyclic amine groups are used for replacing Br at the tail end of anhydride naphthalene, and the structure-function relationship of pharmaceutical molecules is researched; cyanuric chloride is modified by different aliphatic amine, aromatic amine or alcohol, and the structure-function relationship of pharmaceutical molecules is researched; aminoethylpiperazine is taken as a bridge chain to connect the modified anhydride naphthalene with the naphthalimides derivatives through substitution reaction, and the novel naphthalimides derivatives containing cyanuric chloride is formed through synthesis and has the antitumour effect.
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Paragraph 0047; 0049; 0050; 0051; 0052; 0059; 0061; 0062
(2018/04/03)
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- Understanding the effect of an amino group on the selective and ultrafast detection of TNP in water using fluorescent organic probes
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We have designed and developed three single-molecule fluorescent probes differing in the number of amino groups, namely 5-((4,6-Diamino-1,3,5-triazin-2-yl)amino)isophthalic acid (H2ATAIA, 1), 5-((4-amino-6-methoxy-1,3,5-triazin-2-yl)amino)isophthalic acid (H2AMTAIA, 2) and 5-((4,6-dimethoxy-1,3,5-triazin-2-yl)amino)isophthalic acid (H2DMTAIA, 3), from cheap and readily available starting materials via simple procedures in high yields for demonstrating their application in highly selective and ultrafast sensing of 2,4,6-trinitrophenol (TNP) in water (slurry mode). Probes 1-3 have been characterized by various analytical techniques, such as melting point, FTIR, UV-vis and NMR (1H and 13C) spectroscopy and high resolution mass spectrometry (HRMS). It is quite evident that the effect of an amino group is more prominent compared to a methoxy group towards the selective detection of TNP over other potentially interfering nitro compounds. The detection limit for the diamino derivative was found to be 120 ppb compared to those with one amino or no amino group (0.8 ppm and 1.2 ppm, respectively). We also report the ideal real time detection of TNP through a contact mode or instant spot via paper strips. Spectral overlap, time-resolved fluorescence studies, quantum yield, Stern-Volmer plots, field emission scanning electron microscopy (FESEM) and DFT calculations have been used to establish their mechanism of action. Furthermore, competitive nitro-analyte tests demonstrate that the selectivity for TNP is more in 1 compared to 2 and 3. To the best of our knowledge, we have demonstrated for the first time molecular decoding of TNP based on the dual read-out identification scheme constructed from life-time and quantum yield. These probes have been found to be highly photostable in the presence of acidic TNP as well as recyclable without much loss of sensitivity up to five cycles. These results vividly depict that these are excellent candidates for environmental monitoring.
- Das, Prasenjit,Mandal, Sanjay K.
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p. 3288 - 3297
(2018/04/05)
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- A robust multifunctional ligand-controlled palladium-catalyzed carbonylation reaction in water
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A novel, hydrophilic and recyclable methoxypolyethylene glycol (PEG)-modulated s-triazine-based multifunctional Schiff base/N,P-ligand L9 was prepared and used in Pd-catalyzed Heck-type carbonylative coupling reactions, affording diverse chalcone derivatives and 1,4-dicarbonyl esters in good yields.
- Gao, Pei-Sen,Zhang, Kan,Yang, Ming-Ming,Xu, Shan,Sun, Hua-Ming,Zhang, Jin-Lei,Gao, Zi-Wei,Zhang, Wei-Qiang,Xu, Li-Wen
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supporting information
p. 5074 - 5077
(2018/05/26)
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- Design and synthesis of 1,3,5-triazine derivatives as novel inverse agonists of nuclear retinoic acid receptor-related orphan receptor-γ
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1,3,5-Triazine structure is a versatile chemical species for development of functional molecules, including biologically active compounds. We report herein the design, synthesis and biological evaluation of novel inverse agonists of nuclear retinoic acid receptor-related orphan receptor-γ (RORγ), in which the 2-anilino-1,3,5-triazine moiety was used as a scaffold for structural development. Among the synthesized compounds, 13b exhibited potent and selective inverse agonistic activity toward RORγ, being more potent than the lead compound T0901317 (7). The results suggest that the 2-anilino-1,3,5-triazine moiety is a useful scaffold for development of inhibitory ligands of nuclear receptors.
