3140-74-7Relevant articles and documents
Discovery of ortho-carborane-conjugated triazines as selective topoisomerase I/II inhibitors
Nakamura, Hiroyuki,Shoji, Atsushi,Takeuchi, Ayano,Ban, Hyun Seung,Lee, Jong-Dae,Yamori, Takao,Kang, Sang Ook
, p. 1430 - 1437 (2011)
The cell growth inhibition profile of 2,4-(2-methyl-ortho-carboranyl)-4- (dimethylamino)-1,3,5-triazine (TAZ-6) was found to be similar to that of ICRF-193, a topoisomerase II inhibitor, as revealed by COMPARE analysis (correlation coefficient (r)≤0.724). Various mono-and di-ortho-carborane- substituted 1,3,5-triazines were synthesized based on the structure of TAZ-6 and tested for their ability to inhibit cell growth and the activities of topoisomerases I and II. Among the compounds synthesized, 3c, 4c, and 4f completely inhibited topoisomerase I activity without affecting topoisomerase II activity, whereas 3a and 3d completely inhibited topoisomerase II activity without affecting topoisomerase I activity, at 100μM.
Design and synthesis of a series of melamine-based nitroheterocycles with activity against trypanosomatid parasites
Baliani, Alessandro,Bueno, Gorka Jimenez,Stewart, Mhairi L.,Yardley, Vanessa,Brun, Reto,Barrett, Michael P.,Gilbert, Ian H.
, p. 5570 - 5579 (2005)
The parasites that give rise to human African trypanosomiasis (HAT) are auxotrophs for various nutrients from the human host, including purines. They have specialist nucleoside transporters to import these metabolites. In addition to uptake of purine nucleobases and purine nucleosides, one of these transporters, the P2 transporter, can carry melamine derivatives; these derivatives are not substrates for the corresponding mammalian transporters. In this paper, we report the coupling of the melamine moiety to selected nitro heterocycles with the aim of selectively delivering these compounds to the parasites. Some compounds prepared have similar in vitro trypanocidal activities as melarsoprol, the principal drug used against late-stage HAT, with 50% growth inhibitory concentrations in the submicromolar range. Selected compounds were also evaluated in vivo in rodent models infected with Trypanosoma brucei brucei and T. brucei rhodesiense and showed pronounced activity and in two cases were curative without overt signs of toxicity. Compounds were also tested against other trypanosomatid pathogens, Leishmania donovani and Trypanosoma cruzi, and significant activity in vitro was noted for T. cruzi against which various nitro heterocycles are already registered for use.
Design, synthesis, anticancer, antibacterial, and antifungal evaluation of 4-aminoquinoline-1,3,5-triazine derivatives
Bhat, Hans Raj,Ghosh, Surajit Kumar,Masih, Anup,Shakya, Anshul,Singh, Udaya Pratap
, (2019/12/27)
A series of 4-aminoquinoline 1,3,5-triazine derivatives were synthesized and evaluated for anticancer activity against cancer cell lines HeLa, MCF-7, HL-60, HepG2 where these derivatives exert significant anticancer activity. The molecules found nontoxic against MCF-12A. The molecules also showed potent inhibition of EGFR-TK as compared to eroltinib in enzyme-based assay. The newly synthesized derivatives were screened for their in vitro antibacterial and antifungal activity against Bacillus subtilis, Bacillus cereus, Staphylococcus aureus, Proteus vulgaris, Escherichia coli, Pseudomonas aeruginosa and Candida albicans, Aspergillus niger, Aspergillus fumigatus using cefixime and fluconazole as standard. Antibacterial screening results suggest that compound 7c showed potent activity against S. aureus, P. aeruginosa, and P. vulgaris. In antifungal screening, compound 7b showed significant activity against A. niger, A. fumigatus and moderate activity against C. albicans.
N-Methylmelamines: Synthesis, Characterization, and Physical Properties
List, Manuela,Puchinger, Helmut,Gabriel, Herbert,Monkowius, Uwe,Schwarzinger, Clemens
, p. 4066 - 4075 (2016/06/09)
N-Methylmelamines have recently gained importance as valuable compounds for manufacturing modified melamine formaldehyde resins and other polymer building blocks. A great advantage of these polymers is the reduction of the carcinogenic formaldehyde. Selecting the polymerization processes (e.g., substance polymerization, polymerization in solution) and controlling the polymerization reaction and properties of these novel materials requires knowledge of the properties of the individual melamine derivatives used as new building blocks. All possible permutations of N-methylmelamines were prepared, and reaction progress was monitored by GC/MS. 2,4,6-Tris(dimethylamino)-1,3,5-triazine was prepared to complete the series; this is, however, also a possible byproduct in various synthesis routes. The reaction conditions were optimized to obtain high yields of each derivative with the highest possible purity. The substances were characterized by NMR and IR spectroscopy, mass spectrometry, elemental analysis, and single-crystal X-ray diffraction. In addition, physical properties, such as solubility, melting points, and pKb values, were determined. The number of amino-, methylamino-, and dimethylamino groups has a significant effect on these properties. In summary, we found that by increasing the number of amino- and methylamino groups, solubility and pKb increase. With increasing number of amino groups, the compounds tend to form hydrogen bonds, and thus, the melting point shifts to higher temperature ranges where they start to decompose.
