61-82-5Relevant articles and documents
A 3D chiral metal-organic framework based on left-handed helices containing 3-amino-1 H-1,2,4-triazole ligand
Liu, Bing,Yang, Tian-Yi,Feng, Hui-Jun,Zhang, Zong-Hui,Xu, Ling
, p. 90 - 94 (2015)
A chiral metal-organic framework, [Cu(atr)(OH)]0.5H2O0.5en (1) (Hatr=3-amino-1 H-1,2,4-triazole, en=ethylenediamine), was constructed via diffusion reaction of the achiral Hatr ligand and CuSO4 as starting materials. Compound 1 crystallizes in the chiral space group P3221 and features a porous metal-organic framework with 44.1% solvent-accessible volume fabricated by left-handed helices with a pitch height of lp=10.442 ?. Six helices gather around in a cycle forming a large honeycomb channel with a 6.58 ? inner diameter. Cu(II) center and atr- ligand regarded as 3-connected nodes, compound 1 can be simplified to a 3-c uninodal {4.122} (qtz-h) topological network. A gradual decreasing in the magnetic moment depending on temperature decreasing indicates an antiferromagnetic interaction in 1. The powder XRD confirms the bulk sample is a single crystal pure phase, and the thermogravimetric analysis shows the thermal stability of 1 is up to ca. 240 °C.
Comparative study between the anti-P. falciparum activity of triazolopyrimidine, pyrazolopyrimidine and quinoline derivatives and the identification of new PfDHODH inhibitors
Silveira, Flávia F.,de Souza, Juliana O.,Hoelz, Lucas V.B.,Campos, Vinícius R.,Jabor, Valquíria A.P.,Aguiar, Anna C.C.,Nonato, M. Cristina,Albuquerque, Magaly G.,Guido, Rafael V.C.,Boechat, Nubia,Pinheiro, Luiz C.S.
, (2020/11/10)
In this work, we designed and synthesized 35 new triazolopyrimidine, pyrazolopyrimidine and quinoline derivatives as P. falciparum inhibitors (3D7 strain). Thirty compounds exhibited anti-P. falciparum activity, with IC50 values ranging from 0.030 to 9.1 μM. The [1,2,4]triazolo[1,5-a]pyrimidine derivatives were more potent than the pyrazolo[1,5-a]pyrimidine and quinoline analogues. Compounds 20, 21, 23 and 24 were the most potent inhibitors, with IC50 values in the range of 0.030–0.086 μM and were equipotent to chloroquine. In addition, the compounds were selective, showing no cytotoxic activity against the human hepatoma cell line HepG2. All [1,2,4]triazolo[1,5-a]pyrimidine derivatives inhibited PfDHODH activity in the low micromolar to low nanomolar range (IC50 values of 0.08–1.3 μM) and did not show significant inhibition against the HsDHODH homologue (0–30% at 50 μM). Molecular docking studies indicated the binding mode of [1,2,4]triazolo[1,5-a]pyrimidine derivatives to PfDHODH, and the highest interaction affinities for the PfDHODH enzyme were in agreement with the in vitro experimental evaluation. Thus, the most active compounds against P. falciparum parasites 20 (R = CF3, R1 = F; IC50 = 0.086 μM), 21 (R = CF3; R1 = CH3; IC50 = 0.032 μM), 23, (R = CF3, R1 = CF3; IC50 = 0.030 μM) and 24 (R = CF3, 2-naphthyl; IC50 = 0.050 μM) and the most active inhibitor against PfDHODH 19 (R = CF3, R1 = Cl; IC50 = 0.08 μM - PfDHODH) stood out as new lead compounds for antimalarial drug discovery. Their potent in vitro activity against P. falciparum and the selective inhibition of the PfDHODH enzyme strongly suggest that this is the mechanism of action underlying this series of new [1,2,4]triazolo[1,5-a]pyrimidine derivatives.
Synthesis of a novel functionalized tricyclic pyrimidine-fused 1,5-benzodiazepine library
Qomi, Hamid Reza,Habibi, Azizollah
, p. 2991 - 3001 (2017/04/28)
A series of novel tricyclic pyrimidine-fused 1,5-benzodiazepines (PFBZDs) was synthesized using an enaminone-based approach. The key step in the synthetic strategy involves the formation of the C[dbnd]C[sbnd]NMe2 structure on vicinal carbonyl groups of the 1H-1,5-benzodiazepine-2,4(3H,5H)-dione (BZD). The synthesis of pyrimidine-fused 1,5-benzodiazepines was performed by a simple and efficient method in good to excellent yields under mild and green conditions. The β-enaminoamide intermediates were condensed with thiourea and guanidine derivatives to form the corresponding tricyclic PFBZDs. But reaction of aminoguanidine, thiosemicarbazide, 4-phenylthiosemicarbazide and ethane-1,2-diamine with β-enaminoamides didn't produce any desired product and led to recovery of the corresponding starting BZD.
