Title compds. [I; R1 = H, alkyl, dialkylaminoalkylene; X = alkylene, alkylenecarbonyl; R2 = amino, 5-6 membered N-heterocyclyl; R1R2 = atoms to form a (substituted) 5-6 membered heterocyclic ring; W1 = Ph; W2 = OH; or W1, W2 both = Me; X1 = H, Me; X2 = H, Me, MeOCH2; when both W1, W2 = Me, then X1 = Me and X2 = H], were prepd. Thus, GE2270 factor A3 was condensed with H-Ser-Pro-NHCH2CH2NEt2 hydrochloride (prepn. given) using Et3N/DPPA in DMF and the condensation product in THF was treated with Burgess reagent in CH2Cl2 followed by Me2CHOH quench and reflux to give I; (R1 = H; XR2 = CH2CH2NEt2; W1 = Ph; W2 = OH; X1 = Me; X2 = MeOCH2). The latter showed a min. inhibitory concn. of 0.06 μg/mL against Staphylococcus aureus.

Preparation of basic prolineamide derivatives of GE2270 and GE2270-like antibiotics / S. Lociuro, P. Seneci, E. Restelli, R. Ciabatti.

Preparation of basic prolineamide derivatives of GE2270 and GE2270-like antibiotics

P. Seneci
Secondo
;
1996

Abstract

Title compds. [I; R1 = H, alkyl, dialkylaminoalkylene; X = alkylene, alkylenecarbonyl; R2 = amino, 5-6 membered N-heterocyclyl; R1R2 = atoms to form a (substituted) 5-6 membered heterocyclic ring; W1 = Ph; W2 = OH; or W1, W2 both = Me; X1 = H, Me; X2 = H, Me, MeOCH2; when both W1, W2 = Me, then X1 = Me and X2 = H], were prepd. Thus, GE2270 factor A3 was condensed with H-Ser-Pro-NHCH2CH2NEt2 hydrochloride (prepn. given) using Et3N/DPPA in DMF and the condensation product in THF was treated with Burgess reagent in CH2Cl2 followed by Me2CHOH quench and reflux to give I; (R1 = H; XR2 = CH2CH2NEt2; W1 = Ph; W2 = OH; X1 = Me; X2 = MeOCH2). The latter showed a min. inhibitory concn. of 0.06 μg/mL against Staphylococcus aureus.
Gruppo Lepetit S.P.A., Italy
C07K005-06
WO 9624607
Settore CHIM/06 - Chimica Organica
Settore CHIM/11 - Chimica e Biotecnologia delle Fermentazioni
Preparation of basic prolineamide derivatives of GE2270 and GE2270-like antibiotics / S. Lociuro, P. Seneci, E. Restelli, R. Ciabatti.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/2434/186948
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