Reaction of pyrylium salts with nucleophiles. 23: triarylethene derivatives containing an oxyalkyleneamino or oxyalkylene-N-pyridinium side chain.
A synthetic design was devised for preparing primary amines related to anticancer drugs clomiphene and tamoxifen on the basis of key intermediates with a phenolic group, to which a side chain (omega-aminoethoxy or omega-aminopropoxy) was attached. These compounds were then reacted with 2,4,6-trimethyl- or 2,4,6-triphenylpyrylium salts. This afforded pyridinium analogues of clomiphene and tamoxifen as potential therapeutic agents for treatment against hormone-dependent tumors.
Stanciuc
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Oncological Institute, Bucharest, Roumania.
Balaban
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D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002996:Clomiphene / Q000031:analogs & derivatives; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D009376:Neoplasms, Hormone-Dependent / Q000188:drug therapy; D011714:Pyrans / Q000138:chemical synthesis* / Q000494:pharmacology; D011726:Pyridinium Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D013629:Tamoxifen / Q000031:analogs & derivatives; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D011714:Pyrans; D011726:Pyridinium Compounds; D013629:Tamoxifen; D002996:Clomiphene