3638-04-8Relevant articles and documents
Synthesis and characterization of lanthanide complexes with a pentadentate triazine-based ligand
Pavelek, Lubomír,Ladányi, Vít,Ne?as, Marek,Moravec, Zdeněk,Wichterle, Kamil
, p. 134 - 141 (2016)
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.
Synthesis and antiproliferating activity of iron chelators of hydroxyamino-1,3,5-triazine family
Sun, Daekyu,Melman, Galina,LeTourneau, Nickolas J.,Hays, Allison M.,Melman, Artem
, p. 458 - 460 (2010)
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.
Inhibition of acetolactate synthase isozyme II from Escherichia coli by a new azido-photoaffinity sulfonylurea
Ortega, Florence,Bastide, Jean
, p. 261 - 274 (1997)
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.
Triazine based Mn (II) and Mn (II)/Ln (III) complexes: Synthesis, characterization and catecholase activities
Celik, Derya,Kose, Muhammet
, (2019)
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.
A highly emissive fluorescent Zn-MOF: molecular decoding strategies for solvents and trace detection of dunnite in water
Das, Prasenjit,Mandal, Sanjay K.
, p. 21274 - 21279 (2018)
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.
Two heptacoordinated manganese(II) complexes of giant pentadentate s-triazine bis-Schiff base ligand: Synthesis, crystal structure, biological and DFT studies
Soliman, Saied M.,El-Faham, Ayman,Elsilk, Sobhy E.,Farooq, Muhammad
, p. 275 - 285 (2018)
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.
Synthesis of Amidation Agents and Their Reactivity in Condensation Reactions
Sole, Roberto,Agostinis, Lodovico,Conca, Silvia,Gatto, Vanessa,Bardella, Noemi,Morandini, Andrea,Buranello, Chiara,Beghetto, Valentina
supporting information, p. 1672 - 1682 (2021/02/01)
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.
Synthesis and Antimicrobial Evaluation of Bis-morpholine Triazine Quaternary Ammonium Salts
Morandini, Andrea,Leonetti, Benedetta,Riello, Pietro,Sole, Roberto,Gatto, Vanessa,Caligiuri, Isabella,Rizzolio, Flavio,Beghetto, Valentina
supporting information, p. 3172 - 3176 (2021/08/03)
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.
Interfering with the Tumor-Immune Interface: Making Way for Triazine-Based Small Molecules as Novel PD-L1 Inhibitors
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
, p. 16020 - 16045 (2021/11/10)
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.
Synthesis and kinetic study of a series of chloro- and m-carboxypyridium triazinyl reactive dyes
Huang, Huei-Chin,Wu, Chun-Guey
, (2021/02/12)
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.