- Kaitoh, Kazuma,Toyama, Hirozumi,Hashimoto, Yuichi,Fujii, Shinya
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p. 547 - 556
(2019/05/21)
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- Pharmaceutically acceptable salt of benzocoumarin derivative, and preparation method and application thereof
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The invention provides a pharmaceutically acceptable salt of a benzocoumarin derivative, and a preparation method and an application thereof, belonging to the field of medicinal chemistry. According to the invention, the preparation method has the advantages of simplicity, easily available raw materials and convenient aftertreatment; and the target compound provided by the invention has high synthetic yield and purity, wherein the purity is up to 98% or above, and the structure of the compound passes verification of nuclear magnetism and mass spectrometry. Pharmacological activity screening experiment results show that the compound with a novel structure displays extremely strong cytotoxic activity on human hepatoma cell line HepG2, and the compound has a minimum IC50 value reaching 7.85 [mu]M and provides important values for further development of benzocoumarin antitumor drugs.
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Paragraph 0064; 0065; 0066
(2017/08/28)
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- Rearrangement products in aqueous photolysis of thifensulfuron methyl
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Photo-degradation of [14C]-thifensulfuron methyl has been investigated in aqueous media using a light source which simulates sunlight. Degradation of thifensulfuron methyl proceeds predominantly via sulfonylurea bridge ipso-contraction, and via cleavage of the bridge structure, to yield products in which the thiophene and the triazine rings have disconnected. One significant degradation product, which accounts for nearly 10%, retained both rings with truncated bridge moiety. Surprisingly, this product had thiophene ring substituents rearranged from their original locations. Other laboratories have reported photodegradation of thifensulfuron-methyl, and identified similar degradation products as well. The structure of the rearrangement product has been misidentified in previous reports because the rearrangement of the thiophene ring is not widely recognized. An unambiguous identification of this product and potential rearrangement mechanisms are presented in this report.
- Sharma, Ashok K.,Ryan, David L.,Marr, Nina L.,Wadsley, Michael P.,Cheatham, Steve F.
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p. 401 - 410
(2017/06/29)
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- Hydrazino-methoxy-1,3,5-triazine derivatives' excellent corrosion organic inhibitors of steel in acidic chloride solution
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The corrosion inhibition performance of 2-hydrazino-4,6-dimethoxy-1,3,5-tirazine (DMeHT), 2,4-dihydrazino-6-methoxy-1,3,5-triaizine (DHMeT), and 2,4,6-tridydrazino-1,3,5-triaizne (TH3 ) on steel corrosion in acidic media was examined using electrochemical techniques. The results showed 2,4-Ddihydrazino-6-methoxy-1,3,5-triaizine (DHMeT) gave the best corrosion protection performance among the other hydrazino derivatives even at a low concentration of 25 ppm (95%). The number of hydrazino groups play an important role in the corrosion inhibition, where the two hydrazine groups increased the electrostatic interactions between the protonated tested compounds, the negatively charged steel surface resulted from the adsorption of the chloride anions, and the presence of the methoxy group made the compound more reliable for formation of film protection on the surface of steel through the lone pair of oxygen atoms. Electrochemical Impedance Spectroscopy (EIS) measurements suggested that the corrosion process of steel in presence of the hydrazino-s-triazine derivatives (TH3 , DMeHT and DHMeT) were being controlled by the charge transfer reaction. Polarization curves indicated that the examined TH3 , DMeHT and DHMeT behaved as mixed type inhibitors.
- El-Faham, Ayman,Osman, Sameh M.,Al-Lohedan, Hamad A.,El-Mahdy, Gamal A.
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- Sigma-spacer regulated thiophenyl triazine conjugates: Synthesis and crystal, electronic and luminescent properties
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A water-accelerated Pd catalyzed Suzuki-Miyaura cross-coupling reaction was developed for the synthesis of thiophenyl triazine conjugates (TTCs). The compounds (2a-2e and 3a-3e) with five σ-spacers were obtained and fully characterized. The X-ray analysis of 2a, 2d, and 3d found that the length of the intermolecular H bond was 3.465(3) ? and the π-π interactions ranged from 3.6538(2)-3.9519(1) ?. Five σ-spacers of TTCs had an effect on their emissions from blue (363 nm) to yellow (530 nm) whilst 2- and 3-thiophenyl chromophores finely tune the emission from 530 to 504 nm. The DFT computation showed the TTCs had low HOMO (-6.8 eV) and LUMO (-2.5 eV) energy and high triplet energy (ET, 2.4 eV). The energy level and gap of TTCs were regularly modulated by the σ-spacer.
