25406-45-5

Basic information

• Product Name: Cytidine, 2'-deoxy-N,N,5-trimethyl-
• Synonyms: Cytidine, 2'-deoxy-N,N,5-trimethyl-;4-dimethylaminothymidine;2'-deoxy-N,N,5-trimethylCytidine;N4,N4-Dimethylthymidine;2'-Deoxy-5,N4,N4-trimethylcytidine
• CAS NO: 25406-45-5
• Molecular Formula: C12H19N3O4
• Molecular Weight: 269.29696
• Mol File: 25406-45-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 457.3 °C at 760 mmHg
• Flash Point: 230.4 °C
• Appearance: /
• Density: 1.41 g/cm³
• CAS DataBase Reference: Cytidine, 2'-deoxy-N,N,5-trimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Cytidine, 2'-deoxy-N,N,5-trimethyl-(25406-45-5)
• EPA Substance Registry System: Cytidine, 2'-deoxy-N,N,5-trimethyl-(25406-45-5)

Safety Data

• Hazardous Substances Data: 25406-45-5(Hazardous Substances Data)

Usage

Description

Cytidine, 2'-deoxy-N,N,5-trimethylis a modified nucleoside derived from cytidine, with a 2'-deoxy sugar moiety and trimethylation at the N4 and N6 positions. This modification contributes to its unique properties and potential applications in various fields.

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

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

Relevant articles and documents

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.

Preparation and properties of N4-alkyl analogues of 5-methyl-2'-deoxycytidine, their 5'-mono- and triphosphates, and N4-alkyl derivatives of 1,5-dimethylcytosine.

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