Synthesis and cytostatic properties of monoterpene derivatives of cyanuric and isocyanuric acids

Acta Pol Pharm. 2004 Dec:61 Suppl:29-32.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antineoplastic Agents / chemical synthesis*
  • Antineoplastic Agents / pharmacology*
  • Cell Line, Tumor
  • Drug Screening Assays, Antitumor
  • Humans
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Monoterpenes / chemical synthesis*
  • Monoterpenes / pharmacology*
  • Spectrophotometry, Infrared
  • Triazines / chemical synthesis*
  • Triazines / pharmacology*

Substances

  • Antineoplastic Agents
  • Indicators and Reagents
  • Monoterpenes
  • Triazines
  • cyanuric acid