16348-04-2

Usage

Uses

Used in Pharmaceutical Industry:
1-(4-METHYLPHENYL)PYRIMIDINE-2,4,6(1H,3H,5H)-TRIONE is used as a building block for the synthesis of new pharmaceuticals due to its unique structure and reactivity. Its potential in the development of novel drugs makes it a valuable asset in the pharmaceutical industry.
Used in Agrochemical Industry:
In the agrochemical industry, 1-(4-METHYLPHENYL)PYRIMIDINE-2,4,6(1H,3H,5H)-TRIONE is used as a key component in the development of new agrochemicals. Its unique properties contribute to the creation of innovative products for agricultural applications.
Used in Material Science:
1-(4-METHYLPHENYL)PYRIMIDINE-2,4,6(1H,3H,5H)-TRIONE is utilized as a component in the development of new materials. Its unique structure and reactivity allow for the creation of advanced materials with potential applications in various industries.
Used in Organic Chemistry Research:
As a promising building block, 1-(4-METHYLPHENYL)PYRIMIDINE-2,4,6(1H,3H,5H)-TRIONE is used in organic chemistry research for the synthesis of various organic compounds. Its unique properties make it an attractive candidate for further exploration and development in the field of organic chemistry.

InChI:InChI=1/C11H10N2O3/c1-7-2-4-8(5-3-7)13-10(15)6-9(14)12-11(13)16/h2-5H,6H2,1H3,(H,12,14,16)

Upstream product

• 622-51-5 p-tolylurea 
• 1663-67-8 malonoyl dichloride 
• 105-53-3 diethyl malonate 
• 141-82-2 malonic acid 
• 106-49-0 p-toluidine 
• 108-59-8 malonic acid dimethyl ester 

Downstream Products

• 1566577-44-3 (E)-5-((dimethylamino)methylene)-1-p-tolylpyrimidine-2,4,6-trione 
• 1566577-68-1 1-(4-methylphenyl)-5-((3-fluoro-4-(6-methoxy-7-(3-(pyrrolidin-1-yl)propoxy)quinolin-4-oxy)phenylamino)methylene)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1566577-76-1 1-(4-methylphenyl)-5-((3-fluoro-4-(6-methoxy-7-(3-(4-morpholinyl)propoxy)quinolin-4-oxy)phenylamino)methylene)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1566577-84-1 1-(4-methylphenyl)-5-((3-fluoro-4-(6-methoxy-7-(3-(4-methyl-1-piperazinyl)propoxy)quinolin-4-oxy)phenylamino)methylene)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1566577-52-3 1-(4-methylphenyl)-5-((3-fluoro-4-(6-methoxy-7-(3-(1-piperidinyl)propoxy)quinolin-4-oxy)phenylamino)methylene)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1566577-60-3 1-(4-methylphenyl)-5-((3-fluoro-4-(6-methoxy-7-(3-(4-methyl-1-piperidinyl)propoxy)quinolin-4-oxy)phenylamino)methylene)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 1923749-80-7 5-((1H-indol-2-yl)methylene)-1-(p-tolyl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 53855-71-3 1-(4-methylphenyl)-3-(4-methylphenylsulfonyl)pyrimidine-2,4,6-(1H,3H,5H)-trione 
• 1228963-47-0 1-(4-methylphenyl)-3-phenylsulfonylpyrimidine-2,4,6-(1H,3H,5H)-trione 
• 1228963-48-1 1-(4-methylphenyl)-3-(4-chlorophenylsulfonyl)pyrimidine-2,4,6-(1H,3H,5H)-trione 

Relevant academic research and scientific papers

Optimization of 5-arylidene barbiturates as potent, selective, reversible LSD1 inhibitors for the treatment of acute promyelocytic leukemia

Histone lysine specific demethylase 1 (LSD1) is overexpressed in diverse hematologic disorders and recognized as a promising target for blood medicines. In this study, molecular docking-based virtual screening united with bioevaluation was utilized to identify novel skeleton of 5-arylidene barbiturate as small-molecule inhibitors of LSD1. Among the synthesized derivatives, 12a exhibited reversible and potent inhibition (IC50 = 0.41 μM) and high selectivity over the MAO-A and MAO-B. Notably, 12a strongly induced differentiation effect on acute promyelocytic leukemia NB4 cell line and distinctly escalated the methylation level on histone 3 lysine 4 (H3K4). Our findings indicate that 5-arylidene barbiturate may represent a new skeleton of LSD1 inhibitors and 12a deserve as a promising agent for the further research.

