25406-45-5

Usage

Uses

Used in Pharmaceutical Industry:
Cytidine, 2'-deoxy-N,N,5-trimethylis used as a key intermediate in the synthetic preparation of antiviral pyrimidine nucleosides for the development of antiviral drugs. These nucleosides are particularly active against HIV-1 and HIV-2, making them valuable in the fight against these viral infections.
Used in Antiviral Research:
In the field of antiviral research, Cytidine, 2'-deoxy-N,N,5-trimethylserves as a starting material for the synthesis of novel antiviral compounds. These compounds can be tested for their effectiveness in inhibiting viral replication and preventing the spread of diseases caused by HIV-1 and HIV-2.
Used in Drug Development:
Cytidine, 2'-deoxy-N,N,5-trimethylis used as a building block in the development of new antiviral drugs. Its unique structure allows for the creation of innovative drug candidates that can potentially overcome drug resistance and improve the treatment of HIV-related conditions.

Upstream product

• 40733-26-4 3',5'-O-di(tert-butyldimethylsilyl)thymidine 
• 1107614-92-5 3’,5’-di-O-(t-butyldimethylsilyl)-N,N,5-trimethyl-2’-deoxycytidine 

Relevant academic research and scientific papers

The pH effect on the naphthoquinone-photosensitized oxidation of 5-methylcytosine

The pH effect on the one-electron photooxidation of 5-methyl-2′- deoxycytidine (dmC) by sensitization with 2-methyl-1,4-naphthoquinone (NQ) was investigated. Photoirradiation of an aqueous solution containing dmC and NQ under slightly acidic conditions of pH 5.0 efficiently produced 5-formyl-2′-deoxycytidine, whereas similar NQ-photosensitized oxidation of dmC proceeded to a lesser extent under more acidic or basic conditions. Fluorescence-quenching experiments re vealed that the less-efficient photooxidation at pH values below 4.5 is attributed to the decreased rate of one-electron oxidation of dmC owing to protonation at the N(3)-position. The NQ-photosensitized oxidation of an N(4)-dimethyl-substituted dmC derivative under various pH conditions also sug gests that the pH change in the range of 5.0 to 8.0 may be responsible for a reversible deprotonation-protonation equilibrium at the N(4)-exocyclic amino group of the dmC radical cation. In accord with the photochemical reactivity of monomeric dmC, the 5-methylcytosine residue in oligodeoxynucleotides was oxidized efficiently by photoexcited NQ-tethered oligodeoxynucleotides under slightly acidic conditions to form an alkali-labile 5-formylcytosine residue.

Facile functionalization at the C4 position of pyrimidine nucleosides via amide group activation with (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and biological evaluations of the products

Reactions of O-t-butyldimethylsilyl-protected thymidine, 2′-deoxyuridine, and 3′-azidothymidine (AZT) with (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) leads to activation of the C4 amide carbonyl by formation of putative O4-(benzotriazol-1-yl) derivatives. Subsequent substitution with alkyl and aryl amines, thiols, and alcohols leads to facile functionalization at this position. Reactions with amines and thiols were conducted either as a two-step, one-pot transformation, or as a one-step conversion. Reactions with alcohols were conducted as two-step, one-pot transformations. In the course of these investigations, the formation of 1-(4-pyrimidinyl)-1H-benzotriazole-3-oxide derivatives from the pyrimidine nucleosides was identified. However, these too underwent conversion to the desired products. Products obtained from AZT were converted to the 3′-amino derivatives by catalytic reduction. All products were assayed for their abilities to inhibit cancer cell proliferation and for antiviral activities. Many were seen to be active against HIV-1 and HIV-2, and one was active against herpes simplex virus-1 (HSV-1).