42747-84-2

Basic information

• Product Name: 3-Methyl-6-(1-Methylhydrazin-1-yl)-1,2,3,4- tetrahydropyriMidine-2,4-dione
• Synonyms: 3-Methyl-6-(1-Methylhydrazin-1-yl)-1,2,3,4- tetrahydropyriMidine-2,4-dione;3-Methyl-6-(1-Methylhydrazinyl)pyriMidine-2,4(1H,3H)-dione;3-Methyl-6-(N-methyl-hydrazino)-1H-pyrimidine-2,4-dione
• CAS NO: 42747-84-2
• Molecular Formula: C₆H₁₀N₄O₂
• Molecular Weight: 170.1692
• Mol File: 42747-84-2.mol
• Article Data: 8

Chemical Properties

• Appearance: /
• Density: 1.39±0.1 g/cm3(Predicted)
• PKA: 9.66±0.40(Predicted)
• CAS DataBase Reference: 3-Methyl-6-(1-Methylhydrazin-1-yl)-1,2,3,4- tetrahydropyriMidine-2,4-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Methyl-6-(1-Methylhydrazin-1-yl)-1,2,3,4- tetrahydropyriMidine-2,4-dione(42747-84-2)
• EPA Substance Registry System: 3-Methyl-6-(1-Methylhydrazin-1-yl)-1,2,3,4- tetrahydropyriMidine-2,4-dione(42747-84-2)

Safety Data

• Hazardous Substances Data: 42747-84-2(Hazardous Substances Data)

Upstream product

• 4318-56-3 3-methyl-6-chlorouracil 
• 60-34-4 methylhydrazine 

Downstream Products

• 647023-79-8 C₁₈H₁₈N₄O₄ 
• 91284-70-7 1,6-dimethyl-3,4-diphenyl-4,8-dihydro-4-deazatoxoflavin 
• 91284-71-8 1,3,6-trimethyl-4-phenyl-4,8-dihydro-4-deazatoxoflavin 

Relevant articles and documents

Rational design, synthesis and biological profiling of new KDM4C inhibitors

The human histone demethylases of the KDM4 family have been related to diseases such as prostate and breast cancer. Majority of currently known inhibitors suffer from the low permeability and low selectivity between the enzyme isoforms. In this study, toxoflavin motif was used to design and synthesize new KDM4C inhibitors with improved biological activity and in vitro ADME properties. Inhibitors displayed good passive cellular permeability and metabolic stability. However, diminishing of redox liability and consequently non-specific influence on cell viability still remains a challenge.

Convenient synthesis of toxoflavin that targets β-catenin/TCF4 signaling activities

A rapid and improved route for synthesis of toxoflavin, an antibiotic and antitumor agent, is described. The method uses easily obtained materials and simple and practical reactions, including chlorination, condensation, and diazotization to produce toxoflavin in five steps with 14.2% yield and 98.6% purity (HPLC). This synthetic toxoflavin effectively inhibited β-catenin/Tcf4 driven TOP-luciferase activity with an IC50 of less than 0.5 μM and induced colon cancer cell death in a dose-dependent manner with an IC50 of 0.29 μM.

Toxoflavins and deazaflavins as the first reported selective small molecule inhibitors of tyrosyl-DNA phosphodiesterase II

The recently discovered enzyme tyrosyl-DNA phosphodiesterase 2 (TDP2) has been implicated in the topoisomerase-mediated repair of DNA damage. In the clinical setting, it has been hypothesized that TDP2 may mediate drug resistance to topoisomerase II (topo II) inhibition by etoposide. Therefore, selective pharmacological inhibition of TDP2 is proposed as a novel approach to overcome intrinsic or acquired resistance to topo II-targeted drug therapy. Following a high-throughput screening (HTS) campaign, toxoflavins and deazaflavins were identified as the first reported sub-micromolar and selective inhibitors of this enzyme. Toxoflavin derivatives appeared to exhibit a clear structure-activity relationship (SAR) for TDP2 enzymatic inhibition. However, we observed a key redox liability of this series, and this, alongside early in vitro drug metabolism and pharmacokinetics (DMPK) issues, precluded further exploration. The deazaflavins were developed from a singleton HTS hit. This series showed distinct SAR and did not display redox activity; however low cell permeability proved to be a challenge.