4967-77-5Relevant academic research and scientific papers
One-pot microwave-assisted solvent free synthesis of simple alkyl 1,2,3-triazole-4-carboxylates by using trimethylsilyl azide
Taherpour, Avat Arman,Kheradmand, Khojasteh
, p. 131 - 133 (2009)
A fast one-pot microwave-assisted solvent free synthesis of simple alkyl 1,2,3-triazole-4-carboxylate derivatives by 1,3-dipolar cycloaddition reactions with trimethylsilyl azide (Me3Si-N3) on the alkylpropiolates and DMAD in high yi
MeOPEG-bounded azide cycloadditions to alkynyl dipolarophiles
Garanti, Luisa,Molteni, Giorgio
, p. 1133 - 1135 (2003)
The MeOPEG-supported azide 2 was reacted in the presence of a number of alkynyl dipolarophiles. The corresponding 1-MeOPEG-supported-1,2,3-triazoles were obtained in nearly quantitative yields. Acidic hydrolysis of the cycloadducts 5b and 6b caused the removal of the MeOPEG pendant giving 4-methoxycarbonyl-1,2,3-triazole 9 and 5-methoxycarbonyl-1,2,3-triazole 10, respectively.
The synthesis of methyl triazole-4-carboxylate gold(I) complex and application on allene synthesis and alkyne hydration
Hu, Wenkang,Shan, Liang,Ma, Fudong,Zhang, Yilin,Yang, Yongchun,Wang, Dawei
, (2019/10/14)
The methyl 1H-1,2,3-triazole-4-carboxylate containing a strong electron-withdrawing group was developed and applied as a ligand for gold(I) cations. The resulting ester-triazole gold(I) complex was investigated for its efficiency in catalyzing allene synthesis and alkyne hydration, in which an excellent catalytic efficiency was observed with low catalyst loadings.
Structure Kinetics Relationships and Molecular Dynamics Show Crucial Role for Heterocycle Leaving Group in Irreversible Diacylglycerol Lipase Inhibitors
Janssen, Antonius P.A.,Van Hengst, Jacob M.A.,Béquignon, Olivier J.M.,Deng, Hui,Van Westen, Gerard J.P.,Van Der Stelt, Mario
, p. 7910 - 7922 (2019/10/11)
Drug discovery programs of covalent irreversible, mechanism-based enzyme inhibitors often focus on optimization of potency as determined by IC50-values in biochemical assays. These assays do not allow the characterization of the binding activity (Ki) and reactivity (kinact) as individual kinetic parameters of the covalent inhibitors. Here, we report the development of a kinetic substrate assay to study the influence of the acidity (pKa) of heterocyclic leaving group of triazole urea derivatives as diacylglycerol lipase (DAGL)-α inhibitors. Surprisingly, we found that the reactivity of the inhibitors did not correlate with the pKa of the leaving group, whereas the position of the nitrogen atoms in the heterocyclic core determined to a large extent the binding activity of the inhibitor. This finding was confirmed and clarified by molecular dynamics simulations on the covalently bound Michaelis-Menten complex. A deeper understanding of the binding properties of covalent serine hydrolase inhibitors is expected to aid in the discovery and development of more selective covalent inhibitors.
Design, synthesis, and antiviral activity of new 1H-1,2,3-triazole nucleoside ribavirin analogs
De Lourdes G. Ferreira, Maria,Pinheiro, Luiz C. S.,Santos-Filho, Osvaldo A.,Pecanha, Marta D. S.,Sacramento, Carolina Q.,Machado, Viviane,Ferreira, Vitor F.,Souza, Thiago Moreno L.,Boechat, Nubia
, p. 1501 - 1511 (2014/03/21)
Ribavirin is a broad antiviral compound with demonstrated activity against herpes simplex virus (HSV), human immunodeficiency virus HIV-1, influenza virus, respiratory syncytial virus, and hepatitis C virus, among other viruses. However, routine clinical use of ribavirin is limited because this compound is considerably cytotoxic. Herein, we describe the design, synthesis, and antiviral activity of new nucleoside ribavirin analogs based on the following: (1) ring bioisosterism of a 1,2,4-triazole for a 1,2,3-triazole; (2) amide group exchange for other substituents, such as c-propyl, methyl carboxylate, or trifluoromethyl groups; and (3) the ribofuranose remained linked to the triazole ring. Compounds 5a-c were obtained with yields of 65-36 % and tested against Influenza A and HSV-1 replication as well as reverse transcriptase (RT) from human immunodeficiency virus type 1 (HIV-1 RT). Compound 5b (R = CO 2CH3) was the most effective analog, with IC50 values 14 and 3.8 μM for Influenza A and HIV-1 RT, respectively.
