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

Abstract

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.

• Authors: Y Nishimura, T Kudo, S Kondo, T Takeuchi, T Tsuruoka, H Fukuyasu, S Shibahara
• Journal: The Journal of antibiotics (J Antibiot (Tokyo)) Vol. 47 Issue 1 Pg. 101-7 (Jan 1994) ISSN: 0021-8820 [Print] England
• PMID: 8119851 (Publication Type: Journal Article)

Chemical References

• 6-trifluoroacetamido-4,5-dihydroxy-3-piperidinecarboxylic acid
• Acetamides
• Antineoplastic Agents
• Piperidines
• siastatin
• Glycoside Hydrolases
• Glucuronidase

Topics

• Acetamides (chemical synthesis, therapeutic use)
• Animals
• Antineoplastic Agents (chemical synthesis, therapeutic use)
• Glucuronidase (antagonists & inhibitors, metabolism)
• Glycoside Hydrolases (antagonists & inhibitors)
• Liver (drug effects, enzymology)
• Lung Neoplasms (prevention & control)
• Male
• Melanoma, Experimental (drug therapy)
• Mice
• Neoplasm Metastasis (prevention & control)
• Piperidines (chemical synthesis, therapeutic use)