Synthesis and antimicrobial activity of imidazo- and pyrimido[2,1-f]-theophyllines |
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Authors: | Mosselhi A N Mosselhi Elham S Darwish Klaus Peseke |
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Institution: | (1) Department of Chemistry, Faculty of Science, Cairo University, Cairo, Egypt;(2) Department of Chemistry, Faculty of Science, Rostock University, Rostock, Germany |
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Abstract: | Heating of 8-aminotheophylline with methyl (Z)-2-benzoylamino-3-(dimethylamino)propenoate in acetic acid afforded in a one-pot synthesis a new pyrimido2,1-f]theophylline derivative. Methylation of this by using CH3I/NaH furnished in good yield the double methylated derivative. Furthermore, glycosidation of the former with 1-α-bromo-2,3,4,6-tetra-O-acetyl-d-glucose gave the β-glucoside derivative. Reaction of 8-aminotheophylline with bis(methylthio)methylene]malonitrile, ethylbis(methylthio)methylene]cyanoacetate,
1,3-diphenylprop-2-en-1-one, 2-cyano-1,3-diphenylprop-2-en-1-one, 1-(4-nitrophenyl)-3-(dimethylamino)prop-2-ennitrile, 1-phenyl-3-(dimethylamino)prop-2-en-1-one,
2-substituted 3-aryl or heteroarylprop-2-ennitrile and ethyl(arylmethylene)cyanoacetate in N,N-dimethylformamide in the presence of anhydrous potassium carbonate afforded also the corresponding new derivatives of pyrimido-2,1-f]theophylline. However, 8-aminotheophylline reacted in similar manner with 3-chloropentan-2,4-dione and 2-bromo-1-phenylethanone
to give the corresponding imidazo2,1-f]theophyllines. Furthermore, azo-coupling of one of these with 4-methylphenyldiazonium chloride was performed. The antimicrobial
activity of the products has been evaluated. The structures of all new compounds obtained were established by their spectral
analyses.
Correspondence: Mosselhi A. N. Mosselhi, Department of Chemistry, Faculty of Science, Cairo University, Cairo, Egypt. |
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Keywords: | Theophylline Fused purines Methylxanthines Glycoside Antimicrobial activity |
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