Abstract
BackgroundIsoxazoles exhibit interesting biological activities, and the 1,3-dipolar cycloaddition(13DC) reactions play an important role in both mechanistic and synthetic organic chemistry. Pyrazoles and annulated pyrazoles exhibit some diverse biological activities. They are used as antipyretic, analgesic drugs, tranquilizing, and herbicidal agents. Pyrazoles are also used extensively as useful synthons in organic synthesis. Pyrazolo[3,4-d]pyridazines showed good antimicrobial, anti-inflammatory and analgesic activities. Several oximes are found to be hyperglycemic, anti-neoplastic, anti-inflammatory, anti-leishmanial and VEGFR-2 kinase inhibitors.ResultsThe present work describes an efficient synthesis protocol and molecular orbital calculations of isoxazoline and pyrrolo[3,4-d]isoxazole-4,6-dione derivatives from the reaction of hydroximoyl chloride with acrylonitrile, acrylamide, and N-arylmalemides. In addition, pyrazoles and pyrazolo[3,4-d]pyridazines are obtained via the reaction of 3-(dimethylamino)-1-(2,4-dimethyl-1,3-thiazol-5-yl)prop-2-ene-1-one with hydrazonoyl halides. Pyrazolo[1,5-a]pyrimidines were derived from condensation of either Sodium Salt of 3-Hydroxy-1-(2,4-dimethylthiazol-5-yl)prop-2-en-1-one (10) or 3-(dimethylamino)-1-(2,4-dimethyl)(1,3-thiazol-5-yl)prop-2-en-1-one (11) with aiminopyrozoles. A comparative study of the biological activity of the synthesized compounds with ampicillin and tetracycline is compiled in Table 3. Generally, all synthesized compounds showed an adequate inhibitory efficiency of growth of gram-positive and gram-negative bacteria. Structures of the newly synthesized compounds were elucidated by elemental analysis, spectral data and a computational study.ConclusionsIn summary, new and efficient synthetic routes of isoxazoline, pyrrolo[3,4-d]isoxazole-4,6-dione derivatives, pyrazoles, pyrazolo[3,4-d]pyridazines and pyrazolo[1,5-a]pyrimidines have been achieved and the biological activity has been investigated.Graphical abstractNew and efficient synthetic routes of isoxazoline, pyrrolo[3,4-d]isoxazole-4,6-dione derivatives, pyrazolo[3,4-d]pyridazines and pyrazolo [1,5-a] pyrimidines
Highlights
Isoxazoles exhibit interesting biological activities, and the 1,3-dipolar cycloaddition(13DC) reactions play an important role in both mechanistic and synthetic organic chemistry
The synthesis of biologically active compounds based on pyrazolo[3,4d]pyridazines systems are of outstanding importance for medicinal and biological utilities [18, 19], Generally, pyrazolo[3,4-d]pyridazines showed good antimicrobial, anti-inflammatory and analgesic activities [20]
In summary, new and efficient synthetic routes of isoxazoline, pyrrolo[3,4-d]isoxazole-4,6-dione derivatives, pyrazoles, pyrazolo[3,4-d]pyridazines and pyrazolo [1,5-a] pyrimidines have been achieved, and computational investigations are in complete agreement with experimental
Summary
Isoxazoles exhibit interesting biological activities, and the 1,3-dipolar cycloaddition(13DC) reactions play an important role in both mechanistic and synthetic organic chemistry. Pyrazoles and annulated pyrazoles exhibit some diverse biological activities. They are used as antipyretic, analgesic drugs, tranquilizing, and herbicidal agents. Pyrazolo[3,4-d]pyridazines showed good antimicrobial, anti-inflammatory and analgesic activities. Zaki et al Chemistry Central Journal (2016) 10:17 analgesic drugs [5–7], tranquilizing [8] and herbicidal [9] agents. The synthesis of biologically active compounds based on pyrazolo[3,4d]pyridazines systems are of outstanding importance for medicinal and biological utilities [18, 19], Generally, pyrazolo[3,4-d]pyridazines showed good antimicrobial, anti-inflammatory and analgesic activities [20]. We report a facile synthesis procedure for some new derivatives of the newly developed isoxazoline, pyrrolo[3,4-d] isoxazole-4,6-dione derivatives, pyrazoles, pyrazolo[3,4-d] pyridazines and pyrazolo[1,5-a] pyrimidines
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