Synthesis and antimicrobial evaluation of aminoguanidine and 3-amino-1,2,4-triazole derivatives as potential antibacterial agents
Zhang, Tian-Yi,Li, Chao,Li, Ya-Ru,Li, Xiao-Zhen,Sun, Liang-Peng,Zheng, Chang-Ji,Piao, Hu-Ri
, p. 1063 - 1075 (2016/11/25)
A series of aminoguanidine derivatives bearing a 1,3,4-oxadiazole or piperazine moiety has been synthesized and fully characterized together with a series of 3-amino-1,2,4-triazole derivatives, and the resulting compounds were evaluated for their antibacterial activity. Most of these compounds showed broad-spectrum antibacterial activities against both Gram-positive and Gramnegative bacteria with minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) values in the range of 1-64 μg/mL, including multidrug-resistant clinical isolates and a fungus. Notably, compounds 19e and 19f exhibited higher levels of activity than gatifloxacin and moxifloxacin against several methicillin-resistant Staphylococcus aureus (3167 and 3506) and quinolone-resistant S. aureus (3505 and 3519) strains with MIC and MBC values in the range of 1-2 μg/mL. These two compounds also displayed significant antifungal activity against Candida albicans 7535 with MIC value of 1 μg/mL, which were equivalent to MIC value of standard drug fluconazole. These results therefore indicate that aminoguanidine derivatives that do not contain a piperazine moiety are interesting scaffolds for the development of novel antibacterial agents.
Kinetics and mechanism of uncatalyzed and ruthenium(III)-catalyzed oxidation of formamidine derivative by hexacyanoferrate(III) in aqueous alkaline medium
FAWZY
, p. 733 - 743 (2016/05/19)
The catalytic effect of ruthenium(III) on the oxidation of N, N-dimethyl- N′-(4H-1,2,4-triazol- 3-yl) formamidine (ATF) by hexacyanoferrate(III) (HCF) was studied spectrophotometrically in aqueous alkaline medium. Both uncatalyzed and catalyzed reactions showed first order kinetics with respect to [HCF], whereas the reaction orders with respect to [ATF] and [OH ?] were apparently less than unity over the concentration range studied. A first order dependence with respect to [RuIII] was obtained. Increasing ionic strength increased the rate of uncatalyzed reaction and decreased the rate of the catalyzed one Plausible mechanistic schemes of oxidation reactions have been proposed. In both cases, the final oxidation products are identified as aminotriazole, dimethyl amine and carbon dioxide. The rate laws associated with the reaction mechanisms are derived. The reaction constants involved in the different steps of the mechanisms were calculated. The activation and thermodynamic parameters have been computed and discussed. [Figure not available: see fulltext.]
Kinetic and Mechanistic Aspects of Oxidation of Aminotriazole Formamidine by Cerium(IV) in Aqueous Perchloric and Sulfuric Acid Solutions: A Comparative Study
Fawzy, Ahmed
, p. 246 - 264 (2016/02/23)
The kinetics of the oxidation of an aminotriazole formamidine derivative, N,N-dimethyl-N′-(4H-1,2,4-triazol-3-yl) formamidine (ATF) by cerium(IV) has been studied spectrophotometrically in aqueous perchloric and sulfuric acid solutions at constant ionic strength of 1.0 mol·dm-3. In both acids, the reaction shows first order kinetics with respect to [Ce(IV)], whereas the orders with respect to [ATF] are less than unity. The reaction exhibits negative fractional order kinetics with respect to [H+]. The rates of reaction are not significantly affected by variations of either ionic strength or relative permittivity of the reaction's media. Addition of cerium(III) product does not affect the rates. Plausible mechanistic schemes for the reactions have been proposed. In both cases, the final oxidation products were identified as aminotriazole, dimethyl amine and carbon dioxide. Under comparable experimental conditions, the oxidation rate in perchloric acid solution is about sixfold higher than that in sulfuric acid solution. The effect of temperature on the rates has also been studied and activation parameters have been evaluated and discussed. The rate laws associated with the reaction mechanisms are derived.