- Zhu, Zhuangli,Shao, Ersha,Xu, Shan,Sun, Huaming,Zhang, Guofang,Xie, Zunyuan,Zhang, Weiqiang,Gao, Ziwei
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p. 76883 - 76889
(2016/08/30)
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- MK2 INHIBITORS AND USES THEREOF
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The present invention provides compounds, compositions thereof, and methods of using the same.
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Paragraph 0305
(2016/04/09)
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- Ultrasonic promoted synthesis of novel s-triazine-Schiff base derivatives; molecular structure, spectroscopic studies and their preliminary anti-proliferative activities
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Novel series of s-triazine-Schiff base derivatives were synthesized employing ultrasonic irradiation and characterized by NMR (1H and 13C), FT-IR, and elemental analysis. The use of ultrasonic irradiation has allowed the preparation of the target products with better yields in shorter reaction time and excellent purities compared to the conventional heating. X-ray single crystal diffraction experiments verified the molecular structure of four from the new prepared s-triaizne-Schiff base derivatives. The molecular structures of the studied compounds are computerized using DFT/B3LYP method. The effects of substituent at the triazine and phenyl ring on the electronic and spectroscopic properties of the studied compounds were also investigated. The natural atomic charges showed that pipridino-s-triazine derivatives are richer in electrons than those having morpholino derivatives. The anti-proliferative effects for the prepared compounds were tested against three different cancer cell lines.
- El-Faham, Ayman,Soliman, Saied M.,Ghabbour, Hazem A.,Elnakady, Yasser A.,Mohaya, Talal A.,Siddiqui, Mohammed R.H.,Albericio, Fernando
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p. 121 - 135
(2016/07/07)
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- Dioxouranium complexes with pentadentate s-triazine Schiff base ligands: Synthesis, crystal structure and optical properties
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Using the reactions of 2,4-dihydrazino-(R)-s-triazine (R – methoxy (DHMT)) with salicylaldehyde and o-vanillin ligands 2,4-Bis(2-hydroxybenzylidenehydrazino)-6-methoxy-s-triazin (L1) and 2,4-Bis(2-hydroxy-3-methoxybenzylidenehydrazino)-6-methoxy-s-triazin (L2) were obtained. Using the reaction of 2,4-dihydrazino-(R)-s-triazine (R – amino (DHAT)) with o-vanillin ligand 2,4-Bis(2-hydroxy-3-methoxybenzylidenehydrazino)-6-amino-s-triazine (L3) was obtained. By the reactions of the prepared ligands, derivatives of hydrazo-s-triazine, with uranyl acetate or nitrate, three new complexes were prepared. X-ray diffraction shows that the UO22+ion is in a pentagonal bipyramidal coordination environment. Two oxygen atoms of the UO22+ion occupy the axial positions and three atoms of nitrogen and two atoms of oxygen construct the equatorial plane. The uranyl(VI) complexes were characterized by single-crystal X-ray diffraction, UV–vis, fluorescence and IR spectroscopy. Thermal stabilities of the complexes were investigated using thermogravimetric analysis.
- Pavelek, Lubomír,Ladányi, Vít,Ne?as, Marek,Vallová, Silvie,Wichterle, Kamil
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- Synthesis of new strobilurin derivatives with modified 1,3,5-triazine moiety
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A new procedure for the synthesis of a series of strobilurin derivatives is reported. The new compounds bear the 1,3,5-triazine ring structure and can be used as the potential fungicide. All target compounds had been identified by 1H NMR spectrum, IR spectrum and HRMS. The results of antifungal activities showed that all target compounds exhibited antifungal activities against three fungus strains at the concentration 20 μg/mL.