Debenzylation of functionalized 4- and 5-substituted 1,2,3-triazoles
Farooq, Tahir,Sydnes, Leiv K.,Toernroos, Karl W.,Haug, Bengterik
experimental part, p. 2070 - 2078 (2012/08/07)
A range of 4- and 5-substituted N-benzyl-1,2,3-triazoles have been submitted to debenzylation using Pd/C and hydrogen in the presence of 1,1,2-trichloroethane. Triazoles with oxygen-containing substituents are efficiently debenzylated under these conditio
ZnO nanoparticles-mediated regioselective synthesis of methyl-iV-alkylated 1,2,3-triazole-4-carboxylates
Prabakaran,Khan, Fazlur-Rahman Nawaz,Jin, Jong Sung
experimental part, p. 1101 - 1109 (2012/08/28)
The 1,2,3-triazoles are versatile synthetic intermediates of many biologically active compounds, and their N-1 substituted analogues are potential pharmaceutically important derivatives. In this study, an efficient regioselective N-alkylation reaction of
Novel synthetic approaches to (Trifluoromethyl)triazoles
Sibgatulin, Dmytriy A.,Bezdudny, Andrii V.,Mykhailiuk, Pavel K.,Voievoda, Nataliia M.,Kondratov, Ivan S.,Volochnyuk, Dmitry M.,Tolmachev, Andrey A.
experimental part, p. 1075 - 1077 (2010/05/18)
New synthetic procedures for the trifluoromethyl-substituted triazoles, 3-(trifluoromethyl)-4H-1,2,4-triazole and 4-(trifluoromethyl)-1H-1,2,3-triazole, have been elaborated. The target compounds were prepared from commercially available trifluoroacethydr
1,3-Dipolar cycloadditions of MeOPEG-bounded azides
Molteni, Giorgio,Del Buttero, Paola
, p. 4983 - 4987 (2007/10/03)
1,3-Dipolar cycloadditions of MeOPEG-supported azide 2 with a variety of dipolarophiles have been studied. 1-MeOPEG-supported 1,2,3-triazoles 4 and 5, 1,2,3,4-tetrazoles 12 and aziridine 14 were obtained in nearly quantitative yields. The removal of the MeOPEG moiety from the 1,2,3-triazole nucleus was achieved by acidic cleavage of the cycloadduct mixtures 4 and 5 giving 4- and 5-substituted-1,2,3-triazoles 6 and 7.
Selective, Orally Active γ-Aminobutyric AcidA α5 Receptor Inverse Agonists as Cognition Enhancers
Sternfeld, Francine,Carling, Robert W.,Jelley, Richard A.,Ladduwahetty, Tamara,Merchant, Kevin J.,Moore, Kevin W.,Reeve, Austin J.,Street, Leslie J.,O'Connor, Desmond,Sohal, Bindi,Atack, John R.,Cook, Susan,Seabrook, Guy,Wafford, Keith,Tattersall, F. David,Collinson, Neil,Dawson, Gerard R.,Castro, José L.,MacLeod, Angus M.
, p. 2176 - 2179 (2007/10/03)
Nonselective inverse agonists at the γ-aminobutyric acidA (GABA-A) benzodiazepine binding site have cognition-enhancing effects in animals but are anxiogenic and can precipitate convulsions. Herein, we describe novel GABA-A α5 subtype inverse agonists leading to the identification of 16 as an orally active, functionally selective compound that enhances cognition in animals without anxiogenic or convulsant effects. Compounds of this type may be useful in the symptomatic treatment of memory impairment associated with Alzheimer's disease and related dementias.
