1722-19-6Relevant academic research and scientific papers
Synthesis of 2-[2-(4-substituted-1,3,5-triazin-2-loxy)phenyl]-3,3-dimethoxypropanoate
Luo, Juan,Yang, Xiu,Wang, Yu-Liang,Wang, Yu-Zhong
, p. 2836 - 2840 (2015)
In this article, the synthesis of a series of novel compounds, methyl 2-[2-(4-substituted-1,3,5-triazin-2-yloxy)phenyl]-3,3-dimethoxypropanoate is reported. 4,6-Dichloro-N,N-diethyl-1,3,5-triazin-2-amine reacted with methyl 2-(2-hydroxyphenyl)-3,3-dimethoxypropanoate to give methyl 2-[2-{4-chloro-6-(diethylamino)-1,3,5-triazin-2-yloxy}phenyl]-3,3-dimethoxypropanoate, which then reacted with phenols or thiophenols to give nine novel targets compounds. The structures of target compounds had been characterized by IR, 1H NMR and HRMS.
Inter-ligand reactions: In situ formation of new polydentate ligands
Coxall, Robert A.,Harris, Steven G.,Henderson, David K.,Parsons, Simon,Tasker, Peter A.,Winpenny, Richard E. P.
, p. 2349 - 2356 (2000)
Two ligands have been synthesized by derivatisation of cyanuric chloride: 6-(diethylamino)-2,4-disulfanyl-1,3,5-triazine (H2SSta) 1 and 6-(diethylamino)-2-hydroxo-4-sulfanyl-l,3,5-triazine (H2OSta) 2 have been characterised by X-ray crystallography, which shows intermolecular hydrogen bonding in the solid state, leading to dimers of 1 and ribbons of 2. On reaction with metal salts both ligands undergo oligomerisation reactions. Compound 1 reacts with nickel chloride to form a mononuclear complex, [Ni{(Sta)S(S2ta)}] 3. In 3 two triazine ligands have reacted, to form a tetradentate ligand in which two triazine rings are bridged by a sulfur group, with a co-ordinated disulfide group present on one ring and a co-ordinated thiolate on the second. Compound 2 reacts with cobalt(ii) chloride to form a cage complex, [Co6NaO(OStaH)7{S(Ota)2}2(O 2CPh)2(H2O)2] 4. This complicated structure contains two polydentate ligands formed by linking triazine groups through a bridging sulfur. The cage contains four cobalt(n) and two cobalt(in) sites which are assigned by bond length considerations. The compound [Co(OSta)3] 5 co-crystallises with 4, and its structure has also been determined. The Royal Society of Chemistry 2000.
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
, p. 1672 - 1682 (2021)
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 conformational analysis of constrained ethylene-bridged bis(hydroxylamino-1,3,5-triazine) compounds as tetradentate ligands; structure of rigid dinuclear Ti(IV) complex
Hermon, Tal,Tshuva, Edit Y.
, p. 5953 - 5958 (2008)
(Chemical Equation Presented) Ethylene-bridged bis(hydroxylamino-1,3,5- triazine) compounds, that may serve as tetradentate ligands, were synthesized in three steps from 2,4,6-trichloro-1,3,5-triazine. These compounds demonstrate different rotation restrictions around the CAr-N bonds due to their distinctive electronic structure as apparent from their resonative contributors. A dinuclear complex Ti2(μ-L)2(OiPr)4 (L = bis(triazine)) was synthesized where each octahedral Ti(IV) center is also bound to two isopropoxo groups. The complex rigidity is manifested in a significant deviation from planarity of the aromatic systems, and relatively long Ti-N bonds compared to mononuclear analogous complexes. Increased ligand lability in this complex brings about diminished cytotoxicity toward colon and ovarian cells.
