Publication: Synthesis of N-Substituted 5-Iodouracils as antimicrobial and anticancer agents
Issued Date
2009
Resource Type
Language
eng
ISSN
1420-3049
Bibliographic Citation
Molecules. Vol.14, No.8 (2009), 2768-2779
Suggested Citation
Supaluk Prachayasittikul, Nirun Sornsongkhram, Ratchanok Pingaew, Apilak Worachartcheewan, Somsak Ruchirawat, Virapong Prachayasittikul Synthesis of N-Substituted 5-Iodouracils as antimicrobial and anticancer agents. Molecules. Vol.14, No.8 (2009), 2768-2779. Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/2113
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Title
Synthesis of N-Substituted 5-Iodouracils as antimicrobial and anticancer agents
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 g/mL. These 5-
iodouracil analogs represent a new group of anticancer and antibacterial agents with
potential for development for medicinal applications.