110524-36-2

Usage

Chemical class

Pyrimidine analog

Structure

1-(3-deoxy-3-methyl-beta-D-arabinofuranosyl)pyrimidine-2,4(1H,3H)-dione

Analog of

Deoxycytidine

Activity

Potential antineoplastic (anticancer)

Mechanism of action

Inhibition of DNA synthesis through incorporation into DNA and inhibition of ribonucleotide reductase enzyme

Potential applications

Chemotherapy for various forms of cancer, including leukemia and solid tumors

Current status

Further research and clinical trials needed to understand therapeutic uses

Upstream product

• 959843-61-9 1-(2-O-acetyl-5-O-benzoyl-3-deoxy-3-C-methyl-β-D-ribofuranosyl)uracil 
• 1065271-30-8 1-(5-O-benzoyl-3-deoxy-3-C-methyl-β-D-ribofuranosyl)uracil 
• 58-96-8 uridine 
• 81246-79-9 5'-dimethoxytrityluridine 
• 114551-06-3 2’,3’-di-O-(methanesulfonyl)-5’-O-(4,4’-dimethoxytrityl)-uridine 
• 114551-07-4 2’,3’-anhydro-5’-O-(4,4’-dimethoxytrityl)-1-β-D-lyxofuranosyl-uracil 
• 75-24-1 trimethylaluminum 
• 14999-47-4 1-(2,3-anhydro-5-O-benzoyl-β-D-lyxofuranosyl)uracil 
• 14042-38-7 1-(2,3-anhydro-β-D-lyxofuranosyl)uracil 
• 77-76-9 2,2-dimethoxy-propane 
• 96253-10-0 1-[2,3-epoxy-5-O-(triphenylmethyl)-β-D-lyxofuranosyl]pyrimidine-2,4(1H,3H)-dione 
• 114551-17-6 1-{(2R,3S,4S,5S)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-3-hydroxy-4-methyl-tetrahydro-furan-2-yl}-1H-pyrimidine-2,4-dione 

Downstream Products

• 444020-09-1 1-(3-deoxy-3-C-methyl-β-D-arabinofuranosyl)cytosine 

Relevant academic research and scientific papers

2’-Derivatisation of 3’-C-Methyl Pyrimidine Nucleosides

The stereoselective synthesis of some 3’-deoxy-3’-C-methyl pyrimidine nucleosides is reported. The studied modifications concern the inversion of the configuration in 2’-position as well as the introduction of fluoro and azido substituents. The correspond

Revisited 3′-deoxy-3′-C-methyl-β-D-ribonucleoside series

The synthesis of some 3′-deoxy-3′-C-methylnucleoside analogues bearing naturally occuring nucleic acid bases was achieved from the preparation of a suitable peracylated 3-deoxy-3-C-methyl sugar using a stereoselective pathway. In addition, examples of chemical modifications at the 2′ position are presented. Copyright Taylor & Francis Group, LLC.

Synthesis of 3′-deoxy-3′-C-methyl-β-d-ribonucleoside analogs

3′-Deoxy-3′-C-methyl-β-d-ribonucleoside analogs bearing the five canonical bases of nucleic acids have been synthesized. All these derivatives were prepared by glycosylation of the corresponding heterocyclic bases with a suitable peracylated 3-C-methyl su

Reactivity of 2',3'-anhydro pyrimidine nucleosides toward trimethylaluminum

Treatment of 2',3'-anhydro pyrimidine nucleoside derivatives (1) with trimethylaluminum afforded 1-(3-deoxy-3-methyl-β-D- arabinofuranosyl)pyrimidine derivatives (2) and 1-(2-deoxy-2-methyl-β-D- xylofuranosyl)pyrimidine derivatives (3) as a mixture in approximately 2 : 1 - 3 : 1 ratio via ring-opening of the epoxide involving the nucleophilic attack of trimethylaluminum at the 3' or 2'-position of 1.

1-(2,3-anhydro-β-D-lyxofuranosyl)cytosine derivatives as potential inhibitors of the human immunodeficiency virus

We report here that 1-(2,3-anhydro-β-D-lyxofuranosyl)cytosine has activity against the human immunodeficiency virus in vitro. A number of 2',3'-anhydro-β-D-lyxofuranosyl nucleoside derivatives were prepared, but none had the activity of the title compound. New efficient procedures were developed for the synthesis of 3'-deoxy-3'-alkyl- and 3'-deoxy-β-D-arabinosylpyrimidine derivatives.