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Pyrazine Derivatives
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Pyrazine Derivatives

A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (30 June 2020) | Viewed by 14874

Special Issue Editor

Dr. Maria João Queiroz

E-Mail Website
Guest Editor
Centro de Química, Universidade do Minho (CQ/UM), Campus de Gualtar, 4710-057 Braga, Portugal
Interests: metal-catalyzed reactions (cross-couplings, C-H activation, and carbonylations); nucleophilic aromatic substitution; synthesis of heterocycles of N and/or S; antitumoral and anti-angiogenic compounds
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Pyrazine and its derivatives constitute an important class of heterocyclic compounds that are present in many natural products and can be synthesized chemically or biologically. They are important components of aroma fragrances and widely used as agrochemicals. Pyrazine-containing drugs are also extensively used for different therapeutic purposes. Besides that, pyrazine derivatives have applications as dyes, electroluminescent materials, organic semi-conductors, and as suitable ligands in coordination chemistry.

The pyrazine nucleus is present in many polycyclic compounds of biological significance such as quinoxalines and phenazines and bio-luminescent natural products such as pteridines and flavins. Condensed systems containing pyrazine and other heterocyclic scaffolds have given rise to compounds with several biological activities.

Researchers in the field are cordially invited to submit relevant manuscripts to the synthesis of pyrazine derivatives and their use in the construction of condensed systems for a Special Issue, ‘Pyrazine Derivatives’, within the journal Molecules. Moreover, contributions regarding their potential applications are also welcome.

Prof. Dr. Maria João Queiroz
Guest Editor

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Keywords

  • Pyrazine derivatives
  • Heterocyclic fused pyrazine derivatives
  • Metal-catalyzed reactions
  • Nucleophilic aromatic substitution
  • Green methodologies
  • Potential applications

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Published Papers (3 papers)

