Synthetic analogues to the spermidine-spermine alkaloid tenuilobine

Citation
K. Popaj et al., Synthetic analogues to the spermidine-spermine alkaloid tenuilobine, HELV CHIM A, 83(11), 2000, pp. 3021-3034
Citations number
36
Categorie Soggetti
Chemistry & Analysis",Chemistry
Journal title
HELVETICA CHIMICA ACTA
ISSN journal
0018019X → ACNP
Volume
83
Issue
11
Year of publication
2000
Pages
3021 - 3034
Database
ISI
SICI code
0018-019X(2000)83:11<3021:SATTSA>2.0.ZU;2-T
Abstract
Naturally occurring spider and wasp toxins are potent inhibitors of glutama te receptors in the central nervous system. They consist of a polyamine bac kbone and carboxylic acids or amino acids linked by peptide bonds. In some respects, the plant alkaloid tenuilobine, a derivative of spermine and sper midine, shows structural similarities to these toxins. In the present paper , the synthesis of the five tenuilobine analogs 12, 13, 15, 24, and 25 is d escribed. These derivatives differ in their aromatic carboxylic acid subuni ts and in the polyamine moiety.