Synthesis and cytostatic properties of monoterpene derivatives of cyanuric and isocyanuric acids.
Symmetric, trisubstituted derivatives of cyanuric and isocyanuric acid 3a-e and 4a-e, respectively have been prepared by treatment of cyanuric chloride 1 with appropriate terpenic alcohols 2a-e. Under less basic conditions involving treatment of appropriate alcohols 2a-e with metallic sodium, less polar cyanuric acid derivatives 3a-e were obtained in 74-85 yield. Under more basic conditions, in the presence of sodium hydride, isocyanuric acid derivatives 4a-e were prepared in 71-88 yield. Cytostatic activity of (IR,2S,5R)-menthol derivative (3a) has been evaluated on 9 cancer subtypes including 62 tumor cell lines. The studies have shown that contrary to expectations, 2,4,6-trimentoloxy-1,3,5-triazine revealed a weak or moderate activity against most of the cell lines.
Kamiński
Z J
ZJ
Institute of Organic Chemistry, Technical University of Lódź, 116 Zeromskiego Str., 90-924 Lódź. kaminsz@mail.p.lodz.pl
Kolesińska
B
B
Markowicz
S W
SW
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D039821:Monoterpenes / Q000138:chemical synthesis* / Q000494:pharmacology*; D013055:Spectrophotometry, Infrared; D014227:Triazines / Q000138:chemical synthesis* / Q000494:pharmacology*
D000970:Antineoplastic Agents; D007202:Indicators and Reagents; D039821:Monoterpenes; D014227:Triazines; C004632:cyanuric acid