- Yang, Xiu,Zhang, Yao-Lei,Wang, Yu-Liang,Chen, Tian,Luo, Juan
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p. 8897 - 8900
(2013/11/19)
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- AQUEOUS PIGMENT DISPERSION, AND AQUEOUS INK FOR INKJET RECORDING
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[Problem] To provide an aqueous ink for inkjet recording, which realizes excellent ink ejection properties, tinctorial strength, and image fastness. [Means for Resolution] An ink containing a pigment dispersion containing A and B, and an aqueous medium: A: an azo pigment represented by the following formula (1) and having at least one characteristic peak at Bragg angles (20) of 5 to 15° and 20 to 30° in X-ray diffraction with characteristic Cu Kα line; and B: a vinyl polymer containing a hydrophobic structural unit (a) and a hydrophilic structural unit (c).
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Page/Page column 55
(2012/07/27)
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- AQUEOUS PIGMENT DISPERSION, AND AQUEOUS INK FOR INKJET RECORDING
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To provide an aqueous ink for inkjet recording, which realizes excellent ink ejection properties, tinctorial strength, and image fastness using an aqueous pigment dispersion. An aqueous pigment dispersion containing A and B, wherein A is an azo pigment represented by the following formula and in a crystal form having at least one characteristic peak at Bragg angles (2θ) of 5 to 15° and 20 to 30° in. X-ray diffraction with characteristic Cu Ka line, a tautomer, a salt or hydrate thereof; and B is a vinyl polymer containing a specific structural unit, a structural unit derived from a salt-forming group-containing monomer (a), and a structural unit derived from a monomer selected from a styrene series macromer (b) and a hydrophobic monomer (c), provided that the water-insoluble vinyl polymer has at least either of 2 or more hydroxyl groups and 1 or more carboxyl groups at the end of the main chain:
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Page/Page column 47
(2012/07/27)
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- Synthesis and structure of oxacalix[2]arene[2]triazines of an expanded π-electron-deficient cavity and their interactions with anions
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Novel macrocyclic anion receptors based on the principle of anion-π interactions were reported. By means of both post-macrocyclization modification protocol and the stepwise fragment coupling approach, functionalized oxacalix[2]arene[2]triazines bearing two other electron-deficient (hetero)aromatic rings on the lower rim were efficiently synthesized. The resulting oxacalix[2]arene[2]triazine macrocyclesadopt 1,3-alternate conformation, yielding therefore an expanded electron-deficient cavity or space consisting of two triazine rings and two appending aromatic rings. Spectroscopic titration study showed the selective interaction of the pentafluorophenyl- substituted oxacalix[2]arene[2]triazine with azide and fluoride in solution with the binding constants (K1:1) ranging from 1.33 × 10 3 to 3.52 × 103 M-1.
- Li, Sen,Fa, Shi-Xin,Wang, Qi-Qiang,Wang, De-Xian,Wang, Mei-Xiang
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supporting information; scheme or table
p. 1860 - 1867
(2012/04/23)
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- Synthesis and functionalization of heteroatom-bridged bicyclocalixaromatics, large molecular triangular prisms with electron-rich and -deficient aromatic interiors
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The synthesis and functionalization of oxygen and nitrogen atom bridged bicyclocalixaromatics of triangular prism structures are reported. By means of a fragment coupling approach, molecular triangular prisms of electron-rich and electron-deficient aromatic interiors were prepared using 1,3,5-tri(p- hydroxyphenyl)benzene and 2,4,6-tri(p-aminophenyl) triazine as base units and chlorotriazines as pillars. Aromatic nucleophilic substitution reaction of chlorotriazine moieties with functionalized amines led to triangular prisms with functionalizations on the peripheral edge positions, while functionalized triangular prisms on the vertex nitrogen positions were obtained using 2,4,6-tri[(p-allylamino)phenyl]-triazine derivative as a starting material. Symmetrical and distorted molecular triangular prisms in the solid state were revealed by X-ray crystallography. As evidenced by NMR spectroscopic data, however, all cage molecules synthesizedmost probably adopted highly symmetric triangular prism structures in solution phase. The functionalized shape-persistent triangular prism structures might find applications in molecular recognition and in the construction of higher and more sophisticated molecular architectures in supramolecular chemistry.
