Totally synthetic analogues of siastatin B. III. Trifluoroacetamide analogues having inhibitory activity for tumor metastasis.
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.
Nishimura
Y
Y
Institute of Microbial Chemistry, Tokyo, Japan.
Kudo
T
T
Kondo
S
S
Takeuchi
T
T
Tsuruoka
T
T
Fukuyasu
H
H
Shibahara
S
S
D000081:Acetamides / Q000138:chemical synthesis* / Q000627:therapeutic use*; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000627:therapeutic use*; D005966:Glucuronidase / Q000037:antagonists & inhibitors* / Q000378:metabolism; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors; D008099:Liver / Q000187:drug effects / Q000201:enzymology; D008175:Lung Neoplasms / Q000517:prevention & control; D008297:Male; D008546:Melanoma, Experimental / Q000188:drug therapy*; D051379:Mice; D009362:Neoplasm Metastasis / Q000517:prevention & control; D010880:Piperidines / Q000138:chemical synthesis* / Q000627:therapeutic use*
C086155:6-trifluoroacetamido-4,5-dihydroxy-3-piperidinecarboxylic acid; D000081:Acetamides; D000970:Antineoplastic Agents; D010880:Piperidines; C011353:siastatin; D006026:Glycoside Hydrolases; D005966:Glucuronidase