19371-31-4Relevant articles and documents
Modification of the lead molecule: Tryptophan and piperidine appended triazines reversing inflammation and hyeperalgesia in rats
Kumari, Priya,Kaur, Sukhmeet,Kaur, Jashanpreet,Bhatti, Rajbir,Singh, Palwinder
, (2020)
The structural optimization of the molecules making them to fit into the active site pocket of COX-2 occupying the same space as covered by the natural substrate arachidonic acid helped in the emergence of compound 10 as an efficacious anti-inflammatory a
Convenient syntheses of cyanuric chloride-derived NHC ligands, their Ag(i) and Au(i) complexes and antimicrobial activity
Almalioti, Foteini,MacDougall, James,Hughes, Stephen,Hasson, Mohammed M.,Jenkins, Robert L.,Ward, Benjamin D.,Tizzard, Graham J.,Coles, Simon J.,Williams, David W.,Bamford, Sarah,Fallis, Ian A.,Dervisi, Athanasia
, p. 12370 - 12380 (2013)
Convenient syntheses of mono- and bis-imidazolium 1,3,5-triazine derivatives bearing piperidine and morpholine substituents are reported. In situ deprotonation of the mono-imidazolium salts and reaction with Ag2O or Au(tht)Cl (tht = tetrahydrothiophene) precursors affords the corresponding Ag(NHC)Cl and Au(NHC)Cl carbene complexes. In the presence of Ag(i) or Au(i) salts the bis-imidazolium pincers eliminate the imidazolium group to afford -OMe or -NMe2 substituted triazines depending on the solvent used. In solution, the Ag(i) and Au(i) complexes show a barrier to rotation about the Ctriazine-Namine bonds, with calculated ΔG ≠ barriers in the region of 70 kJ mol-1. Single crystal X-ray structures of several of the proligands and their corresponding Ag(i) and Au(i) complexes were obtained. These universally reveal an extended, rigidly planar π-conjugated network between the triazine core, imidazolium/ imidazolylidene substituents and exocyclic amine functions, to which the origin of the rotational barrier observed in solution is attributed. Only very weak Ntriazine-metal interactions are observed in the solid state, as indicated by small deviations of the CNHC-Ag-Cl bond angles from 180°and also supported by DFT calculations on the Ag(NHC)Cl complex (NHC = 4,6-dipiperidinyl-2-methylimidazolylidene triazine). Preliminary antimicrobial susceptibility studies against five microorganisms (methicillin resistant Staphylococcus aureus NCTC 13277, S. aureus NCTC 6571, Pseudomonas aeruginosa NCTC 10662, Proteus mirabilis NCTC 11938 and Candida albicans ATCC 90028) show that the above triazine-based Ag-NHC complexes are active antimicrobial and antifungal agents.
Design and synthesis of new s-triazine polymers and their application as nanoparticulate drug delivery systems
Khattab, Sherine N.,Abdel Naim, Samar E.,El-Sayed, Mousa,El Bardan, Aly A.,Elzoghby, Ahmed O.,Bekhit, Adnan A.,El-Faham, Ayman
, p. 9565 - 9578 (2016)
Herein, we report the synthesis of a library of new s-triazine polyamides containing glycine and thioglycolic acid. The reaction of s-triazine dicarboxylic acid derivatives with ethylenediamine, benzidine, piperazine, or p-phenylenediamine, afforded the t
Synthesis and preliminary biological evaluation of 1,3,5-triazine amino acid derivatives to study their MAO inhibitors
Khattab, Sherine N.,Khalil, Hosam H.,Bekhit, Adnan A.,El-Rahman, Mohamed Mokbel Abd,El-Faham, Ayman,Albericio, Fernando
, p. 15976 - 15988 (2015)
Three series of 4,6-dimethoxy-, 4,6-dipiperidino- and 4,6-dimorpholino-1,3,5-triazin- 2-yl) amino acid derivatives were synthesized and characterized. A preliminary study for their monoamine oxidase inhibitory activity showed that compounds 7, 18, and 25 had MAO-A inhibition activity comparable to that of the standard clorgyline, with apparently more selective inhibitory activity toward MAO-A than MAO-B and no significant acute toxicity.
(S)-4-(Difluoromethyl)-5-(4-(3-methylmorpholino)-6-morpholino-1,3,5-triazin-2-yl)pyridin-2-amine (PQR530), a Potent, Orally Bioavailable, and Brain-Penetrable Dual Inhibitor of Class i PI3K and mTOR Kinase
Rageot, Denise,Bohnacker, Thomas,Keles, Erhan,McPhail, Jacob A.,Hoffmann, Reece M.,Melone, Anna,Borsari, Chiara,Sriramaratnam, Rohitha,Sele, Alexander M.,Beaufils, Florent,Hebeisen, Paul,Fabbro, Doriano,Hillmann, Petra,Burke, John E.,Wymann, Matthias P.
, p. 6241 - 6261 (2019/07/04)
The phosphoinositide 3-kinase (PI3K)/mechanistic target of rapamycin (mTOR) pathway is frequently overactivated in cancer, and drives cell growth, proliferation, survival, and metastasis. Here, we report a structure-activity relationship study, which led to the discovery of a drug-like adenosine 5′-triphosphate-site PI3K/mTOR kinase inhibitor: (S)-4-(difluoromethyl)-5-(4-(3-methylmorpholino)-6-morpholino-1,3,5-triazin-2-yl)pyridin-2-amine (PQR530, compound 6), which qualifies as a clinical candidate due to its potency and specificity for PI3K and mTOR kinases, and its pharmacokinetic properties, including brain penetration. Compound 6 showed excellent selectivity over a wide panel of kinases and an excellent selectivity against unrelated receptor enzymes and ion channels. Moreover, compound 6 prevented cell growth in a cancer cell line panel. The preclinical in vivo characterization of compound 6 in an OVCAR-3 xenograft model demonstrated good oral bioavailability, excellent brain penetration, and efficacy. Initial toxicity studies in rats and dogs qualify 6 for further development as a therapeutic agent in oncology.
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
, (2018/11/23)
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.
