SYNTHESIS AND CYTOTOXIC ACTIVITY OF 4-SUBSTITUTED 3-CYANO-6,6-DIMETHYL-5,6-DIHYDRO-2-PYRANONES

Authors

  • L. Leite Latvian Institute of Organic Synthesis, Riga LV 1006
  • D. Jansone Latvian Institute of Organic Synthesis, Riga LV 1006
  • M. Fleisher Latvian Institute of Organic Synthesis, Riga LV 1006
  • H. Kazhoka Latvian Institute of Organic Synthesis, Riga LV 1006
  • J. Popelis Latvian Institute of Organic Synthesis, Riga LV 1006
  • N. Veretennikova Latvian Institute of Organic Synthesis, Riga LV 1006
  • I. Shestakova Latvian Institute of Organic Synthesis, Riga LV 1006
  • I. Domracheva Latvian Institute of Organic Synthesis, Riga LV 1006
  • E. Lukevics Latvian Institute of Organic Synthesis, Riga LV 1006

Keywords:

benzaldehyde, substituted δ-lactones, crotonic condensation mechanism, semiempirical AM1 method, cytotoxic activity, OREX expert system

Abstract

The respective 4-(arylvinyl)lactones and compounds of the Michael adduct type were synthesized by the condensation of substituted benzaldehydes with 3-cyano-4,6,6-trimethyl-5,6-dihydro-2-pyranone in the presence of catalytic amounts of sodium hydroxide. It was shown by the semiempirical AM1 method that the indicated products can be formed through one and the same intermediate compound. Some of the synthesized phenylvinyl-5,6-dihydro-2-pyranones have a cytotoxic effect, and this corresponds to the prognosis of the OREX expert system.

How to Cite
Leite, L.; Jansone, D.; Fleisher, M.; Kazhoka, H.; Popelis, J.; Veretennikova, N.; Shestakova, I.; Domracheva, I.; Lukevics, E. Chem. Heterocycl. Compd. 2004, 40, 715. [Khim. Geterotsikl. Soedin. 2004, 839.]

For this article in the English edition, see DOI 10.1023/B:COHC.0000040766.10102.81

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Published

2004-06-25

Issue

No. 6 (2004)

Section

Original Papers