- Naseer, Muhammad Moazzam,Wang, De-Xian,Zhao, Liang,Huang, Zhi-Tang,Wang, Mei-Xiang
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supporting information; experimental part
p. 1804 - 1813
(2011/06/10)
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- AZO PIGMENT, PROCESS FOR PRODUCING AZO PIGMENT, DISPERSION CONTAINING AZO PIGMENT, AND COLORING COMPOSITION
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There is provided an azo pigment having excellent coloring characteristics such as coloring power and stable particle size thereof even with the lapse of time, and showing excellent stability as a pigment dispersion and excellent stability as an ink liquid. There is also provided a pigment dispersion showing excellent coloring characteristics, storage stability of dispersions, and ink liquid stability by dispersing the pigment of the invention in various media. An azo pigment represented by the following formula (1) and having characteristic peaks at Bragg angles (2θ±0.2°) of 7.5°, 25.8°, and 26.9 in X-ray diffraction with characteristic Cu Kα line, and a tautomer thereof.
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Page/Page column 35
(2011/07/07)
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- AZO PIGMENT, METHOD FOR PRODUCING AZO PIGMENT, DISPERSION CONTAINING AZO PIGMENT, AND COLORING COMPOSITION
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There is provided an azo pigment having excellently good color reproducibility, dispersibility, and storage stability of pigment dispersions and having excellent hue and tinctorial strength. An azo pigment represented by the following formula (1) and having characteristic peaks at Bragg angles (28:f::0.2°) of 7.2,p, 13.4°, 15.0°, and 25.9 in X-ray diffraction with characteristic Cu Kα line, and a tautomer thereof:
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Page/Page column 17
(2011/10/12)
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- YELLOW PIGMENT MIXTURE DISPERSION FOR INKJET RECORDING
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A yellow pigment dispersion is provided the yellow pigment dispersion including: a coloring agent that contains at least one of an azo pigment represented by following formula (1) and a tautomer of the azo pigment, and at least one pigment selected from the group consisting of C.I. Pigment Yellow 1, 2, 3, 12, 13, 14, 16, 17, 73, 74, 75, 83, 93, 95, 97, 98, 109, 110, 114, 120, 128, 138, 139, 150, 151, 154, 155, 180, 185 and 213.
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Page/Page column 36; 38
(2010/10/03)
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- Color composition for color filter, method for preparing it, and color filter
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A color composition for color filter is provided, the color composition for color filter including: at least one of an azo pigment represented by formula (1), a tautomer of the azo pigment, and salts or hydrates thereof: wherein Y represents a hydrogen atom or a substituent; W represents an alkoxy group, an amino group, an alkyl group or an aryl group; G represents a hydrogen atom, an alkyl group, a cycloalkyl group, an aralkyl group, an alkenyl group, an alkynyl group, an aryl group or a heterocyclic group; X1 and X2 each independently represents a hydrogen atom, an alkyl group, an acyl group, an alkylsulfonyl group or an arylsulfonyl group; R1 represents a hydrogen atom or a substituent; R2 represents a heterocyclic group; and n represents an integer of from 1 to 4.
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Page/Page column 33
(2010/10/03)
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- Synthesis of polynuclear heterocyclic polynitrogen systems based on cyanuric chloride and its derivatives
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Polynuclear structures containing several heterocycles of various types were synthesized by the reaction of cyanuric chloride and its mono- and dichloro derivatives with triazoles and tetrazoles in the presence of bases.
- Vereshchagin,Verkhozina,Pokatilov,Proidakov,Kizhnyaev
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experimental part
p. 206 - 211
(2011/08/05)
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- Novel dialkoxytriazine-type glycosyl donors for cellulase-catalysed lactosylation
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Novel glycosidic compounds, 4,6-dialkoxy-1,3,5-triazin-2-yl β-lactosides (DAT-β-Lac), have been prepared directly in water from lactose. The reaction was carried out on a laboratory scale without protecting the hydroxy groups of lactose. The resulting triazine derivatives were found to be recognized by endo-β1,4-glucanase III from Trichoderma reesei (EGIII). The EGIII-catalysed transglycosylation of 4,6-dimethoxy-1,3,5-triazine derivative (DMT-β-Lac) with various glycosyl acceptors has successfully been demonstrated, affording the corresponding lactosylated products.