Microwave irradiation assists the synthesis of a novel series of bis-arm s-triazine oxy-schiff base and oxybenzylidene barbiturate derivatives
Dahlous, Kholood A.,Almarhoon, Zainab,Badjah-Hadj-Ahmed, Ahmed-Yacine,AL Othman, Zeid A.,El-Faham, Ayman
, (2018)
A novel series of s-triazines incorporating 4-hydroxybenzaldehyde and 4-hydroxy-3-methoxybenzaldehyde was prepared and fully characterized. The reaction was carried out via stepwise nucleophilic aromatic substitution of chlorine atoms in cyanuric chloride. The first chlorine was substituted by different amines (morpholine, piperidine, or diethylamine) to afford 2,4-dichloro-6-substituted-1,3,5-triazine. The second and third chlorines were substituted by benzaldehyde derivatives in the presence of Na2CO3 as a HCl scavenger to afford the target products: s-triazine oxyaldehyde derivatives (dipodal). The dipodal derivatives were reacted with acid hydrazide, hydralazine, barbituric, or thiobarbituric acid derivatives using conventional heating or microwave irradiation to afford the di-arm s-triazine oxy-Schiff base and oxybenzylidene barbiturate derivatives in good yields. Microwave irradiation done in less solvent afforded the target product in less reaction time with good yield and purity. These types of derivatives might have special interest in coordination and medicinal chemistry.
Docking, synthesis and antimalarial activity of novel 4-anilinoquinoline derivatives
Vijayaraghavan, Shilpa,Mahajan, Supriya
, p. 1693 - 1697 (2017/04/04)
A series of 4-anilinoquinoline triazine derivatives were designed, synthesized and screened for in vivo antimalarial activity against a chloroquine-sensitive strain of Plasmodium berghei. The compounds were further subjected to in vitro antimalarial activity against chloroquine-resistant W2 strain of Plasmodium falciparum and β-haematin inhibition studies. All the compounds exhibited in vivo antimalarial activity better than that shown by the standard drug, chloroquine. Twelve out of fifteen compounds showed better inhibition than that of chloroquine against chloroquine-resistant W2 strain of Plasmodium falciparum. Ten compounds showed β-haematin inhibition, better than that of chloroquine, with IC50 values in the range of 18–25?μM. One compound, 3k, was found to be better than artemisinin against W2 strain of Plasmodium falciparum and also displayed the best β-haematin inhibitory activity, thereby becoming eligible to be explored as a potential lead for antimalarial chemotherapy.
Synthesis and structure-activity relationship study of triazine-based inhibitors of the DNA binding of NF-κB
Fujii, Shinya,Kobayashi, Takanobu,Nakatsu, Aki,Miyazawa, Hiroshi,Kagechika, Hiroyuki
, p. 700 - 708 (2014/08/05)
Nuclear transcription factor nuclear factor-kappa B (NF-κB) has diverse pathophysiological functions, and NF-κ B inhibitors are considered to be candidates for multiple therapeutic applications. We previously reported a novel triazine-based NF-κB inhibitor, 2-anilino-4,6-dichloro-1,3,5- triazine (NI241), that directly inhibits DNA binding of NF-κB. Here, we report synthesis of a series of triazine derivatives and evaluation of their structure-activity relationships for NF-κB inhibition. We found that 2-amino-4,6-dichloro-1,3,5-triazine substructure is essential for the inhibitory activity of the lead compound NI241, and modification of NI241 by introduction of an m-methoxy substituent on the phenyl ring afforded the more potent derivative 28. The structure-activity relationships identified in this study suggested a possible mechanism of irreversible NF-κB inhibition by NI241, and should be helpful in the design of other NF-κB inhibitors.
Crown-linked dipyridylamino-triazine ligands and their spin-crossover iron(ii) derivatives: Magnetism, photomagnetism and cooperativity
Scott, Hayley S.,Ross, Tamsyn M.,Chilton, Nicholas F.,Gass, Ian A.,Moubaraki, Boujemaa,Chastanet, Guillaume,Paradis, Nicolas,Letard, Jean-Francois,Vignesh, Kuduva R.,Rajaraman, Gopalan,Batten, Stuart R.,Murray, Keith S.
