The present invention provides new glucide derivs. of formula I or II, in which R1 is the acyl of a carboxylic acid of formula RCOOH, in which R is selected from the group consisting of linear or branched, satd. or unsatd. alkyl which has from 1 to 6 carbon atoms and which is optionally substituted by one or more aryl radicals or by one or more cycloalkyl radicals having from 3 to 6 carbon atoms, satd. or unsatd. cycloalkyl having from 3 to 6 carbon atoms, and aryl or heteroaryl optionally substituted by one or more substituents selected from alkoxy groups having from 1 to 3 carbon atoms, halogen atoms and aryl groups; X is -NR6; R2-R6 are selected, independently of one another, from the group consisting of hydrogen, cyclic or acyclic, satd. or unsatd., branched or unbranched alkyl having from 1 to 8 carbon atoms, and cyclic or acyclic, satd. or unsatd., branched or unbranched acyl having from 1 to 8 carbon atoms, having a biol. activity as inducers of erythroid cell differentiation, constituted by an acyl moiety linked to a 3-deoxyglucide unit through an amine group. The presence of a stable covalent bond between the acyl moiety and the 3-deoxyglucide moiety of the mol. enables rapid enzymic hydrolysis of these derivs. to be avoided. Thus glycoside III was prepd. as inducers of erythroid cell differentiation. The results in which the level of erythroid differentiation (expressed as a percentage of the K562 human cells which were pos. to benzidine with respect to the total cells) was evaluated (32-85% of K562 cells pos. to benzidine).
Preparation of 3-deoxy-3-amide glycosides as inducers of erythroid differentiation
CATELANI, GIORGIO;D'ANDREA, FELICIA;
2003-01-01
Abstract
The present invention provides new glucide derivs. of formula I or II, in which R1 is the acyl of a carboxylic acid of formula RCOOH, in which R is selected from the group consisting of linear or branched, satd. or unsatd. alkyl which has from 1 to 6 carbon atoms and which is optionally substituted by one or more aryl radicals or by one or more cycloalkyl radicals having from 3 to 6 carbon atoms, satd. or unsatd. cycloalkyl having from 3 to 6 carbon atoms, and aryl or heteroaryl optionally substituted by one or more substituents selected from alkoxy groups having from 1 to 3 carbon atoms, halogen atoms and aryl groups; X is -NR6; R2-R6 are selected, independently of one another, from the group consisting of hydrogen, cyclic or acyclic, satd. or unsatd., branched or unbranched alkyl having from 1 to 8 carbon atoms, and cyclic or acyclic, satd. or unsatd., branched or unbranched acyl having from 1 to 8 carbon atoms, having a biol. activity as inducers of erythroid cell differentiation, constituted by an acyl moiety linked to a 3-deoxyglucide unit through an amine group. The presence of a stable covalent bond between the acyl moiety and the 3-deoxyglucide moiety of the mol. enables rapid enzymic hydrolysis of these derivs. to be avoided. Thus glycoside III was prepd. as inducers of erythroid cell differentiation. The results in which the level of erythroid differentiation (expressed as a percentage of the K562 human cells which were pos. to benzidine with respect to the total cells) was evaluated (32-85% of K562 cells pos. to benzidine).I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
