Title compds. [I; A = (cyclo)alkyl, cyanoalkyl, cycloalkylalkyl, (substituted) phenylalkyl, (unsatd.) lactone moiety, acylalkyl, carbamoylalkyl, etc.; A1 = H, Cl; R, R1 = H, (cyclo)alkyl, cyanoalkyl, alkylcarbonyloxyalkyl, (substituted) phenylalkyl, etc.; Y = OH, haloalkoxy, hydroxyalkoxy, alkyl, (substituted) phenylalkyl, acylalkyl, carbamoylalkyl, amino; B = H, N-acetyl-β-D-2-deoxy-2-aminoglucopyranosyl; M = H, α-D-mannopyranosyl], were prepd. as antibacterials. Thus, PhCH2O2CCl in acetone was added to a soln. of antibiotic L 17392 and Et3N in DMF and the mixt. was stirred 2 h to give ∼94% N15-carbobenzyloxydeglucoteicoplanin. The latter was converted to the Me ester with MeI/KHCO3 in DMF. The ester was alkylated with 1-bromo-2,3-epoxypropane/K2CO3 in ME2SO and the product was hydrogenated over Pd/BaSO4 to give I (R, R1 = H, A = 2,3-epoxypropyl, A1 = Cl, B, M = H, Y = MeO). The latter had min. inhibitory concns. of 0.125, 1, and 0.063 μM against Staphylococcus aureus Tour L165, S. haemolyticus L602, and S. epidermis ATCC 12228, resp.

Preparation of 56-O-alkyl derivatives of aglycones and pseudoaglycones of teicoplanin as antibacterials / A. Trani, P. Ferrari, P. Seneci, R. Ciabatti.

Preparation of 56-O-alkyl derivatives of aglycones and pseudoaglycones of teicoplanin as antibacterials

P. Seneci
Penultimo
;
1990

Abstract

Title compds. [I; A = (cyclo)alkyl, cyanoalkyl, cycloalkylalkyl, (substituted) phenylalkyl, (unsatd.) lactone moiety, acylalkyl, carbamoylalkyl, etc.; A1 = H, Cl; R, R1 = H, (cyclo)alkyl, cyanoalkyl, alkylcarbonyloxyalkyl, (substituted) phenylalkyl, etc.; Y = OH, haloalkoxy, hydroxyalkoxy, alkyl, (substituted) phenylalkyl, acylalkyl, carbamoylalkyl, amino; B = H, N-acetyl-β-D-2-deoxy-2-aminoglucopyranosyl; M = H, α-D-mannopyranosyl], were prepd. as antibacterials. Thus, PhCH2O2CCl in acetone was added to a soln. of antibiotic L 17392 and Et3N in DMF and the mixt. was stirred 2 h to give ∼94% N15-carbobenzyloxydeglucoteicoplanin. The latter was converted to the Me ester with MeI/KHCO3 in DMF. The ester was alkylated with 1-bromo-2,3-epoxypropane/K2CO3 in ME2SO and the product was hydrogenated over Pd/BaSO4 to give I (R, R1 = H, A = 2,3-epoxypropyl, A1 = Cl, B, M = H, Y = MeO). The latter had min. inhibitory concns. of 0.125, 1, and 0.063 μM against Staphylococcus aureus Tour L165, S. haemolyticus L602, and S. epidermis ATCC 12228, resp.
Gruppo Lepetit S.p.A., Italy
C07K009-00
EP 391077
glycopeptides ; natural products ; antibacterials
Settore CHIM/06 - Chimica Organica
Settore CHIM/11 - Chimica e Biotecnologia delle Fermentazioni
Preparation of 56-O-alkyl derivatives of aglycones and pseudoaglycones of teicoplanin as antibacterials / A. Trani, P. Ferrari, P. Seneci, R. Ciabatti.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/186965
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