16350-59-7

Basic information

• Product Name: 5-(methylsulfanyl)pyrimidine-2,4(1H,3H)-dione
• CAS NO: 16350-59-7
• Molecular Formula: C₅H₆N₂O₂S
• Molecular Weight: 158.1783
• Mol File: 16350-59-7.mol
• Article Data: 8

Chemical Properties

• Density: 1.43g/cm³
• Refractive Index: 1.614
• CAS DataBase Reference: 5-(methylsulfanyl)pyrimidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-(methylsulfanyl)pyrimidine-2,4(1H,3H)-dione(16350-59-7)
• EPA Substance Registry System: 5-(methylsulfanyl)pyrimidine-2,4(1H,3H)-dione(16350-59-7)

Safety Data

• Hazardous Substances Data: 16350-59-7(Hazardous Substances Data)

Usage

General Description

5-(methylsulfanyl)pyrimidine-2,4(1H,3H)-dione, also known as 5-(methylthio)cytosine, is a chemical compound with the molecular formula C5H6N2O2S. It is a derivative of cytosine, a nucleobase commonly found in DNA and RNA. 5-(methylsulfanyl)pyrimidine-2,4(1H,3H)-dione contains a pyrimidine ring with a methylsulfanyl group attached to the 5-carbon position, and a ketone group located at the 2 and 4 positions. 5-(methylsulfanyl)pyrimidine-2,4(1H,3H)-dione has potential applications in pharmaceuticals and organic synthesis, and its structure may be of interest in medicinal chemistry research. It also has the potential to be used as a mutagen to induce mutations in various organisms for genetic studies.

Upstream product

• 2949-92-0 methanethiosulfonic acid S-methyl ester 
• 696-07-1 5-iodouracil 
• 51-20-7 5-bromouracil 
• 5188-07-8 sodium thiomethoxide 
• 14020-53-2 5-mercapto uracil 
• 74-88-4 methyl iodide 

Downstream Products

• 514842-56-9 2,4-dichloro-5-(methylsulfonyl)pyrimidine 
• 7401-98-1 2,4-dichloro-5-methylsulfanylpyrimidine 
• 1313720-30-7 4-(5-(methylthio)-4-morpholinopyrimidin-2-yl)benzenamine 
• 1313720-33-0 1-(4-(5-(methylthio)-4-morpholinopyrimidin-2-yl)phenyl)-3-phenylurea 
• 1313720-37-4 phenyl 4-(5-(methylthio)-4-morpholinopyrimidin-2-yl)phenylcarbamate 
• 1313720-52-3 1-(2-aminophenyl)-3-(4-(5-(methylthio)-4-morpholinopyrimidin-2-yl)phenyl)thiourea 
• 1313720-54-5 N-(4-(5-(methylthio)-4-morpholinopyrimidin-2-yl)phenyl)-1H-benzo[d]imidazol-2-amine 
• 1313720-69-2 phenyl 4-(5-(methylsulfinyl)-4-morpholinopyrimidin-2-yl)phenylcarbamate 

Relevant articles and documents

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As tyrosine kinase inhibitors of the nitrogen-containing heteroaromatic ring derivatives

The present invention relates to compounds as represented by general formula (I) as tyrosine kinase inhibitors, preparation method thereof, pharmaceutical compositions containing the compounds, and uses thereof for preventing and/or treating instances of B-cell related leukemia, inflammatory diseases and autoimmune diseases, wherein A, ring B, L1, L2, R1, R2, R3, a, b, c, d, e, p and q are as defined in the specification.

Synthesis and structure-activity relationship studies of N -benzyl-2-phenylpyrimidin-4-amine derivatives as potent usp1/uaf1 deubiquitinase inhibitors with anticancer activity against nonsmall cell lung cancer

Deregulation of ubiquitin conjugation or deconjugation has been implicated in the pathogenesis of many human diseases including cancer. The deubiquitinating enzyme USP1 (ubiquitin-specific protease 1), in association with UAF1 (USP1-associated factor 1), is a known regulator of DNA damage response and has been shown as a promising anticancer target. To further evaluate USP1/UAF1 as a therapeutic target, we conducted a quantitative high throughput screen of >400000 compounds and subsequent medicinal chemistry optimization of small molecules that inhibit the deubiquitinating activity of USP1/UAF1. Ultimately, these efforts led to the identification of ML323 (70) and related N-benzyl-2-phenylpyrimidin-4-amine derivatives, which possess nanomolar USP1/UAF1 inhibitory potency. Moreover, we demonstrate a strong correlation between compound IC50 values for USP1/UAF1 inhibition and activity in nonsmall cell lung cancer cells, specifically increased monoubiquitinated PCNA (Ub-PCNA) levels and decreased cell survival. Our results establish the druggability of the USP1/UAF1 deubiquitinase complex and its potential as a molecular target for anticancer therapies.

Functionalization of unprotected uracil derivatives using the halogen - Magnesium exchange

The reaction of commercially available 5-iodouracil with 2 equiv of MeMgCl in the presence of LiCl, followed by the addition of i-PrMgCl-LiCl, provides the corresponding trimagnesiated species, which reacts with various electrophiles to give selectively 5