Publication:
Synthesis of N-substituted 5-iodouracils as antimicrobial and anticancer agents

0
0

Issued Date

2009

Resource Type

Article

File Type

application/pdf

ISSN

14203049

DOI

10.3390/molecules14082768

Other identifier(s)

2-s2.0-69549121667

Rights Holder(s)

Scopus

Bibliographic Citation

Molecules. Vol 14, No.8 (2009), p.2768-2779

Suggested Citation

Prachayasittikul S., Sornsongkhram N., Pingaew R., Worachartcheewan A., Ruchirawat S., Prachayasittikul V. Synthesis of N-substituted 5-iodouracils as antimicrobial and anticancer agents. Molecules. Vol 14, No.8 (2009), p.2768-2779. doi:10.3390/molecules14082768 Retrieved from: https://hdl.handle.net/20.500.14740/5704

Title

Synthesis of N-substituted 5-iodouracils as antimicrobial and anticancer agents

Author(s)

Prachayasittikul S.
 Sornsongkhram N.
 Pingaew R.
 Worachartcheewan A.
 Ruchirawat S.
 Prachayasittikul V.

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-C4H 9, s-C4H9, CH2C6H 11, 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.

Subject(s)

5-iodouracil
 Antiinfective agent
 Antimalarial agent
 Drug derivative
 Iodouracil
 Uracil
 Animal
 Article
 Chemical structure
 Chemistry
 Drug effect
 Human
 Microbiological examination
 Moraxella catarrhalis
 Neisseria mucosa
 Plasmodium falciparum
 Streptococcus pyogenes
 Synthesis
 Tumor cell line
 Animals
 Anti-Bacterial Agents
 Antimalarials
 Cell Line, Tumor
 Humans
 Microbial Sensitivity Tests
 Molecular Structure
 Moraxella (Branhamella) catarrhalis
 Neisseria mucosa
 Plasmodium falciparum
 Streptococcus pyogenes
 Uracil

View online Resources

Research Projects

Organizational Units

Journal Issue

URI

https://hdl.handle.net/20.500.14740/5704

Collections

Scopus: Year 1983-2021

Endorsement

Review

Supplemented By

Referenced By