32362-89-3

Usage

InChI:InChI=1/C7H6N4S/c12-7-9-6(10-11-7)5-3-1-2-4-8-5/h1-4H,(H2,9,10,11,12)

Upstream product

• 98-98-6 2-Picolinic acid 
• 2459-07-6 methyl pyridine-2-carboxylate 
• 1452-63-7 picolinic acid hydrazide 
• 374904-80-0 methyl 2-[amino(pyridin-3-yl)methylidene]hydrazinecarbodithioate 
• 1147550-11-5 ammonium thiocyanate 
• 79-19-6 thiosemicarbazide 
• 108921-63-7 morpholino(pyridin-2-yl)methanethione 
• 4923-12-0 (2-picoloylcarbonyl)thiosemicarbazone 

Relevant academic research and scientific papers

Discovery of [1,2,4]triazole derivatives as new metallo-β-lactamase inhibitors

The emergence and spread of metallo-β-lactamase (MBL)-mediated resistance to β-lactam antibacterials has already threatened the global public health. A clinically useful MBL inhibitor that can reverse β-lactam resistance has not been established yet. We here report a series of [1,2,4]triazole derivatives and analogs, which displayed inhibition to the clinically relevant subclass B1 (Verona integron-encoded MBL-2) VIM-2. 3-(4-Bromophenyl)-6,7-dihydro-5H-[1,2,4]triazolo [3,4-b][1,3]thiazine (5l) manifested the most potent inhibition with an IC50 (half-maximal inhibitory concentration) value of 38.36 μM. Investigations of 5l against other B1 MBLs and the serine β-lactamases (SBLs) revealed the selectivity to VIM-2. Molecular docking analyses suggested that 5l bound to the VIM-2 active site via the triazole involving zinc coordination and made hydrophobic interactions with the residues Phe61 and Tyr67 on the flexible L1 loop. This work provided new triazole-based MBL inhibitors and may aid efforts to develop new types of inhibitors combating MBL-mediated resistance.

N-Heterocyclic dicarboxylic acids: Broad-spectrum inhibitors of metallo-β-lactamases with co-antibacterial effect against antibiotic-resistant bacteria

In an effort to identify novel, broad-spectrum inhibitors against the metallo-β-lactamases (MβLs), several N-heterocyclic derivatives were tested as inhibitors of MβLs CcrA, ImiS, and L1, which are representative enzymes from the distinct MβL subclasses. Three N-heterocyclic dicarboxylic acid derivatives were competitive inhibitors of CcrA and L1, exhibiting K i values ≤2 μM, while only 2,4-thiazolidinedicarboxylic acid (1b) was a competitive inhibitor of ImiS. Two 2-mercapto-1,3,4-thiadiazole derivatives were noncompetitive inhibitors of CcrA and ImiS, exhibiting K i values 7 μM; however, these same compounds did not inhibit L1. Two 2-mercapto-1,3,4-triazole derivatives were shown not to inhibit any of the tested MβLs. The N-heterocyclic derivatives were tested for antibacterial activity by examining the MIC values for existing antibiotics in the presence/absence of these derivatives. Consistent with the steady-state inhibition data, the inclusion of three N-heterocyclic dicarboxylic acid derivatives resulted in lower MIC values when using Escherichia coli BL21(DE3) cells containing the CcrA or L1 plasmids or Klebsiella pneumoniae (ATCC 700603), while 1b was the only dicarboxylic acid derivative to lower the MIC value of E. coli cells containing the ImiS plasmid. Inclusion of the 2-mercapto-1,3,4- thiadiazole derivatives resulted in lower MIC values for E. coli cells containing ImiS or L1 plasmids; however, these derivatives did not alter the MIC values for K. pneumoniae or E. coli cells containing the L1 plasmid. None of the N-heterocyclic derivatives affected the MIC of two methicillin resistant Staphylococcus aureus (MRSA) strains. Taken together, these studies demonstrate that N-heterocyclic dicarboxylic acids 1a-c and pyridylmercaptothiadiazoles 2a,b are good scaffolds for future broad-spectrum inhibitors of the MβLs.

THIAZOLTRIAZOLES AND THIAZOLIMIDAZOLES AS ANTAGONISTS OF THE MGLUR5 RECEPTOR

This invention relates to novel thiazolotriazole and thiazoloimidazole derivatives of formula (I). The invention also relates to the use of the derivatives in treating diseases and conditions wherein antagonism of the mGluR5 receptor is beneficial, in particular substance related disorders. In addition, the invention relates to compositions containing the derivatives and processes for their preparation.

Reactivity of N1-dithioester substituted pyridinand pyrazincarboxamidrazones

The N1-dithioester substituted pyridin- and pyrazincarboxamidrazones underwent cyclocondensation to 5-methylsulfanyl-1,3,4- thiadiazole or 1,2,4-triazole derivatives, depending on the reaction conditions. With an excess of secondary amines, pyrazincarboxamidrazone dithioester gave 5-amino-1,3,4-thiadiazoles and with an ethanoloamine a 1,2,4-triazole derivative. Prepared compounds were evaluated as potential tuberculostatic agents, but the minimum inhibitory concentrations values indicated no significant activity. Copyright Taylor & Francis Group, LLC.

The reaction of N3-substituted amidrazones with ammonium thiocyanate

In the reaction of N3-substituted amidrazones [I-III] with ammonium thiocyanate in hydrochloric acid medium there are obtained the derivatives of thiosemicarbazone acid amides [VII-IX]. In the same conditions the amidrazones [IV-VI] gave 1,2,4-triazol derivatives [XI-XIII]. In acetone medium the reaction of amidrazone [IV] with ammonium thiocyanate leads to formation of the copmpound [X]. By the heating of the compounds [VII-X] in butanol there were obtained the derivatives of 1,2,4-triazoline-5-thione [XV-XVII].

STUDIES ON THIONAMIDES AND THEIR DERIVATIVES. PART XIII. 4-(2- AND 4-PYRIDYLCARBOTHIO)MORPHOLINE

Alkylation products of 4-(2-pyridylcarbothio)morpholine and 4-(4-pyridylcarbothio)morpholine were obtained.The reaction mechanism and the structures of obtained compounds were established, as well as their activity as compared with that of thiosemicarbazide, together with bacteriostatic and antimitotic activities of all compounds. Keywords: thionamides, spectral analysis, antimitotic activity.