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Molecules. 2015 Oct 22;20(10):19263-76. doi: 10.3390/molecules201019263.

Novel 2-Thioxanthine and Dipyrimidopyridine Derivatives: Synthesis and Antimicrobial Activity.

Author information

1
Organic Chemistry Department, Faculty of Pharmacy (Girls), ElAzhar University, Nasr City 11651, Egypt. s.elkalyoubi@hotmail.com.
2
Chemistry Department, Faculty of Science, Jazan University, Jazan (Female Section) 45142, Saudi Arabia. dr.fatmah2000@gmail.com.
3
Medical Chemistry Division, Faculty of Medicine, Jazan University, Jazan 82621, Saudi Arabia. syoussif@hotmail.com.
4
Chemistry Department, Faculty of Science, Zagazig University, Zagazig 44511, Egypt. syoussif@hotmail.com.

Abstract

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.

KEYWORDS:

6-amino-2-thiouracil; 6-amino-5-benzylideneamino-2-thiouracil; 8-aryl-3-methyl-2-methylthiopurine-6-ones; 8-aryl-3-methyl-2-thioxanthines

PMID:
26506337
PMCID:
PMC6332104
DOI:
10.3390/molecules201019263
[Indexed for MEDLINE]
Free PMC Article

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