Synthesis of quaternary ammonium bromides of 5-[4-(?-dialkylaminoalkoxy)phenyl-methylene]-1, 3, 3-trimethyl-2-oxabicyclo [2.2.2]octan-6-ones as potential UV sunscreens
| Autor: | Alberto Bargagna, P. Schenone, Emilia Mariani, S. Dorato, Mario Longobardi |
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| Rok vydání: | 1994 |
| Předmět: |
Aging
Uv absorption Pharmaceutical Science Ether Dermatology Medicinal chemistry Benzalkonium chloride chemistry.chemical_compound Colloid and Surface Chemistry chemistry Chemistry (miscellaneous) Biological property Drug Discovery medicine Organic chemistry Ammonium Methylene Enone Reference standards medicine.drug |
| Zdroj: | International Journal of Cosmetic Science. 16:171-180 |
| ISSN: | 1468-2494 0142-5463 |
| DOI: | 10.1111/j.1467-2494.1994.tb00095.x |
| Popis: | Synopsis Materials and methods for the synthesis of eight quaternary ammonium bromides of 5-[4-(ω-dialkylaminoalkoxy)phenylmethylene]-1,3,-trimethyl-2-oxabicyclo[2.2.2]octan-6-ones are illustrated. They were routinely prepared starting from cineole aminoethers by reaction with primary alkyl bromides and their physico-chemical data are reported. These substances have been tested for UV filtering and/or microbiological activity. The substances have their UV absorption maxima at 315–322 nm. Tests on antimicrobial activity were performed using benzalkonium chloride as reference standard. All quaternary ammonium bromides were totally inactive against Escherichia coli (Gram —) and partially active on Staphylococcus aureus (Gram +). These preliminary findings seem to indicate that these new quaternary ammonium bromides could be considered as potential UV sunscreens. Resume Les methodes et le materiel de synthese de huit bromures d'ammoniums quaternaires de 5-[4-(ω-dialkyl-aminoalkoxy)phenylmethylene]-1, 3,3-trimethyl-2-oxabicyclo[2.2.2]octan-6-ones sont ici decrits. Ils ont ete prepares classiquement a partir d'aminoethers de cineol, par reaction avec des bromures d'alkyles primaires. Leurs caracteristiques physico-chimiques sont decrites. Le pouvoir filtrant vis-a-vis des UV et/ou l'activite microbiologique de ces substances ont ete testes. Ces composes ont leur pic d'absorption maximum entre 315 et 322 nm. Les tests d'activite antimicrobienne ont ete realises en utilisant le chlorure de benzalkonium comme reference. Tous ces bromures d'ammoniums quaternaires se sont reveles totalement inactifs vis-a-vis d'Escherichia coli (Gram —), et partiellement actifs vis-a-vis de Staphylococcus aureus (Gram +). Ces resultats preliminaires semblent indiquer que ces nouveaux bromures d'ammoniums quaternaires pourraient etre des ecrans solaires anti-UV potentials. |
| Databáze: | OpenAIRE |
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