Studies On The Synthesis And Antibacterial Activity Of Pyrrole-pyrimidone Compounds

Alkaloids containing pyrrole group exist widely in Marine natural products, and exhibit a wide range of biological activity. Pyrrole alkaloids obtained by synthesis method has important significance, it is beneficial to protect marine resources and develop marine drugs. In this thesis,32compounds were designed and synthesized by Biginelli reaction, applied the method of solution-free multi-component. And the32compounds were first reported. The structures of synthetic compounds were verified and characterized by TLC,1HNMR, IR and LC-MS. By way of bacteriostatic experiment, the antibacterial activity of the32compounds was evaluated preliminary. This thesis was summarized as follows:In chapter1, marine pyrrole alkaloids are introduced firstly, and then research status, development and activity of pyrrole and pyrimidine are elaborated. Furthermore, Green synthesis, Multi-component reactions and Target-oriented synthesis were discussed. On these bases, we proposed the task of thesis and the purpose of study.In chapter2, according to literature, the intermediates A1-A5were synthesized by knorr reaction. The derivatives of pyrrole B1-B5were obtained by using compounds Al-A5as material, THF-HAc-H2O as solvent and ceric ammonium nitrate (CAN) as oxidizer. And then the properties and synthesis conditions of compounds B1-B5were studied and investigated.In chapter3, sixteen oxo-pyrrole-dihydropyrimidine-ones and sixteen thio-pyrrole-dihydropyrimidine-ones were synthesized efficiently by a solvent-free and multi-component Biginelli’s condensation of compounds B1-B5, urea (thiourea) and ethyl acetoacetate (methyl acetoacetate, acetylacetone or Benzoylacetone) with the catalysis of phosphoric acid. Then the properties and synthesis conditions of the compounds were detected.In chapter4, the antibacterial activity of target product was evaluated. Vibrio alginolyticus, vibrio parahaemolyticus, bacillus subtilis, streptococcus faecalis. pseudomonas aeruoginosa, pseudomonas fluorescent pseudomonas, fusarium oxysporum, geotrichum candidum, and yeast strains were selected as the research objects. The practical results show that the32compounds have no antimicrobial activity nearly.