100186-95-6

Basic information

• Product Name: 1,3-dimethylthymine epoxide
• Synonyms: 1,3-dimethylthymine epoxide
• CAS NO: 100186-95-6
• Molecular Formula: C7H10N2O3
• Molecular Weight: 170.1659
• Mol File: 100186-95-6.mol

Chemical Properties

• Boiling Point: 246.1°Cat760mmHg
• Flash Point: 102.7°C
• Appearance: /
• Density: 1.349g/cm³
• Vapor Pressure: 0.0276mmHg at 25°C
• Refractive Index: 1.539
• CAS DataBase Reference: 1,3-dimethylthymine epoxide(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-dimethylthymine epoxide(100186-95-6)
• EPA Substance Registry System: 1,3-dimethylthymine epoxide(100186-95-6)

Safety Data

• Hazardous Substances Data: 100186-95-6(Hazardous Substances Data)

Usage

Chemical compound

A derivative of the nucleobase thymine, which is a key component of DNA and RNA.

Mutagenic properties

Tendency to cause changes in the genetic information of an organism, which can lead to mutations.

Carcinogenic properties

Potential to cause cancer by damaging the DNA in cells, leading to uncontrolled cell growth and tumor formation.

Medicinal chemistry and drug development

Studied for its potential applications in understanding the mechanisms of DNA damage and repair, which could contribute to the development of new therapeutic strategies.

Hazardous chemical

Due to its mutagenic and carcinogenic properties, 1,3-dimethylthymine epoxide is considered a hazardous chemical that requires careful handling in laboratory settings.

Ongoing research

Further studies are being conducted to better understand the biological effects and potential uses of this compound, which could lead to advancements in the fields of genetics, molecular biology, and drug development.

InChI:InChI=1/C7H10N2O3/c1-7-4(10)8(2)6(11)9(3)5(7)12-7/h5H,1-3H3

Upstream product

• 4401-71-2 1,3-dimethylthymine 
• 69596-94-7 dl-trans-5-bromo-6-hydroxy-1,3-dimethyl-5,6-dihydrothymine 
• 90001-70-0 5-bomo-6-hydroxy-1,3,5-trimethyldihydropyrimidine-2,4-(1H,3H)-dione 

Downstream Products

• 100187-02-8 (S)-2-((4R,5S)-5-Hydroxy-1,3,5-trimethyl-2,6-dioxo-hexahydro-pyrimidin-4-ylamino)-3-phenyl-propionic acid ethyl ester 
• 100187-02-8 (S)-2-((4S,5S)-5-Hydroxy-1,3,5-trimethyl-2,6-dioxo-hexahydro-pyrimidin-4-ylamino)-3-phenyl-propionic acid ethyl ester 
• 100187-02-8 (S)-2-((4R,5R)-5-Hydroxy-1,3,5-trimethyl-2,6-dioxo-hexahydro-pyrimidin-4-ylamino)-3-phenyl-propionic acid ethyl ester 
• 100187-02-8 (S)-2-((4S,5R)-5-Hydroxy-1,3,5-trimethyl-2,6-dioxo-hexahydro-pyrimidin-4-ylamino)-3-phenyl-propionic acid ethyl ester 
• 110918-92-8 (S)-2-((4R,5S)-5-Hydroxy-1,3,5-trimethyl-2,6-dioxo-hexahydro-pyrimidin-4-ylamino)-3-phenyl-propionic acid benzyl ester 
• 110918-92-8 (S)-2-((4S,5S)-5-Hydroxy-1,3,5-trimethyl-2,6-dioxo-hexahydro-pyrimidin-4-ylamino)-3-phenyl-propionic acid benzyl ester 

Relevant articles and documents

Selective oxidation of uracil and adenine derivatives by the catalytic system MeReO3/H2O2 and MeReO3/urea hydrogen peroxide

Methyltrioxorhenium (MTO) is a useful and selective catalyst for the oxidation of uracil and purine derivatives using environmentally friendly hydrogen peroxide (H2O2, 30% water solution) or hydrogen peroxide/urea adduct (UHP) as oxygen atom donors. In particular, the MTO/UHP system constitutes a convenient combination to convert uracil derivatives into the biologically relevant 5,6-oxiranyl-5,6-dihydrouracils in good yields. Purine derivatives are selectively oxidized to the corresponding 1-oxides, the best yield being obtained in the presence of pyrazine-2-carboxylic acid (PCA). The oxidation of the plasmid pBG1 is also reported as the first example of double-strand DNA cleavage mediated by the catalytic system MTO/H2O2. (C) 2000 Elsevier Science Ltd.