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Research

29 pages, 6536 KiB  
Article
N-Pyrazinoyl Substituted Amino Acids as Potential Antimycobacterial Agents—the Synthesis and Biological Evaluation of Enantiomers
by Martin Juhás, Lucie Kučerová, Ondřej Horáček, Ondřej Janďourek, Vladimír Kubíček, Klára Konečná, Radim Kučera, Pavel Bárta, Jiří Janoušek, Pavla Paterová, Jiří Kuneš, Martin Doležal and Jan Zitko
Molecules 2020, 25(7), 1518; https://doi.org/10.3390/molecules25071518 - 27 Mar 2020
Cited by 5 | Viewed by 3897
Abstract
Tuberculosis is an infectious disease caused by Mycobacterium tuberculosis (Mtb), each year causing millions of deaths. In this article, we present the synthesis and biological evaluations of new potential antimycobacterial compounds containing a fragment of the first-line antitubercular drug pyrazinamide (PZA), coupled with [...] Read more.
Tuberculosis is an infectious disease caused by Mycobacterium tuberculosis (Mtb), each year causing millions of deaths. In this article, we present the synthesis and biological evaluations of new potential antimycobacterial compounds containing a fragment of the first-line antitubercular drug pyrazinamide (PZA), coupled with methyl or ethyl esters of selected amino acids. The antimicrobial activity was evaluated on a variety of (myco)bacterial strains, including Mtb H37Ra, M. smegmatis, M. aurum, Staphylococcus aureus, Pseudomonas aeruginosa, and fungal strains, including Candida albicans and Aspergillus flavus. Emphasis was placed on the comparison of enantiomer activities. None of the synthesized compounds showed any significant activity against fungal strains, and their antibacterial activities were also low, the best minimum inhibitory concentration (MIC) value was 31.25 µM. However, several compounds presented high activity against Mtb. Overall, higher activity was seen in derivatives containing l-amino acids. Similarly, the activity seems tied to the more lipophilic compounds. The most active derivative contained phenylglycine moiety (PC-d/l-Pgl-Me, MIC < 1.95 µg/mL). All active compounds possessed low cytotoxicity and good selectivity towards Mtb. To the best of our knowledge, this is the first study comparing the activities of the d- and l-amino acid derivatives of pyrazinamide as potential antimycobacterial compounds. Full article
(This article belongs to the Special Issue Pyrazine Derivatives)
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20 pages, 5519 KiB  
Article
Substituted N-(Pyrazin-2-yl)benzenesulfonamides; Synthesis, Anti-Infective Evaluation, Cytotoxicity, and In Silico Studies
by Ghada Bouz, Martin Juhás, Lluis Pausas Otero, Cristina Paredes de la Red, Ondřej Janďourek, Klára Konečná, Pavla Paterová, Vladimír Kubíček, Jiří Janoušek, Martin Doležal and Jan Zitko
Molecules 2020, 25(1), 138; https://doi.org/10.3390/molecules25010138 - 29 Dec 2019
Cited by 12 | Viewed by 4977
Abstract
We prepared a series of substituted N-(pyrazin-2-yl)benzenesulfonamides as an attempt to investigate the effect of different linkers connecting pyrazine to benzene cores on antimicrobial activity when compared to our previous compounds of amide or retro-amide linker type. Only two compounds, 4-amino-N [...] Read more.
We prepared a series of substituted N-(pyrazin-2-yl)benzenesulfonamides as an attempt to investigate the effect of different linkers connecting pyrazine to benzene cores on antimicrobial activity when compared to our previous compounds of amide or retro-amide linker type. Only two compounds, 4-amino-N-(pyrazin-2-yl)benzenesulfonamide (MIC = 6.25 μg/mL, 25 μM) and 4-amino-N-(6-chloropyrazin-2-yl)benzenesulfonamide (MIC = 6.25 μg/mL, 22 μM) exerted good antitubercular activity against M. tuberculosis H37Rv. However, they were excluded from the comparison as they—unlike the other compounds—possessed the pharmacophore for the inhibition of folate pathway, which was proven by docking studies. We performed target fishing, where we identified matrix metalloproteinase-8 as a promising target for our title compounds that is worth future exploration. Full article
(This article belongs to the Special Issue Pyrazine Derivatives)
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19 pages, 1401 KiB  
Article
Derivatives of 3-Aminopyrazine-2-carboxamides: Synthesis, Antimicrobial Evaluation, and in Vitro Cytotoxicity
by Ghada Bouz, Lucia Semelková, Ondřej Janďourek, Klára Konečná, Pavla Paterová, Lucie Navrátilová, Vladimír Kubíček, Jiří Kuneš, Martin Doležal and Jan Zitko
Molecules 2019, 24(7), 1212; https://doi.org/10.3390/molecules24071212 - 28 Mar 2019
Cited by 12 | Viewed by 4625
Abstract
We report the design, synthesis, and in vitro antimicrobial activity of a series of N-substituted 3-aminopyrazine-2-carboxamides with free amino groups in position 3 on the pyrazine ring. Based on various substituents on the carboxamidic moiety, the series is subdivided into benzyl, alkyl, [...] Read more.
We report the design, synthesis, and in vitro antimicrobial activity of a series of N-substituted 3-aminopyrazine-2-carboxamides with free amino groups in position 3 on the pyrazine ring. Based on various substituents on the carboxamidic moiety, the series is subdivided into benzyl, alkyl, and phenyl derivatives. The three-dimensional structures of the title compounds were predicted using energy minimization and low mode molecular dynamics under AMBER10:EHT forcefield. Compounds were evaluated for antimycobacterial, antibacterial, and antifungal activities in vitro. The most active compound against Mycobacterium tuberculosis H37Rv (Mtb) was 3-amino-N-(2,4-dimethoxyphenyl)pyrazine-2-carboxamide (17, MIC = 12.5 µg/mL, 46 µM). Antimycobacterial activity against Mtb and M. kansasii along with antibacterial activity increased among the alkyl derivatives with increasing the length of carbon side chain. Antibacterial activity was observed for phenyl and alkyl derivatives, but not for benzyl derivatives. Antifungal activity was observed in all structural subtypes, mainly against Trichophyton interdigitale and Candida albicans. The four most active compounds (compounds 10, 16, 17, 20) were evaluated for their in vitro cytotoxicity in HepG2 cancer cell line; only compound 20 was found to exert some level of cytotoxicity. Compounds belonging to the current series were compared to previously published, structurally related compounds in terms of antimicrobial activity to draw structure activity relationships conclusions. Full article
(This article belongs to the Special Issue Pyrazine Derivatives)
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