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Spermidine, spermine and other polyamines 1-5 were selectively protected at the terminal primary amino functions without affecting the secondary amino groups using N-ethoxycarbonyl-phthalimide (15), the Nefkens’ reagent. Three representative products, 17, 18 and 20, readily underwent acylation at the secondary amino nitrogen to give the corresponding compounds 21-26. Selective deprotection of two representative samples 22 and 25 at the primary amino function by hydrazinolysis yielded the corresponding derivatives 27 and 28 with free primary amino groups.

In the Search for New Anticancer Drugs, XVI Selective Protection and Deprotection of Primary Amino Groups in Spermine, Spermidine and Other Polyamines