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Totally syntheticanalogues of siastatin B. III. Trifluoroacetamide analogues having inhibitory activity for tumor metastasis.

1994; Springer Nature; Volume: 47; Issue: 1 Linguagem: Inglês

10.7164/antibiotics.47.101

1881-1469

Yoshio Nishimura, Toshiaki Kudo, Shinichi Kondo, TOMIO TAKEUCHI, Tsutomu Tsuruoka, HARUMI FUKUYASU, SEUI SHIBAHARA,

Synthesis and biological activity

A trifluoroacetamide analogue of siastatin B, (3S,4S,5R,6R)-6-(trifluoroacetamido)-4,5-dihydroxy-3-piperidine carboxylic acid has been chemically synthesized. This compound, as well as the previously synthesized analogue, (3R,4R,5R,6R)-6-(trifluoroacetamido)-3,4,5-trihydroxy-3-piperid inecarboxylic acid, showed marked inhibitory activity against beta-glucuronidase and significant inhibition of experimental pulmonary metastasis of the highly metastatic melanoma B16.