Novel 2-Thioxanthine and Dipyrimidopyridine Derivatives: Synthesis and Antimicrobial Activity.
Several fused imidazolopyrimidines were synthesized starting from 6-amino-1-methyl-2-thiouracil (1) followed by nitrosation, reduction and condensation with different aromatic aldehydes to give Schiff's base. The dehydrocyclization of Schiff's bases using iodine/DMF gave Compounds 5a-g. The methylation of 5a-g using a simple alkylating agent as dimethyl sulfate ((CH₃)₂SO₄) gave either monoalkylated imidazolopyrimidine 6a-g at room temperature or dialkylated derivatives 7a-g on heating 6a-g with ((CH₃)₂SO₄). On the other hand, treatment of 1 with different aromatic aldehydes in absolute ethanol in the presence of conc. hydrochloric acid at room temperature and/or reflux with acetic acid afforded bis-5,5́-diuracylmethylene 8a-e, which cyclized on heating with a mixture of acetic acid/HCl (1:1) to give 9a-e. Compounds 9a-e can be obtained directly by refluxing of Compound 1 with a mixture of acetic acid/HCl. The synthesized new compounds were screened for antimicrobial activity, and the MIC was measured.
Organic Chemistry Department, Faculty of Pharmacy (Girls), ElAzhar University, Nasr City 11651, Egypt. s.elkalyoubi@hotmail.com.
Samar
S
El-kalyoubi
Chemistry Department, Faculty of Science, Jazan University, Jazan (Female Section) 45142, Saudi Arabia. dr.fatmah2000@gmail.com.
Fatmah
F
Agili
Medical Chemistry Division, Faculty of Medicine, Jazan University, Jazan 82621, Saudi Arabia. syoussif@hotmail.com.|Chemistry Department, Faculty of Science, Zagazig University, Zagazig 44511, Egypt. syoussif@hotmail.com.
Shaker
S
Youssif
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002176:Candida albicans / Q000187:drug effects; D003500:Cyclization; D004926:Escherichia coli / Q000187:drug effects; D008745:Methylation; D008826:Microbial Sensitivity Tests; D010084:Oxidation-Reduction; D011725:Pyridines / Q000138:chemical synthesis* / Q000494:pharmacology; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects; D013892:Thioxanthenes / Q000138:chemical synthesis* / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D011725:Pyridines; D011743:Pyrimidines; D013892:Thioxanthenes
6-amino-2-thiouracil; 6-amino-5-benzylideneamino-2-thiouracil; 8-aryl-3-methyl-2-methylthiopurine-6-ones; 8-aryl-3-methyl-2-thioxanthines