Discovery of novel 6,7-disubstituted-4-phenoxyquinoline derivatives bearing 5-(aminomethylene)pyrimidine-2,4,6-trione moiety as c-Met kinase inhibitors

A series of novel quinoline derivatives bearing 5-(aminomethylene) pyrimidine-2,4,6-trione moiety were designed, synthesized, and evaluated for their c-Met kinase inhibitory activities and antiproliferative activities against 5 cancer cell lines (HT-29, H460, MKN-45, A549, and U87MG) in vitro. Most compounds showed moderate to excellent potency, with the most promising analogue 45 (c-Met half-maximal inhibitory concentration [IC50] = 1.15 nM) showing high selectivity versus 5 other tyrosine kinases, VEGFR-2, Flt-3, PDGFR-β, c-Kit, and EGFR. Structure-activity relationship studies indicated that electron-donating groups on the phenyl ring at the 3-position of pyrimidine-2,4,6-trione were required to increase the electron density on the 5-(aminomethylene)pyrimidine-2,4,6-trione moiety.

Synthesis and antitumor evaluation of novel cyclic arylsulfonylureas: ADME-T and pharmacophore prediction

Novel derivatives of 5-(substituted)benzylidene-3-(4-substituted)phenylsulfonylimidazolidine-2,4-diones (3a-r), 1-(4-substituted)phenylsulfonyl-3-(4-substituted)phenylpyrimidine-2,4,6-(1H,3H,5H)-triones (6a-l), and 3-(4-substituted)phenyl-1-(4-substituted)phenylsulfonylquinazoline-2,4(1H,3H)- diones (8a-l) have been synthesized and tested for their antitumor activity against 60 tumor cell lines taken from 9 different organs. The tested compounds have showed good inhibitory effect at the ovarian cancer (IGROV1) cell line. A significant inhibition for (RXF393) renal cancer cells was observed with series 3 compounds, while in the other two series 6 and 8, there was a significant inhibition of ovarian cancer cells (OVCAR-8) and melanoma cells (SK-MEL-2). Interestingly; beside the strong inhibition of compound 3q to IGROV1 and RXF393 cells, a great inhibition (199.62%) for (M14) Melanoma cells was observed at the tested concentration (10?μM). ADME-T and pharmacophore prediction methodology were used to study the antitumor activity of the most active compounds and to identify the structural features required for antitumor activity.

Synthesis of novel galactopyranosyl-derived spiro barbiturates

Malonic acid undergoes condensation readily with ureas to yield barbituric acids 2, which on bromination give 5,5-dibromobarbituric acids 3. Reaction of α-D-galactose with these 5,5-dibromo barbituric acids afforded 2,3-α-D-galactopyrano-1,4-dioxo-7,9-diaza-spiro[4,5]deca-6,8,10-triones 4. The structures of the products have been assigned on the basis of 1H NMR, 13C NMR, FAB-MS, optical activity, and elemental analysis. The title compounds are found to have antibacterial and antifungal activities.

Chemical modification of plant alkaloids. 2. Reaction of cotarnine with barbituric acid derivatives and structure of 5-dihydrocotarnylbarbituric acids

The reaction of barbituric acid and its N-substituted derivatives and 2-thio analogs with cotarnine forms 5-(4-methoxy-6-methyl-5,6,7,8-tetrahydro-2H-1,3-methylenedioxy-[4,5-g]isoquinolinyl-1)barbituric acids, a new class of zwitter-ions, the structure of which was studied by 1H and 13C NMR spectroscopy and mass spectrometry. The prepared compounds exist in solution as stable intermolecular associates and have a complicated H-bonded structure.