Sulfenimines′ Synthesis and Antimicrobial Activity Based on Pinane Hydroxythiols

Priya Toth^*
*Correspondence: Priya Toth, Department of Molecular Microbiology, Microbiology Icahn School of Medicine at Mount Sinai, New York, USA, Email:

Description

The widespread occurrence of pathogenic microorganisms that are multidrug resistant presents a challenge for the development of novel chemotype antimicrobials that are resistant to microbial tools of resistance. Numerous monoterpenoids have been demonstrated to have antimicrobial potential thus far. Terpenes and terpenoids are among many classes of molecules with antimicrobial activity and because of their low toxicity and ability to undergo various modifications; they make an appealing starting point for the development of antimicrobials. The synthesis of sulfenimines from chiral trifluoromethylated and non-fluorinated pinane-type thiols is described in this work. Yields of up to 81% were achieved for the final compounds. Three of the sulfenimines discovered had between and could inhibit the growth of both bacteria and fungi the widespread presence of multidrug-resistant bacteria and fungi complicates the development of novel chemotype antimicrobials, as they are immune to microbial resistance tools. Changes in target molecules and cell wall structure, as well as the acquisition of genes encoding efflux systems and enzymes that hydrolyse antimicrobials [1-3].

Monoterpene derivatives have a broad spectrum of antimicrobial activity among the various classes of molecules capable of inhibiting the growth of pathogenic bacteria and fungi. As a result, the inhibition of the growth of various bacteria and fungi has been reported Terpenes increase the activity of conventional antimicrobials when combined with them Furthermore, the fusion of a biologically active molecule in on Carine sulfenimines, sulfinimines and N-substituted fluorine-containing sulphonamides, as well as pinnae thiosulfates synthesised from monoterpene thiols, exhibited selective antimicrobial activity against the yeasts Candida albinos and Cryptococcus neoformans, as well as the bacteria Staphylococcus aureus and Aconite The presence of a sulfenimine fragment in the structure of cephalosporin sulfoxides increased their inhibitory activity against cephalosporin’s C. Substituents in the sulfenimine moiety had a significant effect on activity. Substituted salicylic and nitrobenzylidene imines have been shown to be tested as new antimicrobial drug candidate chemo type. Nowadays, one-third of newly synthesised antimicrobials contain fluorine atoms because the addition of fluorine-containing groups increases membrane permeability and resistance to biodegradation compared to their no fluorinated analogues When compared to hydrocarbon analogues, these changes can result in significant changes in the target's interaction mechanisms with the drug, as well as shifts in the latter's biological activity Previously, Containing pinnae-type monoterpene hydroxyethyls were synthesised for further functionalization. Based on 10-hydroxyisopinocampheyl thiol which was previously obtained by our group and nitro benzaldehydes or substituted salicylic aldehydes, a series of sulfenimines were synthesised and their antibacterial and antifungal activities, cytotoxicity and mutagenicity were evaluated. The minimum inhibitory concentrations of compounds were determined in full Mueller-Hinton broth using the broth microdilution assay in 96-well plates according to the rules for antimicrobial susceptibility testing In brief, a bacterial suspension containing 108 was diluted to 1:300 with MH broth in microcell plates to yield a suspension, which was then incubated at 37 °C for 24 hours. Stock solutions of compounds to be tested in were prepared and added to final concentrations of compounds to be tested ranging The was calculated as the lowest antibiotic concentration at which no visible bacterial growth could be Compounds' mutagenicity was assessed using the Ames test with S. typhimurium strains, as described in The spot-test modification was used to avoid false-negative results caused by compounds' antibacterial activity. If the number of revert ant colonies increased more than twice when the compound was close to the filter paper, the compound was considered mutagenic [4,5].

Conclusion

Cells the cytotoxicity of compounds was determined using the cells were cultured in supplemented with 10% FBS, 2 mm L-glutamine, penicillin and 100 g/mL streptomycin Cells were seeded at a density of cells per well in 96-well plates. IR spectra were recorded in a thin layer or in Kerr pellets using a infrared Fourier spectrometer. The spectra were recorded in using the signal of the indicated solvent as an internal standard on a Bruker Advance 300 spectrometer and heteronuclear experiments were used to complete the assignment of. Spectra of were recorded in using a Bruker spectrometer and an Ultra spectrometer with the signal of as an external standard. To facilitate interpretation Thus, for the first time, new monoterpene sulfenimines based on monoterpene pinnae thiols, including those containing a group, have been synthesised. In general, the sulfenimines described here have moderate antibacterial and antifungal activity and high cytotoxicity in vitro, limiting their direct application. The effects of monoterpene and aromatic moieties on the antimicrobial activity of sulfenimines, on the other hand, allow for further modelling of compounds with known selectivity for pathogenic microorganisms.

Acknowledgement

None.

Conflict of Interest

None.

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