Reactions of 1-(5-nitro-2-furyl)-2-nitroethylene with amino and hydroxy groups

Rosenberg, Michal; Šturdı́k, Ernest; Liptaj, Tibor; Bella, Juraj; Végh, Dániel; Považanec, František; Sitkey, V.

doi:10.1135/cccc19850470

Cited by 11 publications

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“…Just like other vinylfurans (2-furylethylenes), it is a thiolreactive compound and reacts with functional thiol groups in living cells, including those of vital enzymes48910. The reaction center of vinylfurans in these addition reactions is the electrophilic exocyclic double bond911. For example, G1 has been shown to react with the cysteine residues of MurA, a protein that is crucial to peptidoglycan synthesis and is the target of phosphomycin4.…”

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confidence: 99%

Antibacterial activity of the nitrovinylfuran G1 (Furvina) and its conversion products

Allas

Toom

Selyutina

et al. 2016

Sci Rep

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2-Bromo-5-(2-bromo-2-nitrovinyl)furan (G1 or Furvina) is an antimicrobial with a direct reactivity against thiol groups. It is active against Gram-positive and Gram-negative bacteria, yeasts and filamentous fungi. By reacting with thiol groups it causes direct damage to proteins but, as a result, is very short-living and interconverts into an array of reaction products. Our aim was to characterize thiol reactivity of G1 and its conversion products and establish how much of antimicrobial and cytotoxic effects are due to the primary activity of G1 and how much can be attributed to its reaction products. Stability of G1 in growth media as well as its conversion in the presence of thiols was characterized. The structures of G1 decomposition products were determined using NMR and mass-spectroscopy. Concentration- and time-dependent killing curves showed that G1 is bacteriostatic for Escherichia coli at the concentration of 16 μg/ml and bactericidal at 32 μg/ml. However, G1 is inefficient against non-growing E. coli. Addition of cysteine to medium reduces the antimicrobial potency of G1. Nevertheless, the reaction products of G1 and cysteine enabled prolonged antimicrobial action of the drug. Therefore, the activity of 2-bromo-5-(2-bromo-2-nitrovinyl)furan is a sum of its immediate reactivity and the antibacterial effects of the conversion products.

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confidence: 99%

Antibacterial activity of the nitrovinylfuran G1 (Furvina) and its conversion products

Allas

Toom

Selyutina

et al. 2016

Sci Rep

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Bond‐extended stochastic and nonstochastic bilinear indices. I. QSPR/QSAR applications to the description of properties/activities of small‐medium size organic compounds

Marrero-Ponce

Martínez

Casañola-Martín

et al. 2010

Int J of Quantum Chemistry

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Bond-extended stochastic and nonstochastic bilinear indices are introduced in this article as novel bond-level molecular descriptors (MDs). These novel totals (whole-molecule) MDs are based on bilinear maps (forms) similar to use defined in linear algebra. The proposed nonstochastic indices try to match molecular structure provided by the molecular topology by using the kth Edge(Bond)-Adjacency Matrix (E k , designed here as a nonstochastic E matrix). The stochastic parameters are computed by using the kth stochastic edge-adjacency matrix, ES k , as matrix operators of bilinear transformations. This new edge (bond)-adjacency relationship can be obtained directly from E k and can be considered like a new matrix-transformation strategic to obtain new relations for a molecular graph. In both set of MDs, chemical information is codified by using different pair combinations of atomic weightings (in this case four atomic-labels: atomic mass, polarizability, van der Waals volume, and electronegativity). In addition, a local-fragment (bond-type) formalism was also developed. The kth bond-type bilinear indices are calculated by summing the kth bond bilinear indices of all bonds of the same bond type in the molecules. The new set of MDs can be easily and quickly calculated in our in house software TOMOCOMD-CARDD (topological molecular computational design computer-aided-rational-drug design). The reported application and utilization of these MDs for predictive capability correlations of structure with physicochemical and pharmacological properties are reviewed. Three benchmark datasets have been used to evaluate the QSPR/QSAR behavior of the new bond-level TOMOCOMD-CARDD MDs. We developed the QSPR models to describe several physicochemical properties of octane isomers (First Case) and, to analyze of the boiling point of 28 alkyl-alcohols (Second Case) and to examine of the specific rate constant (log k), the partition coefficient (log P), as well as the antibacterial activity of 34 derivatives of 2-furylethylenes (Third Case). For these three rounds, the quantitative models found are significant from a statistical point of view and permit a clear interpretation of the studied properties in terms of the structural features of molecules. A leave-one-out cross-validation procedure revealed that the regression models had a good predictability. The comparison with other approaches reveals good performance of the method proposed. Therefore, it is clearly demonstrated that this suitability is higher than that shown by other 2D/3D well-known sets of MDs. The approach described here appears to be a very promising structural invariant, useful for QSPR/QSAR studies and shown to provide an excellent alternative or guides for discovery and optimization of new lead compounds, reducing the time and cost of the traditional procedure.

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Inhibition of (Na/K)-ATPase by electrophilic substances: Functional implications

Breier

Ziegelhöffer

Stankovičová

et al. 1995

Cellular Interactions in Cardiac Pathophysiology

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Reactions of 1-(5-nitro-2-furyl)-2-nitroethylene with amino and hydroxy groups

Cited by 11 publications

References 0 publications

Antibacterial activity of the nitrovinylfuran G1 (Furvina) and its conversion products

Antibacterial activity of the nitrovinylfuran G1 (Furvina) and its conversion products

Bond‐extended stochastic and nonstochastic bilinear indices. I. QSPR/QSAR applications to the description of properties/activities of small‐medium size organic compounds

Inhibition of (Na/K)-ATPase by electrophilic substances: Functional implications

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