148673-71-6Relevant articles and documents
Substituted amides of pyrazine-2-carboxylic acids: Synthesis and biological activity
Dolezal, Martin,Miletin, Miroslav,Kunes, Jiri,Kralova, Katarina
, p. 363 - 373 (2002)
Condensation of 6-chloro-, 5-tert-butyl- or 6-chloro-5-tert-butylpyrazine- 2-carboxylic acid chloride with ring substituted anilines yielded a series of amides, which were tested for their in vitro antimycobacterial, antifungal and photosynthesis-inhibiting activities. The highest antituberculotic activity (72% inhibition) against Mycobacterium tuberculosis and the highest lipophilicity (log P = 6.85) were shown by the 3,5-bis-trifluoromethylphenyl amide of 5-tert-butyl-6-chloropyrazine-2-carboxylic acid (2o). The 3-methylphenyl amides of 6-chloro- and 5-tert-butyl-6-chloro-pyrazine-2-carboxylic acid (2d and 2f) exhibited only a poor in vitro (antifungal effect (MIC = 31.25-500 μmol·dm-3) against all strains tested, although the latter was the most active antialgal compound (IC50 = 0.063 mmol·dm-3). The most active inhibitor of oxygen evolution rate in spinach chloroplasts was the (3,5-bis-trifluoromethylphenyl)amide of 6-chloropyrazine-2-carboxylic acid (2m, IC50 = 0.026 mmol·dm-3).
Vibrational spectroscopic studies and ab initio calculations of a substituted amide of pyrazine-2-carboxylic acid-C12H10ClN3O
Mary, Y. Sheeena,Varghese, Hema Tresa,Panicker, C. Yohannan,Dolezal, Martin
, p. 725 - 730 (2008)
A substituted amide of pyrazine-2-carboxylic acid was prepared and the IR spectrum is recorded and analysed. The vibrational frequencies and corresponding vibrational assignments are examined theoretically using the Gaussian03 set of quantum chemistry cod
Synthesis and Antimicrobial Evaluation of 6-Alkylamino-N-phenylpyrazine-2-carboxamides
Servusova-Vanaskova, Barbora,Paterova, Pavla,Garaj, Vladimir,Mandikova, Jana,Kunes, Jiri,Naesens, Lieve,Jílek, Petr,Dolezal, Martin,Zitko, Jan
, p. 674 - 681 (2015)
This work presents synthesis and antimicrobial evaluation of nineteen 6-alkylamino-N-phenylpyrazine-2-carboxamides. Antimycobacterial activity was determined against Mycobacterium tuberculosis H37Rv, M. kansasii and two strains of M. avium. Generally, the antimycobacterial activity increased with prolongation of simple alkyl chain and culminated in compounds with heptylamino substitution (3e, 4e) with MIC = 5-10 μm against M. tuberculosis H37Rv. On the contrary, derivatives with modified alkyl chain (containing e.g. terminal methoxy or hydroxy group) as well as phenylalkylamino derivatives were mainly inactive. The most active compounds (with hexyl to octylamino substitution) were evaluated for their in vitro activity against drug-resistant strains of M. tuberculosis and possessed activity comparable to that of the reference drug isoniazid. None of the tested compounds were active against M. avium. Some derivatives exhibited activity against Gram-positive bacteria including methicillin-resistant Staphylococcus aureus (best MIC = 7.8 μm), while Gram-negative strains as well as tested fungal strains were completely unsusceptible. Active compounds were tested for in vitro toxicity on various cell lines and in most cases were non-toxic up to 100 μm.
Substituted N-phenylpyrazine-2-carboxamides, their synthesis and evaluation as herbicides and abiotic elicitors
Dolezal, Martin,Tumova, Lenka,Kesetovicova, Diana,Tuma, Jiri,Kral'ova, Katarina
, p. 2589 - 2598 (2007)
The condensation of substituted pyrazine-2-carboxylic acid chlorides with ring-substituted anilines yielded five substituted pyrazine-2-carboxylic acid amides. The synthesis, and analytical, lipophilicity and biological data of the newly synthesized compo
Synthesis and in vitro evaluation of diverse heterocyclic diphenolic compounds as inhibitors of DYRK1A
Zhou, Qingqing,Reekie, Tristan A.,Abbassi, Ramzi H.,Indurthi Venkata, Dinesh,Font, Josep S.,Ryan, Renae M.,Munoz, Lenka,Kassiou, Michael
, p. 5852 - 5869 (2018/11/10)
Dual-specificity tyrosine phosphorylation-related kinase 1A (DYRK1A) is a dual-specificity protein kinase that catalyses phosphorylation and autophosphorylation. Higher DYRK1A expression correlates with cancer, in particular glioblastoma present within the brain. We report here the synthesis and biological evaluation of new heterocyclic diphenolic derivatives designed as novel DYRK1A inhibitors. The generation of these heterocycles such as benzimidazole, imidazole, naphthyridine, pyrazole-pyridines, bipyridine, and triazolopyrazines was made based on the structural modification of the lead DANDY and tested for their ability to inhibit DYRK1A. None of these derivatives showed significant DYRK1A inhibition but provide valuable knowledge around the importance of the 7-azaindole moiety. These data will be of use for developing further structure-activity relationship studies to improve the selective inhibition of DYRK1A.
Alkylamino derivatives of N-benzylpyrazine-2-carboxamide: synthesis and antimycobacterial evaluation
Servusova-Vanaskova, Barbora,Jandourek, Ondrej,Paterova, Pavla,Kordulakova, Jana,Plevakova, Magdalena,Kubicek, Vladimir,Kucera, Radim,Garaj, Vladimir,Naesens, Lieve,Kunes, Jiri,Dolezal, Martin,Zitko, Jan
supporting information, p. 1311 - 1317 (2015/07/15)
A series of alkylamino derivatives of N-benzylpyrazine-2-carboxamide was designed, synthesized and assayed in vitro for their antimycobacterial, antibacterial, antifungal as well as antiviral activities. Final structures were prepared from 6-chloro (1), 5-chloro (2) or 3-chloro (3) derivatives of N-benzylpyrazine-2-carboxamide by nucleophilic substitution of chlorine with n-alkylamines in the range from butylamine to octylamine (labelled a-e). Series 1a-e and 2a-e exerted higher activity against Mycobacterium tuberculosis H37Rv compared to the corresponding pattern compounds and the reference compound pyrazinamide. The most active derivatives reached an activity MIC = 4.6-10 μM (M. tbc H37Rv). More importantly, activity was also observed against other tested mycobacterial strains (including drug-resistant strains). Substitution of 3-chlorine was disadvantageous and led to completely inactive compounds 3a-e. Some compounds showed activity against Gram-positive bacterial strains (including MRSA) or influenza virus, but no antifungal activity was observed.
