877-89-4Relevant academic research and scientific papers
NUCLEOPHILIC SUBSTITUTION REACTIONS OF 2,4,6-TRIS(TRINITROMETHYL)-1,3,5-TRIAZINE. 1. INTERACTION OF 2,4,6-TRIS(TRINITROMETHYL)-1,3,5-TRIAZINE WITH ALCOHOLS, DIOLS, AMMONIA AND SECONDARY AMINES
Shastin, A. V.,Godovikova, T. I.,Golova, S. P.,Khmel'nitskii, L. I.,Korsunskii, B. L.
, p. 596 - 600 (1995)
A study has been made of nucleophilic substitution reactions of 2,4,6-tris(trinitromethyl)-1,3,5-triazine with certain nucleophiles.The possibility of replacing one, two, or three trinitromethyl groups in this compound has been demonstrated.
A uniquely fabricated Cu(II)-metallacycle as a reusable highly sensitive dual-channel and practically functional metalloreceptor for Fe3+ and Ca2+ ions: An inorganic site of cation detection
Thakur, Neha,Pandey, Mrituanjay D.,Pandey, Rampal
, p. 3582 - 3592 (2018)
The present study deals with the formation of cyanuric chloride·1,2-di(pyridin-2-yl)disulfane 1 co-crystal and trimethylcyanuric acid 2 through unusual reactions of cyanuric chloride (CC). Reaction of co-crystal 1 with Co(ii) and Cu(ii) led to the formation of di(pyridin-2-yl)sulfane 1′ through a desulfurization reaction and complexes [Co(1′)Cl2] (3) and [Cu(1′)2-(μ2-SO4)2(H2O)2] (4). The structures of 1-4 were verified using X-ray single crystal analysis. The Cu(ii)-metallacycle 4 acts as a dual-channel metalloreceptor for Fe3+ and Ca2+ through a fluorescence 'turn-on' response for Ca2+, a 'turn-off' response for Fe3+, and changes in cyclic voltammograms in pure aqueous-buffer medium (1.0 M Tris-HCl, pH 7.4). The limits of detection (LOD) for Fe3+ and Ca2+ were estimated to be 30 ppb and 0.2 ppm, respectively. For the first time, the EPR technique was applied to detect a paramagnetic ion (Fe3+) using a paramagnetic probe (4), which exhibited considerable change upon interaction with Fe3+. Further, structural elucidation of 4, use of Co(ii)-complex 3 as a model compound, and FTIR and mass spectral studies suggested that the detection of cations by Cu(ii)-metallacycle 4 occurs through its unique inorganic detection site (six oxygen atoms from sulphate and water groups). Due to its higher selectivity of Fe3+ over Ca2+ and other metal ions as well as its LOD for Fe3+, which is lower than the US Environmental Protection Agency permitted maximum level in drinking water (5.4 μmol L-1), 4 was successfully used for practical detection of Fe3+ in environmental water samples. The exceptionality of this report comprises the detection of vital cations using a binuclear Cu(ii) metallacycle probe, utilizing the EPR technique, binding through an inorganic site and the practical application of 4 toward Fe3+ sensing.
Targeting the erythrocytic and liver stages of malaria parasites with s-triazine-based hybrids
Rodrigues, Catarina A. B.,Frade, Raquel F. M.,Albuquerque, Inês S.,Perry, Maria J.,Gut, Jiri,Machado, Marta,Rosenthal, Philip J.,Prudêncio, Miguel,Afonso, Carlos A. M.,Moreira, Rui
, p. 883 - 890 (2015/05/05)
A diversity-oriented library of s-triazine-based hybrids was screened for activity against the chloroquine-resistant Plasmodium falciparum W2 strain. The most striking result was sub-micromolar activity against cultured erythrocytic-stage parasites of hybrid molecules containing one or two 8-aminoquinoline moieties. These compounds were not clearly toxic to human cells. The most effective blood-schizontocidal s-triazine derivatives were then screened for activity against the liver stage of malaria parasites. The s-triazine hybrid containing two 8-aminoquinoline moieties and one chlorine atom emerged as the most potent against P. berghei liver-stage infection, active in the low nanomolar region, combined with good metabolic stability in rat liver microsomes. These results indicate that s-triazine-8-aminoquinoline-based hybrids are excellent starting points for lead optimization as dual-stage antimalarials.
