ABSTRACT
A number of important fused heterocyclic systems have been prepared by the reaction of 4-((3,5-diamino-1H-pyrazol-4-yl)-diazenyl)-N-(thiazol-2-yl)-benzenesulfonamide with some bifunctional nucleophiles such as ethyl acetoacetate, acetylacetone or arylidenemalonononitrile derivatives to obtain pyrazolo[1,5-a]pyrimidine derivatives. The structures of the newly synthesized compounds were determined based on their IR, 1H and 13C NMR and mass spectroscopic data. Most of the compounds produced showed good antibacterial and antifungal activity.
Subject(s)
Anti-Bacterial Agents/pharmacology , Antifungal Agents/pharmacology , Pyrazoles/pharmacology , Pyrimidines/pharmacology , Sulfathiazoles/pharmacology , Triazines/pharmacology , Anti-Bacterial Agents/chemical synthesis , Antifungal Agents/chemical synthesis , Bacteria/drug effects , Candida albicans/drug effects , Fusarium/drug effects , Microbial Sensitivity Tests , Molecular Structure , Pyrazoles/chemical synthesis , Pyrimidines/chemical synthesis , Structure-Activity Relationship , Sulfathiazoles/chemical synthesis , Triazines/chemical synthesisABSTRACT
Synthesis of some novel tricyclic compounds bearing thienodipyrimidine moiety by the reaction of ethyl 6-amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydrothieno[3,2-d]pyrimidine-7-carboxylate (1) with different types of aromatic amines to give the corresponding carboxamide derivatives 2-11, which cyclized with triethyl orthoformate in acetic anhydride to afford thieno[2,3-d:4,5-d']dipyrimidine derivatives 12-15 is described. Similarly, thieno[2,3-d:4,5-d']dipyrimidine derivative 17 was also prepared via the reaction of carboxamide derivative 2 with chloroacetyl chloride in chloroform to give thieno[3,2-d]pyrimidine-7-carboxamide derivative 16, followed by a cyclization in boiling acetic anhydride. The structure of these compounds was confirmed on the basis of their spectral and analytical data such as IR, 1H-NMR, 13C-NMR spectroscopy and mass spectral data. The synthesized compounds were screened for their cytotoxic activity.