1-(pakeistų fenil)dihidro-2,4 (1H,3H)pirimidindionų, jų 2-tioanalogų sintezė, deciklizacija ir biologinės savybės

Abstract

Kondensuojant N-pakeistus fenil-b-alaninus su karbamidu ar kalio tiocianatu acto rūgštyje susintetinti atitinkami N-karbamoil- ir N-tiokarbamoil-b-alaninai, kurie, be išskyrimo iš reakcijos mišinių, druskos rūgštimi ciklizuoti į 1-pakeistus dihidro-2,4(1H,3H)pirimidindionus bei dihidro-4(1H,3H)pirimidinon-2-tionus. Individualūs N-pakeisti fenil-N-karbamoil-b-alaninai susintetinti iš atitinkamų 1-pakeistų dihidro-2,4(1H,3H)pirimidindionų hidrolizuojant juos šarminėje terpėje, o po to parūgštinant tirpalus acto rūgštimi. Ištirtas N-pakeistų fenil-N-karbamoil-b-alaninų natrio druskų poveikis miežių grūdų augimui bei sėmeniniams linams in vitro

Dihydropyrimidinediones and their 2-thioanalogues were synthesized by condensation N-substituted phenyl-β-alanines with urea or potassium thiocyanates in acidic conditions. The synthesized heterocycles are acid-resistant, but in basic medium they easily cleave forming the respective salts of N-substituted phenyl-N-carbamoyl- and N-substituted phenyl-N-thiocarbamoyl-β-alanines. Derivatives of N-substituted phenyl-β-alanine, N-substituted phenyl-N-carbamoyl-β-alanines in the form of soluble sodium salts were investigated. The biological activity of N-substituted phenyl-N-carbamoyl-β-alanine derivatives was studied by the method of laboratory screening at the Laboratory of Genetics and Biotechnology, Lithuanian University of Agriculture. ‘Aura’ barley seeds were moistened with 0.09 g/l solutions of N-substituted phenyl-N-carbamoyl-β-alanine derivatives and germinated on filter paper in Petri dishes. The barley seedlings were scored for physiological response (growth intensity, root systems, average biomass of 10 seedlings). The results showed that N-carbamoyl-N-(2-methoxy-5-nitrophenyl)-β-alanine sodium salt stimulated the growth of roots and shoots of barley seedlings. In this variant of barley, roots were by 33.7% longer and shoots by 42.2% higher, and the biomass was higher by 8% in comparison with the control sample. N-carbamoyl-N-(2-methoxy-5-nitrophenyl)-β-alanine sodium salt was selected to study the morphogenesis and callus induction of oilseed flax in vitro. The results of the investigation have revealed that N-carbamoyl-N-(2-methoxy-5-nitrophenyl)-β-alanine sodium salt in the nutrition MS medium at a concentration of 8.8 μM stimulated oilseed flax callus organogenesis in vitro. N-carbamoyl-N-(2-methoxy-5-nitrophenyl)-β-alanine sodium in the nutrition medium at concentration of 2.2 μM increased callus induction by 33.6% in comparison with the control plants