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Synthesis and antimicrobial activity of imidazo- and pyrimido[2,1-f]-theophyllines

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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 pyrimido[2,1-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, ethyl[bis(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 imidazo[2,1-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.

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Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Cairo University, Cairo, Egypt

    Mosselhi A. N. Mosselhi & Elham S. Darwish

  2. Department of Chemistry, Faculty of Science, Rostock University, Rostock, Germany

    Klaus Peseke

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  1. Mosselhi A. N. Mosselhi
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  2. Elham S. Darwish
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  3. Klaus Peseke
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Correspondence to Mosselhi A. N. Mosselhi.

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Correspondence: Mosselhi A. N. Mosselhi, Department of Chemistry, Faculty of Science, Cairo University, Cairo, Egypt.

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Mosselhi, M., Darwish, E. & Peseke, K. Synthesis and antimicrobial activity of imidazo- and pyrimido[2,1-f]-theophyllines. Monatsh Chem 139, 825–834 (2008). https://doi.org/10.1007/s00706-008-0854-z

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