USE OF A L,3J5-TRIAZIN-2-YL PHOSPHORAMIDATE COMPOUND IN THE SYNTHESIS OF SOFOSBUVIR
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Page/Page column 12, (2015/11/09)
The present invention relates to a new type of 1,3.5-triazin-2-yl phosphoramidates of general formula I with the absolute configuration (S) at the phosphorus atom, an Sp diastereoisomer, wherein R1 and R2 can independently be H, a C1-C6 (un)branched alkyl, a C1-C6 (un)branched alkoxy group, a C1-C6 (un)branched alkylsulfanyl group, C1-C6 (un)branched monoalkylamino or dialkylamino group, including cyclic amino groups, e.g. pyrrolidino, piperidino or morpholino group; and to their use for the production of biologically active phosphoramidate prodrugs, especially sofosbuvir of formula II. Sofosbuvir II is a nucleotide inhibitor of the RNA polymerase, used for the treatment of hepatitis C in the form of a prodrug, releasing the active antiviral agent 2'-deoxy-2'-a-fluoro- P-C-methyluridine-5'-triphosphate in the organism.
Study of the Reactivities of Acid-Catalyzed O-Benzylating Reagents Based on Structural Isomers of 1,3,5-Triazine
Fujita, Hikaru,Hayakawa, Naoko,Kunishima, Munetaka
, p. 11200 - 11205 (2015/11/18)
We have demonstrated O-benzylating abilities of both 4,6-bis(benzyloxy)-1,3,5-triazin-2(1H)-one (DiBOT) and 6-(benzyloxy)-1,3,5-triazine-2,4(1H,3H)-dione (MonoBOT), which have been previously suggested as reaction intermediates of the acid-catalyzed benzylation of 2,4,6-tris(benzyloxy)-1,3,5-triazine (TriBOT). We studied the effect on the reactivity of acid-catalyzed O-benzylation caused by the isomeric core triazine structures in these compounds by carrying out a kinetic study and estimating relative basicities using model compounds. Since MonoBOT showed superior reactivity, 1,3,5-triazine-2,4(1H,3H)-dione is a promising core structure for acid-catalyzed alkylating reagents.
Formation of a new 1D coordination polymer by in situ ligand reaction of 2,4,6-tris(pyrazol-1-yl)-1,3,5-s-triazine
Cao, Qiang
, p. 648 - 651 (2013/02/25)
Solvothermal reactions of Zn(NO3)2·6H2O, 1,4-benzenedicarboxylic acid (H2BDC) and 2,4,6-tris(pyrazol-1-yl)-1, 3,5- s-triazine, yielded a new coordination polymer [Zn(BDC)(pz) ·H 2O]n (pz= pyrazole). The in situ methanolysis reaction of 2,4,6-tris(pyrazol-1-yl)-1,3,5-s-triazine with pyrazole and 2,4,6-trismethoxy-1, 3,5-triazine was confirmed by their single-crystal structures. [Zn(BDC)(pz)·H2O]n was characterised by elemental analysis, IR, powder X-ray diffraction, photoluminescence and thermogravimetric analyses.
Synthesis and functionalization of heteroatom-bridged bicyclocalixaromatics, large molecular triangular prisms with electron-rich and -deficient aromatic interiors
Naseer, Muhammad Moazzam,Wang, De-Xian,Zhao, Liang,Huang, Zhi-Tang,Wang, Mei-Xiang
body text, p. 1804 - 1813 (2011/06/10)
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.
