Synthesis and biological activity of naphthalene analogues of phenstatins: naphthylphenstatins.
Novel phenstatin analogues with a 2-naphthyl moiety combined with either a 2,3,4- or a 3,4,5-trimethoxyphenyl ring have been synthesized, and their tubulin polymerization inhibiting and cytotoxic activities have been evaluated. The 2-naphthyl ring is a better replacement for the 3-hydroxy-4-methoxyphenyl ring in the phenstatin series than in the combretastatin series. For the naphthylphenstatins, the carbonyl is required, and the preferred orientation of the trimethoxyphenyl ring is the one found in combretastatins.
Alvarez
Concepción
C
Departament de Química Farmacéutica, Facultad de Farmacia, Universidad de Salamanca, Campus Miguel de Unamuno, 37007 Salamanca, Spain.
Alvarez
Raquel
R
Corchete
Purificación
P
Pérez-Melero
Concepción
C
Peláez
Rafael
R
Medarde
Manuel
M
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D001632:Bibenzyls / Q000737:chemistry / Q000494:pharmacology; D006367:HeLa Cells; D006801:Humans; D020128:Inhibitory Concentration 50; D008956:Models, Chemical; D009281:Naphthalenes / Q000138:chemical synthesis / Q000494:pharmacology*; D013237:Stereoisomerism; D013267:Stilbenes / Q000737:chemistry / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014404:Tubulin / Q000737:chemistry / Q000494:pharmacology; D050257:Tubulin Modulators / Q000138:chemical synthesis / Q000494:pharmacology*; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D001632:Bibenzyls; D009281:Naphthalenes; D013267:Stilbenes; D014404:Tubulin; D050257:Tubulin Modulators; C040105:combretastatin