Analogs of N-isoprenylagmatine have been synthesized either in soln. or on solid support. These compds. showed moderate to potent activity against NOS-II and M-PAO, with good selectivity with respect to NOS-I and B-PAO, resp. In particular, compd. 2 proved to be as potent as Guazatine, the most potent M-PAO inhibitor reported so far. Polyamine oxidases (PAOs) are flavoproteins which oxidize polyamines at the secondary amino group, giving different reaction products, depending on the source of the enzyme. Animal PAOs transform N1-acetyl derivs. of spermidine and spermine into putrescine and spermidine, resp., plus acetamidopropanal and H2O2, thus participating in the interconversion metab. of polyamines (Figure 1). Conversely, plant and bacterial PAOs oxidize spermidine and spermine to the corresponding aminoaldehyde, diaminopropane and H2O2.
Solution and solid-phase synthesis of aminoalkylguanidines inhibiting polyamine oxidase and nitric oxid synthase
SCHENONE, SILVIA;
2002-01-01
Abstract
Analogs of N-isoprenylagmatine have been synthesized either in soln. or on solid support. These compds. showed moderate to potent activity against NOS-II and M-PAO, with good selectivity with respect to NOS-I and B-PAO, resp. In particular, compd. 2 proved to be as potent as Guazatine, the most potent M-PAO inhibitor reported so far. Polyamine oxidases (PAOs) are flavoproteins which oxidize polyamines at the secondary amino group, giving different reaction products, depending on the source of the enzyme. Animal PAOs transform N1-acetyl derivs. of spermidine and spermine into putrescine and spermidine, resp., plus acetamidopropanal and H2O2, thus participating in the interconversion metab. of polyamines (Figure 1). Conversely, plant and bacterial PAOs oxidize spermidine and spermine to the corresponding aminoaldehyde, diaminopropane and H2O2.
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