13345-11-4Relevant academic research and scientific papers
Desulfurization of 2-thioxo-1,2,3,4-tetrahydropyrimidin-4-ones with oxiranes and 2-haloacetonitriles
Novakov,Orlinson,Navrotskii
, p. 607 - 609 (2005)
A procedure was developed for the synthesis of tetrahydropyrimidine-2,4- diones by desulfurization of 2-thioxo-1,2,3,4-tetrahydropyrimidin-4-ones with oxiranes or 2-haloacetonitriles in polar solvents in the presence of a base.
Solid-phase synthesis (SPS) of substituted uracils via Oxone cleavage methodology
Petricci, Elena,Renzulli, Michela,Radi, Marco,Corelli, Federico,Botta, Maurizio
, p. 9667 - 9670 (2002)
An original and highly efficient Oxone cleavage methodology for the solid-phase synthesis of substituted uracils has been developed. An example of application of this methodology to the solid-phase synthesis of uridine derivatives is also reported.
Design, synthesis, and biological evaluation of 1-[(2-benzyloxyl/alkoxyl) methyl]-5-halo-6-aryluracils as potent HIV-1 non-nucleoside reverse transcriptase inhibitors with an improved drug resistance profile
Wang, Xiaowei,Zhang, Jianfang,Huang, Yang,Wang, Ruiping,Zhang, Liang,Qiao, Kang,Li, Li,Liu, Chang,Ouyang, Yabo,Xu, Weisi,Zhang, Zhili,Zhang, Liangren,Shao, Yiming,Jiang, Shibo,Ma, Liying,Liu, Junyi
, p. 2242 - 2250 (2012/05/20)
Because the emergence of drug-resistant mutants has limited the efficacy of non-nucleoside reverse transcriptase inhibitors (NNRTIs), it is essential to develop new antivirals with better drug resistance and pharmacokinetic profiles. Here we designed and synthesized a series of 1-[(2-benzyloxyl/alkoxyl)methyl]- 5-halo-6-aryluracils, the HEPT analogues, and evaluated their biological activity using nevirapine and 18 (TNK-651) as reference compounds. Most of these compounds, especially 6b, 7b, 9b, 11b, and 7c, exhibited highly potent anti-HIV-1 activity against both wild-type and NNRTI-resistant HIV-1 strains. Compound 7b, which had the highest selectivity index (SI = 38 215), is more potent than nevirapine and 18. These results suggest that the introduction of a halogen at the C-5 position may contribute to the effectiveness of these compounds against RTI-resistant variants. In addition, meta substituents on the C-6 aromatic moiety could significantly enhance activity against NNRTI-resistant HIV-1 strains. These compounds can be further developed as next-generation NNRTIs with an improved antiviral efficacy and drug-resistance profile.
Novel synthetic route for 5-substituted 6-arylmethylluracils from 2,4,6-trichloropyrimidines
Loksha, Yasser M.
experimental part, p. 1296 - 1301 (2010/03/23)
(Chemical Equation Presented) Treatment of 2,4,6-trichloropyrimidines (1a,b) with the sodium salt of benzyl cyanide derivatives (2a,b) afforded 5-substituted 4-aryl(cyanomethyl)-2,6-dichloropyrimidines (3a-f). Compounds 3a,b were alkylated with methyl iod
DNA-protein cross-linking: Model systems for pyrimidine-aromatic amino acid cross-linking
Sun, Guangxing,Fecko, Christopher J.,Nicewonger, Robert B.,Webb, Watt W.,Begley, Tadhg P.
, p. 681 - 683 (2007/10/03)
We have synthesized simple model systems to explore the possibility of photo-cross-linking between the pyrimidine bases and the side chains of the aromatic amino acids. Thymine/phenylalanine and thymine/tyrosine models gave cross-links, and thymine/tryptophan models gave complex mixtures; the cytosine/phenylalanine model was unreactive. The quantum yields for the model cross-linking reactions were 18-46 times smaller than those for thymine dimer formation. Biphotonic excitation contributes little to the yield of these reactions.
