Molecules 2009, 14(8), 2768-2779; doi:10.3390/molecules14082768
Article

Synthesis of N-Substituted 5-Iodouracils as Antimicrobial and Anticancer Agents

Supaluk Prachayasittikul 1,* email, Nirun Sornsongkhram 1 , Ratchanok Pingaew 1 , Apilak Worachartcheewan 2 , Somsak Ruchirawat 3  and Virapong Prachayasittikul 2,* email
1 Department of Chemistry, Faculty of Science, Srinakharinwirot University, Bangkok 10110, Thailand 2 Department of Clinical Microbiology, Faculty of Medical Technology, Mahidol University, Bangkok 10700, Thailand 3 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
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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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Cite This Article

MDPI and ACS Style

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.

AMA Style

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.

Chicago/Turabian Style

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.

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