Patent FR-2855172-A1 (FR)
Title: Broad-spectrum antimicrobial agents, useful e.g. as medicaments, cosmetic agents, plant protectants or preservatives, comprising new or known 3-desoxy-anthocyanidin compounds
Inventor: GEORGE FLORIAN
IPC: A61P31/04
Filed: 2003-05-21
Abstract: The use of 3-desoxy-anthocyanidins (i.e. flavylium (or 2-phenyl-1-benzopyrilium) salts) (I) as antimicrobial medicaments, as cosmetic agents, as antimicrobial agents for combating plant diseases, as preservatives or in antimicrobial materials is new. The use of 3-desoxy-anthocyanidins of formula (I) is claimed: (1) in the production of medicaments for treating microbial infections in mammals (especially humans); (2) in the production of cosmetic products; (3) for combating microbial diseases in plants; (4) for preserving perishable products (especially foods); and (5) for preparing antimicrobial materials. [Image] R 1- R 5, R 7- R 11H, halo, OH, NO 2, CN, alkoxy, acyloxy or alkyl (all of 1-12C and optionally unsaturated), a group containing at least one of Si, S and/or P; -O-glycosyl (optionally substituted (os) by alkoxy, acyloxy or alkyl (all of 1-12C and optionally unsaturated)), 2-30C alkenyl or cycloalkenyl (optionally interrupted by heteroatom(s) (specifically O, S or N and os), aryl, aralkyl, alkaryl (all of 6-30C and os), or -NY 1Y 2or -N=CY 1Y 2; Y 1, Y 2H, optionally unsaturated 1-12C alkyl, 2-30C alkenyl or cycloalkenyl (optionally interrupted by heteroatom(s) (specifically O, S or N and os), aryl, aralkyl or alkaryl (all of 6-30C and os); or Y 1+ Y 2group completing an os 4-8 (preferably 5-7) membered, aromatic or non-aromatic ring, preferably formed from C, N, O and/or S atoms; R 6H, halo, NO 2, CN, a group containing at least one of Si, S and/or P, 2-30C alkenyl, cycloalkenyl (optionally interrupted by heteroatom(s) (specifically O, S or N and os), aryl, aralkyl or alkaryl (all of 6-30C and os), or -NY' 1Y' 2, -N=CY' 1Y' 2; Y' 1, Y' 2as for Y 1, Y 2, except that Y' 1+ Y' 2cannot form a ring; two adjacent groups R 1- R 11group completing an os 4-8 (preferably 5-7) membered, aromatic or non-aromatic ring, preferably formed from C, N, O and/or S atoms; X ->anion derived from an organic or mineral acid (especially acetate, borate, citrate, tartrate, bisulfate, sulfate, phosphate, bromide, chloride, tetrafluoroborate or perchlorate) or from a sulfate or sulfonate group. in R 1-R 5, R 7-R 11the alkoxy, acyloxy or alkyl are all of 1-12C and optionally unsaturated; the group containing at least one of Si, S and/or P; -O-glycosyl is optionally substituted by alkoxy, acyloxy or alkyl (all of 1-12C and optionally unsaturated), Independent claims are included for: (a) (I) as new compounds, provided that R 3and R 10are restricted to the values given above for R 6; and (b) the preparation of the new compounds (I). ACTIVITY : Antibacterial; antifungal. 4'-Hydroxy-flavylium chloride (Ia) had minimum inhibitory concentration values of less than 3.0 Microg/ml against Staphylococcus aureus(both sensitive clinical strain IBS211 and methicillin-resistant clinical strain IBS04) and less than 60 Microg/ml against Pseudomonas aeruginosa, Candida albicans(strain IHEM 8060), Candida glabrata(patient strain) and Aspergillus fumigatus(strain GASP 4707). MECHANISM OF ACTION : None given in the source material.