Synthesis, surface and antimicrobial properties of some quaternary ammonium homochiral camphor sulfonamides

Mikláš, Roman; Miklášova, Natalia; Bukovský, Marián; Horváth, Branislav; Kubincová, Janka; Devı́nsky, Ferdinand

doi:10.1016/j.ejps.2014.08.013

Cited by 23 publications

(13 citation statements)

References 47 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…On the other hand, 1,7,7-trimethylbicycloĳ2.2.1]heptan scaffolds are structural units in numerous bioactive compounds such as camphor and borneol that possess different biological activity; for example, antimicrobial, 7 antiviral, [8][9][10] antioxidant, 11 analgesic 12 and receptor antagonist. 13 The structural features of this system such as gem-dimethyl group and conformationally rigid bicycle can modify the rotational barriers and stabilise a bioactive conformation and provide favourable van der Waals interactions with the binding site of the target protein.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antiviral activity of camphor-based 1,3-thiazolidin-4-one and thiazole derivatives as Orthopoxvirus-reproduction inhibitors

et al. 2018

View full text Add to dashboard Cite

show abstract

Section: Introductionmentioning

confidence: 99%

Synthesis and antiviral activity of camphor-based 1,3-thiazolidin-4-one and thiazole derivatives as Orthopoxvirus-reproduction inhibitors

et al. 2018

View full text Add to dashboard Cite

show abstract

“…Mikláš et al presented an interesting set of homochiral quaternary ammonium sulfonamides bearing hydrophobic camphor derived moieties [ 101 ]. The authors used commercially available (1 S )-(+)-camphor-10-sulfonic acid 125 ( Figure 32 ), as a precursor for targeted monoterpene-based sulphonamides molecules 126 – 128 ( Figure 32 ).…”

Section: Monoterpene Bicyclic Derivativesmentioning

confidence: 99%

Monoterpenes and Their Derivatives—Recent Development in Biological and Medical Applications

Zielińska-Błajet

Feder‐Kubis

2020

IJMS

217

View full text Add to dashboard Cite

Monoterpenes, comprising hydrocarbons, are the largest class of plant secondary metabolites and are commonly found in essential oils. Monoterpenes and their derivatives are key ingredients in the design and production of new biologically active compounds. This review focuses on selected aliphatic, monocyclic, and bicyclic monoterpenes like geraniol, thymol, myrtenal, pinene, camphor, borneol, and their modified structures. The compounds in question play a pivotal role in biological and medical applications. The review also discusses anti-inflammatory, antimicrobial, anticonvulsant, analgesic, antiviral, anticancer, antituberculosis, and antioxidant biological activities exhibited by monoterpenes and their derivatives. Particular attention is paid to the link between biological activity and the effect of structural modification of monoterpenes and monoterpenoids, as well as the introduction of various functionalized moieties into the molecules in question.

show abstract

“…Other compounds with alkyl chains shorter or longer than 16 or 17 carbon atoms were less active. As with numerous types of sets of compounds possessing long alkyl chains [1,2,46,51,52,53], the socalled cut-off effect [54] was observed. The Gram-negative bacteria E. coli was the strain most sensitive to compound 12.…”

Section: Antimicrobial Activitymentioning

confidence: 99%

Novel Phospholium‐Type Cationic Surfactants: Synthesis, Aggregation Properties and Antimicrobial Activity

