130278-40-9

Usage

Derivative of pyrimidine

The compound is based on a pyrimidine ring, which is a heterocyclic compound commonly found in nucleic acids.

Used as an intermediate

2-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)acetonitrile is used as an intermediate in the synthesis of pharmaceuticals and agrochemicals.

Unique structure

The structure of the compound consists of a pyrimidine ring with two ketone groups and an acetonitrile group attached to it, making it a versatile building block for the synthesis of various compounds.

Potential applications in medicinal chemistry and drug discovery

Due to its unique structure and properties, the compound may have potential applications in medicinal chemistry and drug discovery.

Upstream product

• 107-14-2 chloroacetonitrile 
• 10457-14-4 O,O'-bis-(trimethylsilyl)uracil 
• 590-17-0 cyanomethyl bromide 
• 66-22-8 uracil 
• 872358-29-7 1-cyanomethyl-2-ethoxypyrimidin-4-one 

Downstream Products

• 161686-67-5 3-benzyl-1-(cyanomethyl)uracil 
• 161686-68-6 3-(p-methoxybenzyl)-1-(cyanomethyl)uracil 

Relevant academic research and scientific papers

One-pot click synthesis of 1,2,3-triazole-embedded unsaturated uracil derivatives and hybrids of 1,5- and 2,5-disubstituted tetrazoles and pyrimidines

Novel conformationally restricted pyrimidine derivatives with a 1,2,3-triazolyl scaffold bound via Z- and E-2-butenyl spacers were prepared by Cu(I)-catalyzed click chemistry via a one-pot, multi-step reaction under microwave irradiation, while 1,5- and 2,5-disubstituted tetrazoles were synthesized by convenient, environmentally friendly click synthesis and subsequently by N-alkylation of 5-substituted 1H-tetrazoles. Among all the tested compounds, the N-1,N-3-disubstituted olefinic uracil derivative showed the highest antiproliferative effects.

HMDS/KI a simple, a cheap and efficient catalyst for the one-pot synthesis of N-functionalized pyrimidines

The syntheses of N-Alkylpyrimidine derivatives by reacting pyrimidin-2,4-diones with appropriate alkyl halide under microwave irradiation at 400 W were compared to the conventional synthesis route. These methodologies are regioselective and compatible with numerous substrates and furnish the corresponding N-alkylpyrimidines in good yields using a cheap catalyst HMDS/KI in MeCN. A comparison study between these two different modes of heating was investigated.

Synthesis, antifungal evaluation and molecular docking studies of some tetrazole derivatives

A facile and simple protocol for the [3+2] cycloaddition of alkyl nitriles (RCN) with sodium azide (NaN3) in the presence of copper bis(diacetylcurcumin) 1,2-diamin-obenzene Schiff base complex, SiO2-[Cu-BDACDABSBC] as a heterogeneous catalyst in the presence of ascorbic acid and a solution of water/i-PrOH (50:50, V/V) media at reflux condition is described. The supported catalyst was prepared by immobilization of a copper bis(diacetylcurcumin) 1,2-diaminobenzene Schiff base complex [Cu-BDACDABSBC] on silica gel. The complex has high selectivity, catalytic activity, and recyclability. The significant features of this procedure are high yields, broad substrate scope and simple and efficient work-up procedure. According to this synthetic methodology, excellent yields of 5-substituted 1H-tetrazoles having bioactive N-heterocyclic cores were synthesized. The in vitro antifungal activities of title compounds were screened against various pathogenic fungal strains, such as Candida species involving C. albicans, C. glabrata, C. krusei, C. parapsilosis as well as filamentous fungi like Aspergillus species consisting of A. fumigatus and A. flavus. The molecular docking analysis is discussed for one most potent compound against fungi. The docking study determined a remarkable interaction between the most potent compounds and the active site of Mycobacterium P450DM.

An efficient protocol for facile synthesis of new 5-substituted-1H-tetrazole derivatives using copper-doped silica cuprous sulfate (CDSCS) as heterogeneous nano-catalyst

A facile and highly efficient protocol for synthesis of new 5-substituted-1H-tetrazoles derivatives using copper-doped silica cuprous sulfate (CDSCS) is described. In this method, the cycloaddition reaction of sodium azide with structurally diverse nitriles involving bioactive N-heterocyclic cores exploiting CDSCS in refluxing H2O/i-PrOH (1:1, v/v) furnishes the corresponding 5-substituted-1H-tetrazoles in good to excellent yields (up to 93percent). The influence of parameters effective in progress of reaction including solvent type, temperature and catalyst was studied and discussed. In this protocol, CDSCS was proved to be an efficient heterogeneous nano-catalyst to easily achieve the new tetrazole derivatives. The advantages of CDSCS in current protocol known are its cheapness, thermal and chemical stability, ease of recyclability and reusability for several consecutive runs without significant decline in its reactivity.

Cu/Graphene/Clay Nanohybrid: A Highly Efficient Heterogeneous Nanocatalyst for Synthesis of New 5-Substituted-1H-Tetrazole Derivatives Tethered to Bioactive N-Heterocyclic Cores

A series of new 5-substituted 1H-tetrazoles bearing bioactive N-heterocyclic cores were synthesized through [3 + 2] cycloaddition reactions between alkyl nitriles (RCN) and NaN3in the presence of Cu/aminoclay/reduced graphene oxide nanohybrid (Cu/AC/r-GO nanohybrid) as a heterogeneous nanocatalyst in water/i-PrOH (50:50, V/V) media at reflux condition. The influence of factors on a sample reaction including solvent type, temperature, and catalyst amount was discussed. This current protocol has many advantages including inexpensiveness, environmentally benign, broad substrate scope, excellent yields, and easy work-up procedure. The Cu/AC/r-GO used in this protocol is a low-cost catalyst that proved to have considerable chemical and thermal stabilities. This non-hygroscopic catalyst can be easily recycled, reused, and stored for many consecutive reaction runs without significant loss in its reactivity.

Silica sulfuric acid (SSA) as a highly efficient heterogeneous catalyst for persilylation of purine and pyrimidine nucleobases and other N-heterocycles using HMDS

Purine and pyrimidine nucleobases and other N-heterocycles have been silylated with HMDS in excellent yields in the presence of a catalytic amount of silica sulfuric acid (SSA) as a heterogeneous catalyst. SSA utilizes a shorter reaction time and higher yields of silylated nucleobases. SSA is reusable for several times without a decrease in reactivity or yield of silylated adducts. Copyright

Synthesis and pharmacology of willardiine derivatives acting as antagonists of kainate receptors

The natural product willardiine (8) is an AMPA receptor agonist while 5-iodowillardiine (10) is a selective kainate receptor agonist. In an attempt to produce antagonists of kainate and AMPA receptors analogues of willardiine with substituents at the N3 position of the uracil ring were synthesized. The N3-4-carboxybenzyl substituted analogue (38c) was found to be equipotent at AMPA and GLUK5-containing kainate receptors in the neonatal rat spinal cord. The N3-2-carboxybenzyl substituted analogue (38a) proved to be a potent and selective GLUK5 subunit containing kainate receptor antagonist when tested on native rat and human recombinant AMPA and kainate receptor subtypes. The GLUK5 kainate receptor antagonist activity was found to reside in the S enantiomer (44a) whereas the R enantiomer (44b) was almost inactive. 5-Iodo substitution of the uracil ring of 44a gave 45, which was found to have enhanced potency and selectivity for GLU K5.