75919-78-7Relevant academic research and scientific papers
Design, synthesis and anti-mycobacterial evaluation of some new N-phenylpyrazine-2-carboxamides
Zitko, Jan,Barbora, Servusova-Vanaskova,Paterova, Pavla,Navratilova, Lucie,Trejtnar, Frantisek,Kunes, Jiri,Dolezal, Martin
, p. 649 - 657 (2016/03/05)
N-Phenylpyrazine-2-carboxamides (anilides of pyrazinoic acids with simple substituents in various positions) were previously shown to possess significant biological activities in vitro, markedly anti-mycobacterial and photosynthesis-inhibiting activity. Based on structure-activity relationships (SAR) extracted from previously published series, 25 new anilides of non-substituted pyrazinoic acid (POA), 5-CH3-POA, 6-Cl-POA, 5-tert-butyl-POA and 5-tert-butyl-6-Cl-POA were designed and synthesised. The phenyl part was substituted with simple hydrophobic substituents chosen from methyl and halogens. 5-tert-Butyl-N-(5-fluoro-2-methylphenyl)pyrazine-2-carboxamide (9), N-(3-chloro-4-methylphenyl)-5-methylpyrazine-2-carboxamide (12), 6-chloro-N-(3-chloro-4-methylphenyl)pyrazine-2-carboxamide (13) and 6-chloro-N-(5-iodo-2-methylphenyl)pyrazine-2-carboxamide (18) possessed whole cell anti-mycobacterial activity in vitro against Mycobacterium tuberculosis H37Rv with minimum inhibitory concentration (MIC) of around 10 μM. Importantly, no cytotoxicity in the HepG2 model was detected in vitro at the concentrations tested and the estimated IC50 values were in hundreds of μM, indicating promising selectivity. N-(3-Chloro-4-methylphenyl)pyrazine-2-carboxamide (11) and N-(4-chloro-2-iodophenyl)pyrazine-2-carboxamide (21) exerted significant activity against Mycobacterium kansasii with MIC 12.6 μM and 8.7 μM, respectively. No activity was detected against Mycobacterium avium. SAR were in accordance with those observed for the derivatives previously published.
Halogen bonding synthon modularity in coordination compounds
Khavasi, Hamid Reza,Norouzi, Fataneh,Azhdari Tehrani, Alireza
, p. 2579 - 2583 (2015/06/16)
In this Communication, the modulation of halogen bonding synthons in the crystal structure of [HgBr2(L3,4-diCl)] from [HgBr2(L3-Cl)] and [HgBr2(L4-Cl)], as single components, where L is a N
Effect of halogen bonding interaction on supramolecular assembly of halogen-substituted phenylpyrazinamides
Khavasi, Hamid Reza,Tehrani, Alireza Azhdari
, p. 3222 - 3235 (2013/06/27)
A series of halogen-substituted phenylpyrazinamides have been synthesized and crystallographically characterized in order to investigate the effect of halogen bonding interaction on supramolecular assembly of N-phenylpyrazine-2- carboxamide derivatives. The notable feature in crystal structures of meta- and para-iodinated, brominated and chlorinated compounds is that there is a tendency to form a halogen bonding synthon between adjacent halophenyl and prazine/halophenyl rings. Influence of these halogen bonding interactions on supramolecular assemblies have been discussed with the help of geometrical analysis and theoretical calculations. The X...N halogen bonding distances are 2.2-7.7% shorter than the sum of the van der Waals radii of the nitrogen and halogen atoms. Also, theoretical methods show the N...X halogen bonding energies within a range of -9.43 to -23.67 kJ mol-1. Our studies show that the selection of halogen atom as well as the position of substitution on phenylpyrazinamide compound may be important for crystal design based on halogen bonding.
Synthesis and antitubercular evaluation of N-Arylpyrazine and N,Na-Alkyl-diylpyrazine-2-carboxamide derivatives
Bispo, Marcelle De Lima Ferreira,Goncalves, Raoni Schroeder Borges,Lima, Camilo Henrique Da Silva,Cardoso, Laura Nogueira De Faria,Lourenco, Maria Cristina Silva,De Souza, Marcus Vinicius Nora
, p. 1317 - 1322 (2013/02/22)
Two series of pyrazinamide (PZA) derivatives have been synthesized and evaluated for their in vitro antibacterial activity against Mycobacterium tuberculosis H37Rv. Some compounds exhibited minimum inhibitory concentration activity of 50-100 μg/mL, greater than the first line antituberculosis drug PZA in Alamar Blue assay (>100 μg/mL). The obtained activities can be considered promising results, which characterizes these compounds as good start points to development of new antitubercular agents.
Synthesis, antimycobacterial, antifungal and photosynthesis-inhibiting activity of chlorinated N-phenylpyrazine-2-carboxamides
Dolezal, Martin,Zitko, Jan,Osicka, Zdenek,Kunes, Jiri,Vejsova, Marcela,Buchta, Vladimir,Dohnal, Jiri,Jampilek, Josef,Kralova, Katarina
experimental part, p. 8567 - 8581 (2011/03/20)
A series of sixteen pyrazinamide analogues with the -CONH- linker connecting the pyrazine and benzene rings was synthesized by the condensation of chlorides of substituted pyrazinecarboxylic acids with ring-substituted (chlorine) anilines. The prepared compounds were characterized and evaluated for their antimycobacterial and antifungal activity, and for their ability to inhibit photosynthetic electron transport (PET). 6-Chloro-N-(4-chlorophenyl) pyrazine-2-carboxamide manifested the highest activity against Mycobacterium tuberculosis strain H37Rv (65% inhibition at 6.25 μg/mL). The highest antifungal effect against Trichophyton mentagrophytes, the most susceptible fungal strain tested, was found for 6-chloro-5-tert-butyl-N-(3,4-dichlorophenyl) pyrazine-2-carboxamide (MIC = 62.5 μmol/L). 6-Chloro-5-tert-butyl-N-(4- chlorophenyl)pyrazine-2-carboxamide showed the highest PET inhibition in spinach chloroplasts (Spinacia oleracea L.) chloroplasts (IC50 = 43.0 μmol/L). For all the compounds, the relationships between the lipophilicity and the chemical structure of the studied compounds as well as their structureactivity relationships are discussed.
