Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2009 Nov;71(6):672-7.
doi: 10.4103/0250-474X.59551.

Synthesis and antimicrobial evaluation of 5-iodopyrimidine analogs

N M Goudgaon  1 , N J Basha, S B Patil
Affiliations

Synthesis and antimicrobial evaluation of 5-iodopyrimidine analogs

N M Goudgaon et al. Indian J Pharm Sci. 2009 Nov.

Abstract

4-Substituted-5-iodo-2-benzylthiopyrimidines were prepared efficiently in three steps. 2-Benzylthiopyrimidine on iodination in presence of base gave 5-iodo-2-benzylthiopyrimidine (1), which on chlorination with excess of POCl(3) furnished 4-chloro-5-iodo-2-benzylthiopyrimidine (2). Reaction of 2 with substituted aromatic amines, 2-aminopyridine and hydrazine hydrate yielded 4-amino-5-iodo-2-benzylthiopyrimidines 3(a-e), (3f) and (3g) respectively. Further, 4-hydrazino-5-iodo-2-benzylthiopyrimidine on condensation with substituted aromatic and heterocyclic aldehydes afforded the corresponding schiff bases 4(a-h). The structure of synthesized compounds have been established by spectral studies and elemental analysis. Synthesized compounds have been screened for antimicrobial activity. Compound 3f exhibited good antifungal activity against A. niger. The compounds 4a, 4c, 4d, 4g and 4h exhibited good antibacterial activity.

Keywords: 5-Substituted pyrimidine; Antibacterial; antifungal; schiff bases.

PubMed Disclaimer

Figures

Scheme 1
Scheme 1
Synthesis of 5-substituted pyrimidine analogs
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

References

    1. Jain KS, Chitre TS, Maniyar PB, Kathiravan MK, Bindre VS, Veer VS, et al. Biological and medicinal significance of pyrimidine. Current Sci. 2006;90:793–803.
    1. Mitsuya H, Weinhold KJ, Furman PA, St.Clair MH, Nusinoff-Lehman S, Gallo RC, et al. 3'-Azido-3'-deoxythymidine (BW A509U): An antiviral agent that inhibits the infectivity and cytopathic effect of human T-lymphotropic virus type III/lymphadenopathy-associated virus in vitro. Proc Natl Acad Sci USA. 1985;82:7096–100. - PMC - PubMed
    1. Lin TS, Guo JY, Schinazi RF, Chu CK, Xiang JN, Prusoff WH. Synthesis and antiviral activity of various 3-azido analogues of pyrimidine deoxyribonucleosides against human immunodeficiency virus (HIV-1, HTLV-III/LAV) J Med Chem. 1988;31:336–40. - PubMed
    1. Choo H, Chong Y, Choi Y, Mathew J, Schinazi RF, Chu CK. Synthesis, anti-HIV activity and molecular mechanism of drug resistance of L-2'.3'-didehydro-2',3'-dideoxy-2'-fluoro-4'-thionucleosides. J Med Chem. 2003;46:389–98. - PubMed
    1. Balzarini J, Pannecouque C, De Clercq E, Aquaro S, Perno CF, Egberink H, et al. Antiretrovirus activity of a novel class of acyclic pyrimidine nucleoside phosphonates. Antimicrob Agents Chemother. 2002;46:2185–93. - PMC - PubMed

LinkOut - more resources