134218-80-7

Upstream product

• 696-07-1 5-iodouracil 
• 536-74-3 phenylacetylene 
• 51-20-7 5-bromouracil 

Downstream Products

• 1396408-78-8 1-(methoxymethyl)-5-(phenylethynyl)pyrimidin-2,4-dione 
• 1396409-34-9 1,3-bis(methoxymethyl)-5-(phenylethynyl)pyrimidin-2,4-dione 
• 21325-46-2 5-phenethyl-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

The synthesis and antituberculosis activity of 5-alkynyl uracil derivatives

A series of new 5-alkynyl-substituted uracil and uridine derivatives were synthesised via palladium-catalysed Sonogashira cross-coupling reaction of 5-bromo-pyrimidine base with terminal acetylenes with good yields in DMF at room temperature. All obtained compounds were tested for antimycobacterial activity against Mycobacetrium bovis and Mycobacterium tuberculosis (H37Ra) at concentrations of 1–100 μg/ml using MABA test. Obtained results revealed that most of tested uracil derivatives exhibited high antimycobacterial activity (MIC50 = 1.1–19.2 μg/ml) in comparison with therapeutic agents such as rifampicin, isoniazid and D-cycloserine, excluding compounds having alkyl substituent at triple alkyne bond.

A facile synthesis of fluorophores based on 5-phenylethynyluracils

Compact, fluorescent uracil aglycones and derivatives suitable for incorporation into the oligonucleotide mimic peptide nucleic acid (PNA) have been prepared by Sonogashira/Castro-Stephens coupling to monosubstituted phenylacetylenes. Cyclic 6-(phenyl)furo[2,3-d]pyrimidin-2(3H)-ones were accessed by the Ag+-catalyzed cyclization of the 5-alkynyluracil precursors. Although this reaction was sluggish, it gave quantitative chemical yields. Electron-rich alkynes, such as p-methoxyphenylethyne, cyclize much more rapidly than electron-deficient alkynes. Adjustment of the reaction conditions permitted the synthesis of p-nitrophenylfuranouracil in excellent yield. Georg Thieme Verlag Stuttgart.

Efficient palladium-mediated or base-induced 5-endo-dig cyclisation of C5-alkynylated pyrimidine derivatives: Conventional and microwave-assisted synthesis of novel furo[2,3-d]pyrimidines

A series of the novel 5-alkynyl- and furo[2,3-d]pyrimidine derivatives in which the sugar moiety is replaced by a methoxymethyl (MOM) group is synthesised using the Sonogashira cross-coupling reaction under both conventional and microwave conditions, in g

Inhibition of mycobacterial replication by pyrimidines possessing various C-5 functionalities and related 2′-deoxynucleoside analogues using in vitro and in vivo models

Tuberculosis (TB) has become an increasing problem since the emergence of human immunodeficiency virus and increasing appearance of drug-resistant strains. There is an urgent need to advance our knowledge and discover a new class of agents that are distin

Efficient solvent- and metal-free Sonogashira protocol catalysed by 1,4-diazabicyclo(2.2.2) octane (DABCO)

An efficient metal-free Sonogashira coupling protocol catalysed by DABCO is reported, where very good conversions and selectivities to the cross-coupling product were obtained under mild reaction conditions. The reported solvent-, phosphane- and metal-free protocol, that uses a cheap base as catalyst, considerably improves the green credentials of the reaction.

DNA-protein cross-linking: Model systems for pyrimidine-aromatic amino acid cross-linking

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.