, p. 16494 - 16509 (2013/12/04)
The syntheses, crystallography and magnetic properties of a series of compounds of formula trans-[FeII(L1)2(NCX) 2] (X = S, Se, BH3 (1-3)), cis-[FeII(L 2)(NCX)2]·CH2Cl2 (X = S, Se, BH3 (4-6)) and trans-[FeII(L3)(NCX) 2]n (X = S, Se (7-8)) are described (L1 = 6-chloro-N2,N2-diethyl-N4,N4- di(pyridin-2-yl)-1,3,5-triazine-2,4-diamine, L2 = 6,6′-(1,4,10,13-tetraoxa-7,16-diazacyclooctadecane-7,16-diyl)bis(N 2,N2-diethyl-N4,N4-di(pyridin-2-yl)- 1,3,5-triazine-2,4-diamine, L3 = 6,6′-(1,4,10,13-tetraoxa-7,16- diazacyclooctadecane-7,16-diyl)bis(N2,N2,N 4,N4-tetra(pyridin-2-yl)-1,3,5-triazine-2,4-diamine)). The magnetostructural properties of 1-8 have been probed in detail by variable temperature magnetic measurements and crystallographic methods. 1-6 display mononuclear structures while 7 and 8 form 1-D chain structures. Complexes 4-6 have the potential to form 1D-chains via L2 bridging, but instead form mononuclear complexes. Magnetic studies show that complexes 1, 2, and 4 remain in the high-spin (HS) state at all temperatures. An aged, dry, powdered sample of 3 gives an abrupt HS to LS transition (T1/2 = 200 K), while a freshly prepared, powdered sample of 3·1.5H2O displays thermal hysteresis (Δ = 7 K). Complexes 5, 6 and 7 undergo a gradual spin transition with T1/2 values of 100 K, 150 K and 130 K, respectively. Cooperativity parameters are compared, with 3 showing cooperativity (positive C) and 5 and 6 showing anticooperativity. Photomagnetic LIESST (light induced excited spin state trapping) studies were performed on complexes 5 and 6 and reveal T(LIESST) values lower than 60 K. An attempt has been made to understand the electronic structure of complex 3 and its cooperativity behaviour using density functional methods, the calculations reproducing the sign and, in part, the magnitude of the cooperativity.
Synthesis and antibacterial activity of some novel 4-benzyl-piperazinyl-s- triazine derivatives
Jana,Das
, p. 186 - 190 (2013/02/22)
Considerable interest has been attracted in s-triazine scaffold and its derivatives because of their large variety of pharmacological activities. In this project, a series of 4-benzyl-piperazinyl-s-triazine derivatives 5a to 5j were synthesized by three steps substitution reaction of cyanuric chloride with various nucleophilic compounds in presence of a base. Molecular structures of the synthesized compounds were elucidated by FTIR, 1H NMR, 13C NMR, MS spectral data and elemental analyses. The in vivo antibacterial activity was evaluated by broth dilution method against representative four Gram-positive and four Gram-negative bacterial strains. Many compounds have displayed comparable better antibacterial activity against Bacillus subtilis, Staphylococcus aureus, Staphylococcus epidermis and Pseudomonas aeruginosa with reference to streptomycin.
Design, synthesis and SAR exploration of hybrid 4-chlorophenylthiazolyl-s- triazine as potential antimicrobial agents
Gahtori, Prashant,Ghosh, Surajit K.
scheme or table, p. 281 - 293 (2012/07/13)
Two novel series of hybrid class 4-chlorophenylthiazole-s-triazine were synthesized via nucleophilic substitution of 2,4,6-trichloro-1,3,5-triazine with distinguished alkenyl/alkyl/aryl/hetero alkylaryl amino and mercapto nucleophiles under nitrogen atmosphere. We identified that the spectrums of antibacterial activity of all tested compounds reveal promising and significant inhibition of gram-positive and gram-negative micro-organisms and the most active compounds, 31d and 32d, were found to be non-toxic in preliminary cytotoxicity assay. We also report that the Molinspiration and Osiris Property Explorer calculations have found a new lead 32d, which binds preferentially to the nuclear receptor to exhibit antibacterial potency.