Lukáč

Devı́nsky

Pisárčik

et al. 2016

J Surfact & Detergents

View full text Add to dashboard Cite

A series of novel phospholium amphiphilic compounds with straight alkyl chains with different numbers of carbon atoms (12,14,15,16,17,18) were synthesized. The quaternary phosphorus, phosphonium cation, is incorporated into a five-membered heterocyclic ring. Their physicochemical properties were investigated by measurements of surface tension, conductivity and dynamic light scattering. The critical micelle concentration (c M ), the surface tension value at the c M (c cmc ), the surface area at the surface saturation per head group (A cmc ), the ionization degree of micelle (a), the free energy of micellization (DG°m ic ), and hydrodynamic diameter (d h ) were determined. Antimicrobial activity was tested against bacteria and yeast. The structure-activity relationship was determined. 3 J CP = 17.3 Hz, = C-CH 3 ) 22.5 (d, 1 J CP = 46.2 Hz, a CH 2 of alkyl chain), 22.6 (d, 2 J CP = 4.1 Hz, b CH 2 of alkyl chain), 22.7 (x CH 2 of alkyl chain), 29.1, 29.3, 29.4, 29.5, 29.6(0), 29.6(4), 29.7 (d-x-2 CH 2 of alkyl chain), 30.5 (d, 3 J CP = 15.6 Hz, c CH 2 of alkyl chain), 31.9 (x-1 CH 2 of alkyl chain), 113.6 (d, 1 J CP = 80.0 Hz, = CHP), 115.9 (d, 1 J CP = 83.9 Hz, Ph C 1 ), 130.0 (d, 3 J CP = 12.9 Hz, Ph C meta ), 133.6 (d, 2 J CP = 10.7 Hz, Ph C ortho ), 134.6 (d, 4 J CP = 3.0 Hz, Ph C para ), 163.2 (d, 2 J CP = 16.4 Hz, = C-CH 3 ); 31 P NMR (CDCl 3 , H 3 PO 4 ) d: 38.5; IR t max /cm -H NMR (CDCl 3 , TMS) d: 0.88 (t, 3 J H,H = 6.7 Hz, 3H, CH 3 of alkyl chain), 1.13-1.38 (m, 22H, 11 9 CH 2 of alkyl chain), 1.38-1.62 (m, 4H, b, c CH 2 of alkyl chain) 2.29 (s, 6H, 2 9 = C-CH 3 ), 3.08-3.22 (m, 2H, a CH 2 of alkyl chain), 7.08 (d, 2 J HP = 30.9 Hz, 2H, = CHP), 7.54-7.61 (m, 2H, Ph H meta ), 7.61-7.75 (m, 1H, Ph H para ), 8.15-8.23 (m, 2H, Ph H ortho ); 13 C NMR (CDCl 3 , TMS) d: 14.1 (CH 3 of alkyl chain), 18.5 (d, 3 J CP = 17.3 Hz, = C-CH 3 ) 22.5 (d, 1 J CP = 46.1 Hz, a CH 2 of alkyl chain), 22.6 (d, 2 J CP = 4.1 Hz, b CH 2 of alkyl chain), 22.7 (x CH 2 of alkyl chain), 29.1, 29.3, 29.4, 29.5, 29.6, 29.7 (d-x-2 CH 2 of alkyl chain), 30.5 (d, 3 J CP = 15.4 Hz, c CH 2 of alkyl chain), 31.9 (x-1 CH 2 of alkyl chain), 113.6 (d, 1 J CP = 80.0 Hz, = CHP), 115.8 (d, 1 J CP = 83.8 Hz, Ph C 1 ), 130.0 (d, 3 J CP = 12.9 Hz, Ph C meta ), 133.5 (d, 2 J CP = 10.4 Hz, Ph C ortho ), 134.7 (d, 4 J CP = 3.0 Hz, Ph C para ), 163.2 (d, 2 J CP = 16.5 Hz, = C-CH 3 ); 31 P NMR (CDCl 3 , H 3 PO 4 ) d: 38.5; IR t max /cm -

show abstract

Synthesis, surface and antimicrobial properties of some quaternary ammonium homochiral camphor sulfonamides

Cited by 23 publications

References 47 publications

Synthesis and antiviral activity of camphor-based 1,3-thiazolidin-4-one and thiazole derivatives as Orthopoxvirus-reproduction inhibitors

Synthesis and antiviral activity of camphor-based 1,3-thiazolidin-4-one and thiazole derivatives as Orthopoxvirus-reproduction inhibitors

Monoterpenes and Their Derivatives—Recent Development in Biological and Medical Applications

Novel Phospholium‐Type Cationic Surfactants: Synthesis, Aggregation Properties and Antimicrobial Activity

Contact Info

Product

Resources

About