Application

No.122
Building Blocks for Polyamines
A1627 N-(2-Aminoethyl)-2-nitrobenzenesulfonamide (1a) 1g
A1628 N-(3-Aminopropyl)-2-nitrobenzenesulfonamide (1b) 1g
A1630 N-(4-Aminobutyl)-2-nitrobenzenesulfonamide (1c) 1g
A1661 N-(5-Aminopentyl)-2-nitrobenzenesulfonamide Hydrochloride (1d) 1g
A1662 N-(6-Aminohexyl)-2-nitrobenzenesulfonamide Hydrochloride (1e) 1g

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)

References

1) Total synthesis of polyamine toxin HO-416b and Agel-489
a)Y. Hidai, T. Kan, T. Fukuyama, Tetrahedron Lett., 40, 4711 (1999).
b)Y. Hidai, T. Kan, T. Fukuyama, Chem. Pharm. Bull., 48, 1570 (2000).
2) Total synthesis of lipogrammistin-A
T. Kan, A. Fujiwara, H. Kobayashi, T. Fukuyama, Tetrahedron, 58, 6267
(2002).

Related Compounds

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A1371 N-Boc-1,2-diaminoethane 5g
1g
A1372 N-Boc-1,3-propanediamine 5g
1g
A1373 N-Boc-1,4-diaminobutane 5g
1g
A1374 N-Boc-1,5-diaminopentane 5g
1g
A1375 N-Boc-1,6-hexanediamine 5g
1g
C1511 N-Cbz-1,2-diaminoethane Hydrochloride 5g
1g
C1512 N-Cbz-1,3-diaminopropane Hydrochloride 5g
1g
C1519 N-Cbz-1,4-diaminobutane Hydrochloride 5g
1g
C1520 N-Cbz-1,5-diaminopentane Hydrochloride 5g
1g
C1521 N-Cbz-1,6-diaminohexane Hydrochloride 5g
1g
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