- Tanaka, Tomonari,Noguchi, Masato,Watanabe, Kazuhito,Misawa, Takuya,Ishihara, Masaki,Kobayashi, Atsushi,Shoda, Shin-Ichiro
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experimental part
p. 5126 - 5132
(2010/12/25)
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- Synthesis of aza-bridged calix(4-methoxy)triazines toward flattened π-conjugated macrocycles
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Calixtriazines containing a 4-alkoxy-1,3,5-triazine backbone were efficiently synthesized by sequential fragment coupling started from 4-alkoxy-2,6-dichrolo-1,3,5-triazine. These macrocycles tend to form flattened conformations, leading to a stable π-conjugated system, presumably due to the electronic features of the alkoxy-substituent on the triazine rings.
- Tanaka, Hiroyuki,Wada, Ayako,Shiro, Motoo,Hioki, Kazuhito,Morisaki, Daiki,Kunishima, Munetaka
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experimental part
p. 609 - 616
(2009/12/07)
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- High-energy 1,3,5-triazinyl diazenes, and process thereof
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A compound possesses the chemical structure of: wherein n is greater than zero. The compound is useful in energetic composition, particularly in linear, branched, dendritric, oligomer and cyclic oligomer azo-triazine forms.
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Page/Page column 9
(2008/12/06)
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- Spectral characterization of selected stilbentriazine dyes - Structural trans-cis isomerisation
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The paper deals with the spectral investigations of new stilbentriazine dyes containing amino groups or alkoxy group attached to the main molecular triazine ring. Absorption and fluorescence spectra of the dyes in aqueous solutions were recorded. The existence of two spectral structures absorbing at 275 and 350 nm was shown and they are assigned to cis- and trans- structures of dyes, respectively. It was indicated that absorption and fluorescence features of the dyes are not significantly affected by a kind of substituent; exception is ST2 which differs in molecular structure and in the absorption and emission properties from the remaining dyes. The quantum yields of dye fluorescence and the yields of cis-trans energy transfer were also evaluated. The influence of temperature, solution pH and radiation exposure on photoproperties of the dye spectral forms were also examined. The large impact of the radiative exposure time on molecular conformation changes was observed, whereas temperature and environmental pH do not affect the dye spectral parameters. The equilibrium ratios of the trans- to cis- structures were estimated.
- Hanyz,Ion,Nuta,Wróbel
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experimental part
p. 165 - 171
(2009/02/06)
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- TRIAZINES SUITABLE FOR USE IN FABRIC TREATMENT COMPOSITIONS
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A water-soluble, triazine-based, non-dye, cellulose cross-linking agent that has a highly flexible linking group between at least two, mono-reactive cross-linking moieties and further hydrophilic or non-hydrophilic substituents, being preferrably represented by the general formula (I): (R1)(X1)T-L1-B-T(X2)(R2) wherein: R1 et R2 are cellulose-unreactive substituent groups on the s-triazine (T) and may be the same or different, X1 and X2 are leaving groups on the s-triazine which are lost on reaction with cellulose and may be the same or different, L1 et L2 are linking groups, an may be the same or different or absent, B is the bridging group comprising or consisting of at least one aliphatic polyoalkylene chain.
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Page/Page column 21-22
(2010/02/15)
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- CERTAIN AROMATIC MONOCYCLES AS KINASE MODULATORS
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Compound having Formula (I): wherein (W) is a monocyclic ring having the structure are useful as modulators of kinase activity.
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- Electroluminescence from a new distyrylbenzene based triazine dendrimer
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We have synthesised a new distyrylbenzene cored dendrimer which utilises triazine rings to link the surface groups. It was found that methoxy surface groups were sufficient to give the dendrimer good solubility and good quality thin films could be prepared by spin-coating from solution. The dendrimer was luminescent both in solution and the solid state with the emission occurring from the core. The photoluminescence quantum yield was determined to be 31±3% in the solid state. The dendrimer was incorporated into a single layer light-emitting diode (ITO/dendrimer/Ca) and was found to emit blue light with an external quantum efficiency of 0.003%.
- Lupton, John M.,Hemingway, Leon R.,Samuel, Ifor D.W.,Burn, Paul L.
