Novel synthesis scheme and in vitro antimicrobial evaluation of a panel of (E)-2-aryl-1-cyano-1-nitroethenes

Abstract

(2016) Novel synthesis scheme and invitro antimicrobial evaluation of a panel of (E)-2-aryl-1-cyano-1-nitroethenes, Journal of Enzyme Inhibition and Medicinal Chemistry, 31:6, 900-907, DOI: 10.3109/14756366.2015 AbstractDrug resistance has become a major concern in the field of infection management, therefore searching for new antibacterial agents is getting more challenging. Our study presents an optimized and eco-friendly synthesis scheme for a panel of nitroalkenes bearing various functional groups in the aromatic moiety and bromine or cyano substituents in 1 position of nitrovinyl moiety. The presence of nitrolefine group outside the ring minimalizes genotoxic properties while conjugation of aryl group with nitrovinyl moiety increases stability of the compounds. Then our research focused on evaluation of biological properties of such obtained (E)-2-aryl-1-cyano-1-nitroethenes. As they exhibit strong bacteriostatic and bactericidal activities against reference bacteria and yeast species with no detectable cytotoxicity towards cultured human HepG2 and HaCaT cells, they could be promising candidates for the replacement of traditional nitrofurane-containing antibacterial drugs. Nevertheless, validation of the obtained data in an in vivo model and additional safety studies on mutagenicity are still required.

Unexpected course of reaction between (E)-2-aryl-1-cyano-1-nitroethenes and diazafluorene: why is there no 1,3-dipolar cycloaddition?

“…Nitroalkenes 1a – 1d [9, 11] and 6 [46] and diazafluorene ( 2 ) [45] were synthesized according to the procedures described earlier.…”

Understanding the mechanism of the decomposition reaction of nitroethyl benzoate through the Molecular Electron Density Theory

“…Applications of nitroalkenes in organic synthesis are largely due to their ease of conversion into a variety of functionalities. Moreover, a considerable number of nitroalkenes exhibits remarkable biological activity [12][13][14][15].…”

A DFT computational study on the [3+2] cycloaddition between parent thionitrone and nitroethene

“…11,12 Subsequently, it should be noted, that the presence of nitro-group in the organic molecule generally stimulates additive functions of bioactivity. [13][14][15][16] Furthermore, nitro-group is an exceedingly attractive starting point for further transformation into many important organic groups and moieties. [17][18][19][20] Nitroisothiazolidines can be prepared via [3+2] cycloaddition reaction involving thionitrones and conjugated nitroalkenes as addents.…”