Synthesis and diverse biological activity profile of triethylammonium isatin-3-hydrazones

Abstract

A series of biorelevant triethylammonium isatin hydrazones containing various substituents in the aromatic fragment have been synthesized. Their structure and composition were confirmed by NMR- and IR-spectroscopies, mass-spectrometry and elemental analysis. It was found that some representatives show activity against Staphylococcus aureus and Bacillus cereus higher or at the level of norfloxacin, including methicillin-resistant Staphylococcus aureus strains. The study also showed low hemo- and cytotoxicity (Chang Liver) and high antiaggregatory and anticoagulant activity of these compounds. The high potential of new ammonium isatin-3-acylhydrazones in the search for antimicrobial activity against phytopathogens of bacterial and fungal nature has been shown for the first time.

Anticancer and Antiphytopathogenic Activity of Fluorinated Isatins and Their Water-Soluble Hydrazone Derivatives

“…Fludioxonil and N-cetylpyridinium chloride showed a much greater effect of P. cactorum growth inhibition compared to F. oxysporum (2.8 and 4.1 times, respectively, for the two fungicides in Table 3). The behavior of the fluorine-free compounds synthesized and examined for antiphytopathogenic activity by us earlier [25] was in line with the latter tendency, i.e., they were similar to the reference fungicides. The results could testify to a promising synthetic strategy potentially resulting in the fluorine-containing hydrazones being uncommonly efficient vs. Fusarium oxysporum in comparison with known fungicides.…”

“…This is evidenced by recent reviews on the therapeutic possibilities of various quaternary ammonium compounds [18][19][20][21][22]. Earlier, we also demonstrated the high potential of isatin hydrazones containing a quaternary ammonium center in the search for drug candidates for combating human and plant diseases [23][24][25][26][27] (Figure 2). Another advantage of isatins as a promising platform for the design and development of new drugs is the possibility of introducing additional substituents at positions of the isatin ring.…”

“…In contrast to the reactions described in Scheme 1, the alkylation of sodium salt 2 by less electrophilic benzylic halides requires heating in order to achieve higher yields of the target compounds. In continuation of our research on the synthesis and biological activity of water-soluble isatin-3-acylhydrazones [for example, see [23][24][25][26], we also synthesized several new pyridinium acylhydrazones (5a-e) and previously published more lipophilic analogs (7ac) [26] (Figure 3) containing fluorine atoms in various molecular fragments (Scheme 3). The halogenated isatins 3a-f were isolated in high yields in their pure form immediately after the workup of the reaction mixtures.…”

“…In contrast to the reactions described in Scheme 1, the alkylation of sodium salt 2 by less electrophilic benzylic halides requires heating in order to achieve higher yields of the target compounds. In continuation of our research on the synthesis and biological activity of water-soluble isatin-3-acylhydrazones [for example, see [23][24][25][26], we also synthesized several new pyridinium acylhydrazones (5a-e) and previously published more lipophilic analogs (7ac) [26] (Figure 3) containing fluorine atoms in various molecular fragments (Scheme 3). In continuation of our research on the synthesis and biological activity of watersoluble isatin-3-acylhydrazones (for example, see [23][24][25][26]), we also synthesized several new pyridinium acylhydrazones (5a-e) and previously published more lipophilic analogs (7a-c) [26] (Figure 3) containing fluorine atoms in various molecular fragments (Scheme 3).…”

Recent advances and challenges in antibacterial drug development; The editorial

“…Balbina Plotkin and Monika Konaklieva discuss the “Impact of host factors on susceptibility to antifungal agents” [ 9 ]. Matthias Fellner presents “Newly discovered Staphylococcus aureus serine hydrolase probe and drug targets” [ 10 ] and Andrei Bogdanov, et al [ 11 ] describe a novel antibacterial scaffold in “Synthesis and diverse biological activity profile of triethylammonium isatin-3-hydrazones.”…”