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Building Blocks for Polyamines

No.122(February 2005)
N-(2-Aminoethyl)-2-nitrobenzenesulfonamide  (1a)
N-(3-Aminopropyl)-2-nitrobenzenesulfonamide  (1b)
N-(4-Aminobutyl)-2-nitrobenzenesulfonamide  (1c)
N-(5-Aminopentyl)-2-nitrobenzenesulfonamide Hydrochloride  (1d)
N-(6-Aminohexyl)-2-nitrobenzenesulfonamide Hydrochloride  (1e)
Polyamine toxins derived from spider venom have been shown to be specific glutamate receptor blockers, known as antagonists. They are actively studied as tools for neurophysiology and as lead compounds for pharmaceutical and agrochemical agents. 1 is the diamines which possess the 2-nitrobenzenesulfonyl (Ns) group as both a protecting and activating group, and is to be ideal starting material for incorporation into a polyamine chain. For example, total synthesis of spider toxins of HO-416b (2) and Agel-489 (3) using 1 was successfully accomplised by Fukuyama and co-workers.1) In addition, the applications to the total synthesis of lipogrammistin-A, an macrocyclic polyamine using 1 are also reported.2)


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