Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids
Optimizacija sinteze i in vitro proučavanje antimikrobnog dejstva α,β-nezasićenih i α-bromkarboksilnih kiselina
Abstract
A series of α,β-unsaturated and α-bromo carboxylic acids were identified as potent antimicrobial agents. The antimicrobial activity was evaluated using the broth microdilution method. All acids 1-12 exhibited a significant activity against nine laboratory control strains of bacteria and two strains of yeast Candida albicans. The tested acids were efficiently prepared by optimized phase-transfer-catalyzed (PTC) reactions of ketones with bromoform and aqueous lithium hydroxide in alcoholic solvent with triethylbenzyl ammonium chloride (TEBA) as catalyst.
U ovom radu je prikazano in vitro ispitivanje antimikrobnog dejstva serije α,β-nezasićenih i α-bromkarboksilnih kiselina i pokazano je da su one potencijalno dobri antimikrobni agensi. Sve kiseline 1-12 pokazale su značajnu aktivnost prema devet sojeva bakterija i dva soja gljivica Candida albicans. Ispitivane kiseline sintetisane su u optimizovanoj reakciji ketona sa bromoformom i litijum-hidroksidom u smesi rastvarača (terc-butanol/voda). Kao katalizator za prenos između faza upotrebljen je trietilbenzilamonijum-hlorid (TEBA).
Keywords:
antimicrobial activity / one-pot synthesis / ketones / bromoformSource:
Journal of the Serbian Chemical Society, 2012, 77, 6, 741-750Publisher:
- Srpsko hemijsko društvo, Beograd
Funding / projects:
DOI: 10.2298/JSC111104016V
ISSN: 0352-5139
WoS: 000306093300004
Scopus: 2-s2.0-84864535005
Collections
Institution/Community
PharmacyTY - JOUR AU - Vitnik, Vesna AU - Milenković, Marina AU - Dilber, Sanda AU - Vitnik, Željko J. AU - Juranić, Ivan O. PY - 2012 UR - https://farfar.pharmacy.bg.ac.rs/handle/123456789/1832 AB - A series of α,β-unsaturated and α-bromo carboxylic acids were identified as potent antimicrobial agents. The antimicrobial activity was evaluated using the broth microdilution method. All acids 1-12 exhibited a significant activity against nine laboratory control strains of bacteria and two strains of yeast Candida albicans. The tested acids were efficiently prepared by optimized phase-transfer-catalyzed (PTC) reactions of ketones with bromoform and aqueous lithium hydroxide in alcoholic solvent with triethylbenzyl ammonium chloride (TEBA) as catalyst. AB - U ovom radu je prikazano in vitro ispitivanje antimikrobnog dejstva serije α,β-nezasićenih i α-bromkarboksilnih kiselina i pokazano je da su one potencijalno dobri antimikrobni agensi. Sve kiseline 1-12 pokazale su značajnu aktivnost prema devet sojeva bakterija i dva soja gljivica Candida albicans. Ispitivane kiseline sintetisane su u optimizovanoj reakciji ketona sa bromoformom i litijum-hidroksidom u smesi rastvarača (terc-butanol/voda). Kao katalizator za prenos između faza upotrebljen je trietilbenzilamonijum-hlorid (TEBA). PB - Srpsko hemijsko društvo, Beograd T2 - Journal of the Serbian Chemical Society T1 - Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids T1 - Optimizacija sinteze i in vitro proučavanje antimikrobnog dejstva α,β-nezasićenih i α-bromkarboksilnih kiselina VL - 77 IS - 6 SP - 741 EP - 750 DO - 10.2298/JSC111104016V ER -
@article{ author = "Vitnik, Vesna and Milenković, Marina and Dilber, Sanda and Vitnik, Željko J. and Juranić, Ivan O.", year = "2012", abstract = "A series of α,β-unsaturated and α-bromo carboxylic acids were identified as potent antimicrobial agents. The antimicrobial activity was evaluated using the broth microdilution method. All acids 1-12 exhibited a significant activity against nine laboratory control strains of bacteria and two strains of yeast Candida albicans. The tested acids were efficiently prepared by optimized phase-transfer-catalyzed (PTC) reactions of ketones with bromoform and aqueous lithium hydroxide in alcoholic solvent with triethylbenzyl ammonium chloride (TEBA) as catalyst., U ovom radu je prikazano in vitro ispitivanje antimikrobnog dejstva serije α,β-nezasićenih i α-bromkarboksilnih kiselina i pokazano je da su one potencijalno dobri antimikrobni agensi. Sve kiseline 1-12 pokazale su značajnu aktivnost prema devet sojeva bakterija i dva soja gljivica Candida albicans. Ispitivane kiseline sintetisane su u optimizovanoj reakciji ketona sa bromoformom i litijum-hidroksidom u smesi rastvarača (terc-butanol/voda). Kao katalizator za prenos između faza upotrebljen je trietilbenzilamonijum-hlorid (TEBA).", publisher = "Srpsko hemijsko društvo, Beograd", journal = "Journal of the Serbian Chemical Society", title = "Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids, Optimizacija sinteze i in vitro proučavanje antimikrobnog dejstva α,β-nezasićenih i α-bromkarboksilnih kiselina", volume = "77", number = "6", pages = "741-750", doi = "10.2298/JSC111104016V" }
Vitnik, V., Milenković, M., Dilber, S., Vitnik, Ž. J.,& Juranić, I. O.. (2012). Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids. in Journal of the Serbian Chemical Society Srpsko hemijsko društvo, Beograd., 77(6), 741-750. https://doi.org/10.2298/JSC111104016V
Vitnik V, Milenković M, Dilber S, Vitnik ŽJ, Juranić IO. Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids. in Journal of the Serbian Chemical Society. 2012;77(6):741-750. doi:10.2298/JSC111104016V .
Vitnik, Vesna, Milenković, Marina, Dilber, Sanda, Vitnik, Željko J., Juranić, Ivan O., "Improved synthesis and in vitro study of antimicrobial activity of α,β-unsaturated and α-bromo carboxylic acids" in Journal of the Serbian Chemical Society, 77, no. 6 (2012):741-750, https://doi.org/10.2298/JSC111104016V . .