Anion-induced assembly of five-coordinated mercury(II) complexes and density functional theory calculations to study bond dissociation energies of long Hg-N bonds
Zhou, Hong-Ping,Gan, Xiao-Ping,Li, Xian-Lei,Liu, Zhao-Di,Geng, Wen-Qian,Zhou, Fei-Xia,Ke, Wei-Zai,Wang, Peng,Kong, Lin,Hao, Fu-Ying,Wu, Jie-Ying,Tian, Yu-Peng
body text, p. 1767 - 1776 (2011/11/29)
A series of new five-coordinated mercury(II) coordination complexes (Hg(TpzT)(SCN)2H2O (1), Hg(TpzT)I2H 2O (2), Hg(TpzT)Br2H2O (3), 2Hg(TpzT)Cl 2HgCl22H2O (4)) have been synthesized by self-assembling the flexible ligand 2,4,6-tri(pyrazole-1-yl)-1,3,5-triazine (TpzT) with HgX2 (X = SCN, I, Br, Cl). Various weak interactions including hydrogen bonds (O'HX, C'HX), p'p interactions, and SS contacts play significant roles in the final topological structures of the four compounds. Unexpectedly, 5 and 6 were obtained accidentally by self-assembling TpzT with MX2 (Zn(NO3)26H2O or CdI 2) in methanol and were assessed by X-ray crystallography, which indicated that there are nucleophilic substitution reactions. Surprisingly, all the Hg'N bonds of approximately 2.70 in length formed by the tridentate ligand and mercuric salt are rather unusual. So density functional theory (DFT) calculations (Amsterdam density functional, ADF) were employed to study the bond dissociation energies (BDE) of Hg'N bonds in 1'4 to assess the nature of the bonds. The calculation reveals the strong coordination nature of Hg'N bonds in 1'4 compared to that of the same coordination mode of compound A ((4′-(4-[4-(imidazole)phenylethylene]phenyl)-2,2′:6′, 2″-terpyridine)HgBr2CHCl3) with the normal range Hg'N bond lengths. And a similar trend is that the larger the anion and BDE become, the steadier the coordination complexes are.
A Simple Practical Method for the Synthesis of 4,6-Dimethoxy-1,3,5-triazin- 2(1H)-one Using Dimethylamine-Functionalized Solid-Phase Reagents
Hioki, Kazuhito,Ohshima, Keiichi,Sota, Yuko,Tanaka, Miki,Kunishima, Munetaka
body text, p. 542 - 544 (2009/07/25)
A simple practical method for the synthesis of 4,6-dimethoxy-1,3,5-triazin- 2(1H)-one was developed. The desired product was easily obtained from 2-chloro-4,6-dimethoxy-1,3,5-tri-azine and acetic acid by shaking with dimethylamine-functionalized silica ge
Reactions of hydrated electrons with triazine derivatives in aqueous medium
Varghese, Rani,Mohan, Hari,Manoj,Manoj,Aravind, Usha K.,Vandana,Aravindakumar
, p. 8171 - 8176 (2007/10/03)
A study is made of the kinetics and mechanism of the reaction of radiolytically produced hydrated electron (e-aq) with some triazine derivatives [1,3,5-triazine (T), 2,4,6-trimethoxy-1,3,5-triazine (TMT), 2,4-dioxohexahydro-1,3,5-triazine (DHT), 6-chloro N-ethyl N-(1-methylethyl)-1,3,5-triazine 2,4-diamine (atrazine, AT), and cyanuric acid (CA)] in aqueous medium using pulse and steady-state radiolysis techniques. The second-order rate constants were determined from the pseudo first-order decay of e-aq in the presence of triazines at 720 nm, and the values obtained with T, TMT, AT, and CA are in the order of 109 dm3 mol-1 s-1 and that of DHT was 10 8 dm3 mol-1 s-1 at pH 6. The transient absorption spectra from the reaction of e-aq with T and TMT are characterized by their λmax at 310 nm, and those of DHT and CA are around 280 and 290 nm, respectively. However, a very weak and featureless absorption spectrum is obtained from AT. On the basis of the spectral evidence and on the quantitative electron transfer from the transient intermediates to the oxidant, methyl viologen (MV2+), the intermediate radicals are assigned to N-protonated electron adducts (with the unpaired spin density at carbon) of triazines. The degradation profiles, monitored as the disappearance of parent triazine concentrations as a function of dose, obtained with AT, TMT, CA, and DHT, highlight the potential use of e-aq in the degradation of triazines.
