4461-15-8Relevant academic research and scientific papers
An efficient and convenient protocol for the synthesis of optically active [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole derivatives containing L-amino acid moieties
Foroughifar, Naesr,Ebrahimi, Sattar,Mobinikhaledi, Akbar,Mozafari, Reza
, p. 211 - 214 (2011)
New triazolothiadiazoles bearing L-amino acid moieties were synthesized by reaction of 4-amino-5-phenoxy-4 H-1,2,4-triazole-3-thiol with l-amino acids in the presence of phosphorus oxychloride. 2011 · Copyright by Walter de Gruyter.
1,2,4-Triazole-3-thione Compounds as Inhibitors of Dizinc Metallo-β-lactamases
Sevaille, Laurent,Gavara, Laurent,Bebrone, Carine,De Luca, Filomena,Nauton, Lionel,Achard, Maud,Mercuri, Paola,Tanfoni, Silvia,Borgianni, Luisa,Guyon, Carole,Lonjon, Pauline,Turan-Zitouni, Gülhan,Dzieciolowski, Julia,Becker, Katja,Bénard, Lionel,Condon, Ciaran,Maillard, Ludovic,Martinez, Jean,Frère, Jean-Marie,Dideberg, Otto,Galleni, Moreno,Docquier, Jean-Denis,Hernandez, Jean-Fran?ois
, p. 972 - 985 (2017/06/27)
Metallo-β-lactamases (MBLs) cause resistance of Gram-negative bacteria to β-lactam antibiotics and are of serious concern, because they can inactivate the last-resort carbapenems and because MBL inhibitors of clinical value are still lacking. We previously identified the original binding mode of 4-amino-2,4-dihydro-5-(2-methylphenyl)-3H-1,2,4-triazole-3-thione (compound IIIA) within the dizinc active site of the L1 MBL. Herein we present the crystallographic structure of a complex of L1 with the corresponding non-amino compound IIIB (1,2-dihydro-5-(2-methylphenyl)-3H-1,2,4-triazole-3-thione). Unexpectedly, the binding mode of IIIB was similar but reverse to that of IIIA. The 3 D structures suggested that the triazole–thione scaffold was suitable to bind to the catalytic site of dizinc metalloenzymes. On the basis of these results, we synthesized 54 analogues of IIIA or IIIB. Nineteen showed IC50 values in the micromolar range toward at least one of five representative MBLs (i.e., L1, VIM-4, VIM-2, NDM-1, and IMP-1). Five of these exhibited a significant inhibition of at least four enzymes, including NDM-1, VIM-2, and IMP-1. Active compounds mainly featured either halogen or bulky bicyclic aryl substituents. Finally, some compounds were also tested on several microbial dinuclear zinc-dependent hydrolases belonging to the MBL-fold superfamily (i.e., endonucleases and glyoxalase II) to explore their activity toward structurally similar but functionally distinct enzymes. Whereas the bacterial tRNases were not inhibited, the best IC50 values toward plasmodial glyoxalase II were in the 10 μm range.
An efficient and convenient protocol for the synthesis of optically active 1,2,4-triazolo-[3,4-b]-[1,3,4]-thiadiazole, 1,3,4-oxadiazole and 1,3,4-thiadiazole derivatives having L-amino acid moieties
Foroughifara, Naser,Ebrahimib, Sattar,Mobinikhaldeic, Akbar,Mozafaric, Reza
body text, p. 1 - 4 (2012/05/05)
Aseries of novel bis triazolothiadiazole, 1,3,4-oxadiazole and 1,3,4-thiadiazole derivatives attached to L-amino acid moieties were synthesized in good yields using a simple and practical method. The structure of all synthesized compounds was confirmed by IR, 1H NMR, 13C NMR spectroscopy and elemental analysis.
Studies on fused heterocyclic 3,6-disubstituted-1,2, 4-triazolo-1,3,4- thiadiazoles: Synthesis and biological evaluation
Husain, Asif,Naseer, Md. Arif
, p. 47 - 54 (2012/02/04)
In this study, a series of 3,6-disubstituted-1,2, 4-triazolo-[3,4-b]-1,3,4- thiadiazoles (5a-t) were synthesized by condensing 4-amino-3-mercapto-(4H)-1,2, 4-triazoles (4a-c) with different aromatic or aroyl acids through one-pot reaction. The compounds were evaluated for their anti-inflammatory, analgesic, ulcerogenic, and lipid peroxidation actions. Some of the newly synthesized compounds showed very good anti-inflammatory activity with low GI toxicity and reduced lipid peroxidation. These compounds also showed interesting profile of analgesic activity in acetic acid-induced writhing test. The findings of the study indicate that the synthesized compounds have superior GI safety profile along with reduction in lipid peroxidation as compared to that of the standard. Springer Science+Business Media, LLC 2010.
Synthesis of Some Substituted 4-(5-Nitro-2-furfurylideneamino)-5-mercapto-1,2,4-triazoles and 7H-6-(5-Nitro-2-furyl)-s-triazolothiadiazines
Holla, B. Shivarama,Kalluraya, Balakrishna
, p. 683 - 685 (2007/10/02)
Seven 4-amino-3-aryloxymethyl-5-mercapto-1,2,4-triazoles (1a-g) have been synthesized and converted into 3-aryloxymethyl-4-(5-nitro-2-furfurylideneamino)-5-mercapto-1,2,4-triazoles (2a-g) and 7H-3-aryloxymethyl-6-(5-nitro-2-furyl)-s-triazolothiadiazines (3a-g).Most of the compounds of series 2 and 3 have been found to be active against both gram positive and gram negative bacteria at less than 5μg ml concentration.
Triazolocycloalkylthiadiazine derivatives
-
, (2008/06/13)
Novel triazolocycloalkylthiadiazines, their preparation, and use as antisecretory agents and central nervous system depressants.
Triazolocycloalkylhydrothiadiazine derivatives
-
, (2008/06/13)
Novel triazolocycloalkylhydrothiadiazines and their preparation, which are useful as antisecretory agents, central nervous system stimulants, and central nervous system depressants, are disclosed.