Dimethyldioxirane-Mn(Cl16)TDMPPCl porphyrin as efficient and chemoselective epoxidizing reagent of uracil derivatives

Dimethyldioxirane (DMDO) was employed as oxygen donor in metalloporphyrins catalyzed selective epoxidation of uracil derivatives.

The Reactivity of Thymine and Thymidine 5,6-Epoxides with Organometallic Reagents - A Route to Thymidine (6-4) Photoproduct Analogues

This report describes an efficient procedure for the generation and isolation of various thymine and thymidine 5,6-epoxides from the corresponding trans-5,6-bromohydrins by reaction with triethylamine. The quantitative isolation of the epoxides, accomplished by solvent precipitation of triethylamine hydrobromide, enabled their regiospecific ring-opening at C6 position by organometallic nucleophiles. The reaction was amenable to a broad range of alkyl, aryl, alkenyl, and alkynyl organomagnesium, -zinc, -aluminum, or -boron reagents, although the reactivity was strongly affected by the electronic effects of N3 protecting group. Additionally, the reaction featured excellent cis-diastereoselectivity providing access to C6-carbon-functionalized dihydrothymidine cis-alcohols, which are synthetic derivatives of UV-induced DNA lesions, namely, thymidine (6-4) photoproducts.

Studies on the chemistry of pyrimidine derivatives with dimethyldioxirane: Synthesis, cytotoxic effect and antiviral activity of new 5,6-oxiranyl-5,6-dihydro and 5-hydroxy-5,6-dihydro-6-substituted uracil derivatives and pyrimidine nucleosides

The oxidation of uracil derivatives and pyrimidine nucleosides performed in CH2Cl2 with dimethyldioxirane afforded new 5,6-oxiranyl-5,6-dihydro and cis-/trans-5,6-dihvdroxv-5,6-dihydro-derivatives. When the oxidations were performed in the presence of methanol as nucleophile cis- and trans- 5-hydroxy-6-methoxy-5,6-dihydro derivatives were obtained in acceptable yields. Cis- and trans-1,3- dimethyl-5-hydroxy-6-alkylamino-5,6-dihydro uracils were obtained by nucleophilic ring opening of the 1,3-dimethyl-5,6-oxiranyl-5,6-dihydro uracil in the purified form. Interestingly some of the new title products revealed low cytotoxicity and selective antiviral activity against DNA and RNA Viruses. In particular, compound 17b shows a strong and selective inhibition of the Sendai virus with lower effect on Herpes Simplex-1 virus. Compound 17b is also able to slightly inhibit HIV-1 virus at high concentrations, but in this case a cytotoxic effect was observed.

Oxidation of uracil derivatives and pyrimidine nucleosides by dimethyldioxirane: A new and mild synthesis of 5,6-oxiranyl-5,6-dihydro and 5,6-dihydroxy-5,6-dihydro-derivatives

The oxidation of title substrates with dimethyldioxirane afforded 5,6-oxiranyl-5,6-dihydro and cis- / trans-5,6-disubstituted-5,6-dihydro-derivatives.

Stereo Structures and Absolute Configurations of Reaction Products of dl-1,3-Dimethylthymine Epoxide with L-Amino Acid Ethyl Esters

Each reaction of dl-1,3-dimethylthymine epoxide (1) with L-amino acid ethyl esters (Pro-OEt, Met-OEt, Phe-OEt, and Trp-OEt) afforded the respective four optically active diastereomers 4-7, stereo structures of which were definitely elucidated as shown in