320582-39-6Relevant academic research and scientific papers
An Efficient Greener Approach for N-acylation of Amines in Water Using Benzotriazole Chemistry
Ibrahim, Tarek S.,Seliem, Israa A.,Panda, Siva S.,Al-Mahmoudy, Amany M.M.,Abdel-Samii, Zakaria K.M.,Alhakamy, Nabil A.,Asfour, Hani Z.,Elagawany, Mohamed
, (2020/06/17)
A straightforward, mild and cost-efficient synthesis of various arylamides in water was accomplished using versatile benzotriazole chemistry. Acylation of various amines was achieved in water at room temperature as well as under microwave irradiation. The developed protocol unfolds the synthesis of amino acid aryl amides, drug conjugates and benzimidazoles. The environmentally friendly synthesis, short reaction time, simple workup, high yields, mild conditions and free of racemization are the key advantages of this protocol.
Strengthening N...X halogen bonding via nitrogen substitution in the aromatic framework of halogen-substituted arylpyrazinamides
Khavasi, Hamid Reza,Hosseini, Mahdieh,Tehrani, Alireza Azhdari,Naderi, Soheila
, p. 4546 - 4553 (2014/05/20)
The importance of N...X halogen bonding in a series of N-(5-halo-2-pyridinyl)pyrazine-2-carboxamides has been investigated by different methods. The results show that when nitrogen is substituted for carbon in the aryl backbone of the parent compound, it can affect the electron accepting ability of bromine and iodine substituents. Thus, a stronger halogen bond can be formed. This journal is the Partner Organisations 2014.
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.
Preparation of pyrazine carboxamides: A reaction involving N-heterocyclic carbene (NHC) intermediates
Naredla, Rajasekhar Reddy,Dash, Barada P.,Klumpp, Douglas A.
supporting information, p. 4806 - 4809 (2013/10/08)
In the reactions of 2,3-pyrazinedicarboxylic anhydride with amines and anilines, pyrazine carboxamides are formed in good to excellent yields. A mechanism is proposed involving ring opening of the anhydride and decarboxylation of the heterocyclic ring. Based on other similar heterocyclic decarboxylations, this suggests the involvement of an N-heterocyclic carbene intermediate leading to the product.
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 and antimycobacterial evaluation of substituted pyrazinecarboxamides
Dolezal, Martin,Cmedlova, Pavlina,Palek, Lukas,Vinsova, Jarmila,Kunes, Jiri,Buchta, Vladimir,Jampilek, Josef,Kralova, Katarina
, p. 1105 - 1113 (2008/09/20)
Unsubstituted, halogenated and/or alkylated pyrazine-2-carboxylic acid amides connected via -CONH- bridge with substituted anilines were synthesized using currently known synthetic pathways. The synthetic approach, analytical, spectroscopic, lipophilicity and biological data of 20 newly synthesized compounds are presented. Structure-activity relationships among the chemical structures, the antimycobacterial, antifungal, photosynthesis inhibiting and antialgal activity of the evaluated substituted N-phenylpyrazine-2-carboxamides are discussed. 5-tert-Butyl-6-chloro-N-(3-trifluoromethylphenyl)pyrazine-2-carboxamide (19) has shown the highest activity against Mycobacterium tuberculosis H37Rv (MIC = 3.13 μg/mL). The highest antifungal effect against Trichophyton mentagrophytes, the most susceptible fungal strain tested, was found for N-(3-trifluoromethylphenyl)pyrazine-2-carboxamide (14, MIC = 62.5 μmol/mL). The highest reduction of chlorophyll content in Chlorella vulgaris was found for pyrazine-2-carboxylic acid (3-trifluoromethylphenyl)amide (9, IC50 = 12.1 μmol/L).