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p. 867 - 871
(2007/10/03)
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- Reactive dyestuffs containing a triazinylamino group and one or two groups of the vinylsulfone series
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Fiber-reactive dyestuffs, such as, for example, azo dyestuffs and heavy metal complex derivatives thereof, anthraquinone dyestuffs, phthalocyanine dyestuffs and formazan dyestuffs, which contain a fiber-reactive group of the vinylsulfone series and furthermore a group of the general formula STR1 in which Rx is hydrogen or lower alkyl, which can be substituted by substituents customary in dyestuffs, and Q1 and Q2 both independently of one another are each lower alkyl, which is substituted by 1 or 2 lower alkanoyl groups or 1 or 2 lower alkoxycarbonyl groups or by one such alkoxycarbonyl and alkanoyl group, or an amino group, which is substituted by optionally substituted aryl and/or alkyl radicals, or an optionally substituted alkoxy, aryloxy, alkylthio or arylthio radical or a cyanamido radical, are described. The novel dyestuffs dye material containing hydroxy and/or carboxamide groups, such as cellulose fiber materials, wool and polyamides, in deep shades, and moreover are suitable for discharge and resist printing.
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- Cuprophthalocyanine type compounds
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A cuprophthalocyanine type compound represented by formula [1] in the form of free acid STR1 (wherein D is a cuprophthalocyanine radical; B is an alkylene group of 2 to 4 carbon atoms or a phenylene group which may have one or two carboxyl group(s) or sulfonic acid group(s) as a substituent(s); R is a lower alkyl group or a lower alkoxy-lower alkyl group; X is a carboxyl group or a carbamoyl group and combines with the 3- or 4-position of the pyridine ring; l is 1, 2 or 3; m is 0, 1 or 2; n is 1 or 2; and the sum of l, m and n is 2, 3 or 4) as well as a method for dyeing cellulosic fiber materials using the said compounds.
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- IMPROVEMENT OF THE SELECTIVITY OF ALKOXYLATION OF CYANURIC CHLORIDE.
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Study of the quantitative relationships of the alkoxylation reaction and optimization of the complex reaction based on a mathematical model show that individual monoalkoxy-s-triazines free from 5-15% of dialkoxy-s-triazines cannot be obtained in aqueous acetone solutions. It is found that if the reaction is conducted in the basic bipolar aprotic solvent dimethylacetamide it proceeds selectively with exclusive formation of monoalkoxy-s-triazines. It can be seen from the data that the nature of the solvent does not affect selectivity of the reaction significantly. It is shown that when cyanuric chloride reacts with amides left bracket dimethylformamide (DMFA), N-methylformamide right bracket hygroscopic hydrolytically unstable products of the salt type are formed. The intermediates react with nucleophiles, such as aniline, to form substituted triazines. The reaction proceeds analogously with alcohols, and the hydrogen chloride evolved is bound irreversibly by dimethylacetamide.
- Koryakov,Koshokov,Nikitin,Marchukov,V'yunov
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p. 1309 - 1310
(2007/10/02)
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- Phenolic-1,3,5-triazines
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Novel oligomeric and polymeric phenolic 1,3,5-triazines, for example those of the formula STR1 their preparation and their use for stabilizing organic material and also the organic material protected against oxidative and light-induced degradation with the aid of these compounds.
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- Organic Peroxides. Part 12. The Preparation and Properties of Some Triazinyl Peroxides
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The triazinyl peroxides (A; X=Y=OOBut; X=OMe, Y=OOBut; X=Y=OMe; X=NEt2, Y=OOBut; X=Y=NEt2) and (B) have been prepared from the reaction between the appropriate peroxidic nucleophile and chlorotriazine.The structures of the peroxides are confirmed by their 13C n.m.r. spectra, and by the recovery of t-butyl hydroperoxide when the peroxides (A; X=Y=OOBut; X=OMe, Y=OOBut) were hydrolysed. .These peroxides are thermally stable up to ca. 90 deg C.Photolysis of the peroxides (A) gives the radical ButO. and XYC3N3O..The e.s.r. spectra of the triazinoxyl radicals could not be observed, but the adducts XYC3N3OCH2CH2. and XYC3N3OP.(OMe)3, which they form with ethylene and with trimethyl phosphite, respectively, were detected.It is suggested that these properties imply that the radicals have a ?-O rather than a ?-delocalised structure.
- Davies, Alwyn G.,Sutcliffe, Roger
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p. 1512 - 1519
(2007/10/02)
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