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Synthesis of N-Substituted 5-Iodouracils as Antimicrobial and Anticancer Agents
Department of Chemistry, Faculty of Science, Srinakharinwirot University, Bangkok 10110, Thailand
Department of Clinical Microbiology, Faculty of Medical Technology, Mahidol University, Bangkok 10700, Thailand
Laboratory of Medicinal Chemistry, Chulabhorn Research Institute, Bangkok 10210, Thailand
* Authors to whom correspondence should be addressed.
Received: 6 July 2009; in revised form: 15 July 2009 / Accepted: 27 July 2009 / Published: 27 July 2009
Abstract: This study reports the synthesis of some substituted 5-iodouracils and their bioactivities. Alkylation of 5-iodouracils gave predominately N1-substituted-(R)-5-iodouracil compounds 7a-d (R = n-C4H9, s-C4H9, CH2C6H11, CH2C6H5) together with N1,N3-disubstituted (R) analogs 8a-b (R = n-C4H9, CH2C6H11). Their antimicrobial activity was tested against 27 strains of microorganisms using the agar dilution method. The analogs 7a, 7c and 7d displayed 25-50% inhibition against Branhamella catarrhalis, Neisseria mucosa and Streptococcus pyogenes at 0.128 mg/mL. No antimalarial activity was detected for any of the analogs when tested against Plasmodium falciparum (T9.94). Their anticancer activity was also examined. Cyclohexylmethyl analogs 7c and 8b inhibited the growth of HepG2 cells. Significantly, N1,N3-dicyclohexylmethyl analog 8b displayed the most potent anticancer activity, with an IC50 of 16.5 mg/mL. These 5-iodouracil analogs represent a new group of anticancer and antibacterial agents with potential for development for medicinal applications.
Keywords: 5-iodouracil analogs; N-alkylation; antibacterial; antimalarial; anticancer activities
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Prachayasittikul, S.; Sornsongkhram, N.; Pingaew, R.; Worachartcheewan, A.; Ruchirawat, S.; Prachayasittikul, V. Synthesis of N-Substituted 5-Iodouracils as Antimicrobial and Anticancer Agents. Molecules 2009, 14, 2768-2779.
Prachayasittikul S, Sornsongkhram N, Pingaew R, Worachartcheewan A, Ruchirawat S, Prachayasittikul V. Synthesis of N-Substituted 5-Iodouracils as Antimicrobial and Anticancer Agents. Molecules. 2009; 14(8):2768-2779.
Prachayasittikul, Supaluk; Sornsongkhram, Nirun; Pingaew, Ratchanok; Worachartcheewan, Apilak; Ruchirawat, Somsak; Prachayasittikul, Virapong. 2009. "Synthesis of N-Substituted 5-Iodouracils as Antimicrobial and Anticancer Agents." Molecules 14, no. 8: 2768-2779.