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Molecules 2015, 20(10), 19263-19276; doi:10.3390/molecules201019263

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

1
Organic Chemistry Department, Faculty of Pharmacy (Girls), ElAzhar University, Nasr City 11651, Egypt
2
Chemistry Department, Faculty of Science, Jazan University, Jazan (Female Section) 45142, Saudi Arabia
3
Medical Chemistry Division, Faculty of Medicine, Jazan University, Jazan 82621, Saudi Arabia
4
Chemistry Department, Faculty of Science, Zagazig University, Zagazig 44511, Egypt
Oral Presentation at the 1st International Turkic World Conference on Chemical Sciences and Technologies October 2015.
*
Author to whom correspondence should be addressed.
Academic Editor: Philippe Belmont
Received: 22 August 2015 / Revised: 3 October 2015 / Accepted: 12 October 2015 / Published: 22 October 2015
(This article belongs to the Collection Heterocyclic Compounds)
View Full-Text   |   Download PDF [728 KB, uploaded 22 October 2015]   |  

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 5ag. The methylation of 5ag using a simple alkylating agent as dimethyl sulfate ((CH3)2SO4) gave either monoalkylated imidazolopyrimidine 6ag at room temperature or dialkylated derivatives 7ag on heating 6ag 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 8ae, which cyclized on heating with a mixture of acetic acid/HCl (1:1) to give 9ae. Compounds 9ae 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. View Full-Text
Keywords: 6-amino-2-thiouracil; 6-amino-5-benzylideneamino-2-thiouracil; 8-aryl-3-methyl-2-thioxanthines; 8-aryl-3-methyl-2-methylthiopurine-6-ones 6-amino-2-thiouracil; 6-amino-5-benzylideneamino-2-thiouracil; 8-aryl-3-methyl-2-thioxanthines; 8-aryl-3-methyl-2-methylthiopurine-6-ones
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

El-kalyoubi, S.; Agili, F.; Youssif, S. Novel 2-Thioxanthine and Dipyrimidopyridine Derivatives: Synthesis and Antimicrobial Activity. Molecules 2015, 20, 19263-19276.

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