Design and synthesis of new N-(5-Trifluoromethyl)-1H-1,2,4-triazol-3-yl benzenesulfonamides as possible antimalarial prototypes
Boechat, Nubia,Pinheiro, Luiz C.S.,Santos-Filho, Osvaldo A.,Silva, Isabor C.
experimental part, p. 8083 - 8097 (2011/10/31)
A rational approach was used to synthesize a new set of 15 1H-1,2,4-triazol-3-yl benzenesulfonamide derivatives with the aim of developing new antimalarial lead compounds. These derivatives were prepared in yields between 50% and 62%, and their structures were elucidated using IR, 1H-, 13C-, 19F-NMR, MS and elemental analysis. A docking study based on sulfonamides previously used against malaria identified trifluoromethyl-substituted derivatives to be the best lead compounds for new antimalarial drug development.
Synthesis of N4-amino and N4-hydroxy derivatives of 5-azacytidine. A facile rearrangement of the N4-amino derivative to 5-(3-β-D-ribofuranosylureido)-1H-1,2,4-triazole
Piskala, Alois,Hanna, Naeem B.,Masojidkova, Milena,Fiedler, Pavel,Votruba, Ivan
, p. 905 - 917 (2007/10/03)
Treatment of methoxyribosyltriazinone 4 with hydrazine in methanol afforded crude 4-hydrazino-1-β-D-ribofuranosyl-1,3,5-triazin-2(1H)-one (N 4-amino-5-azacytidine) (2), which rearranged rapidly to isomeric 5-ribosylureidotriazole 6. The rearrangement proceeds easily also in water solutions of 2. Alkaline hydrolysis of 6 gave a mixture of 5-ureidotriazole 7 and 5-aminotriazole 8. Acid hydrolysis of 6 afforded only 7. This compound was also prepared by thermal rearrangement of 5-amino-1-carbamoyltriazole 9 or on reaction of cyano(formyl)guanidine 10 with hydrazine hydrochloride. Treatment of benzoylated methoxyribosyltriazinone 4a with hydrazine in methanol gave only the rearranged product 6a. Reaction of tribenzoylribosyl isocyanate 12 with aminotriazole 8 gave 1-triazolecarboxamidotribenzoylribose 13, which afforded by methanolysis oxazoloribofuranose 14 and aminotriazole 8. Compound 14 was also obtained by methanolysis of blocked ribosylcarbamate 16. Reaction of methoxyribosyltriazinone 4 with hydroxylamine in methanol afforded 4-hydroxylamino-1-β-D-ribofuranosyl-1,3,5-triazin-2(1H)-one (N 4-hydroxy-5-azacytidine) (3), which on the action of excess hydroxylamine yielded 1-cyano-1-hydroxy-5-β-D-ribofuranosylisobiuret (19). Treatment of methoxy-1,3,5-triazinone 18 with a solution of hydroxylamine in methanol gave 4-hydroxylamino-1-methyl-1,3,5-triazin-2(1H)-one (N 4-hydroxy1-methyl-5-azacytosine) (17). Heating of cyano(formyl)guanidine 10 with hydroxylamine hydrochloride in water lead to the formation of triuret (21). The mechanisms of the reactions of methoxyribosyltriazinone 4 with hydrazine and hydroxylamine are discussed. Compounds 2, 6 and 19 exhibited no significant antibacterial or cytostatic activity.
Acylation of amino-1,2,4-triazoles
Barmin,Kartavykh,Korolev,Tugai,Grebenkin,Mel'nikov
, p. 557 - 566 (2007/10/03)
A scheme of acylation of amino-1,2,4-triazoles under conditions of low-temperature polycondensation is proposed. The effect of reaction conditions on the yield and properties of reaction products is established.
Synthesis of 1,3-bis(1,2,4-triazol-3-amino)-2,4,6-trinitrobenzene and its thermal and explosive behaviour
Agrawal,Mehilal,Prasad,Surve
, p. 583 - 585 (2007/10/03)
1,3-Bis(1,2,4-triazol-3-amino)-2,4,6-trinitrobenzene (BTATNB) has been synthesized by condensing 1,3-dichloro-2,4, 6-trinitrobenzene and 3-amino-1,2,4-triazole in dimethyl formamide (DMF) at 125 ± 2 °C. The product has been characterized by elemental analysis, Fourier transform infrared (FTIR), nuclear magnetic resonance (NMR) and mass spectrometry. The data on thermal and explosive properties indicate that BTATNB is slightly more thermally stable than 3-picrylamino-1,2,4-triazole (PATO). At the same time, it is safer towards impact and friction.
