25406-44-4

Basic information

• Product Name: Cytidine, 2'-deoxy-N,5-dimethyl-
• Synonyms: Cytidine, 2'-deoxy-N,5-dimethyl-;2'-deoxy-N,5-dimethylCytidine;N4-Methylthymidine
• CAS NO: 25406-44-4
• Molecular Formula: C11H17N3O4
• Molecular Weight: 255.272
• Mol File: 25406-44-4.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Cytidine, 2'-deoxy-N,5-dimethyl-(CAS DataBase Reference)
• NIST Chemistry Reference: Cytidine, 2'-deoxy-N,5-dimethyl-(25406-44-4)
• EPA Substance Registry System: Cytidine, 2'-deoxy-N,5-dimethyl-(25406-44-4)

Safety Data

• Hazardous Substances Data: 25406-44-4(Hazardous Substances Data)

Usage

Uses

N4,5-Dimethyldeoxycytidine has been shown to participate in cytidine deaminase inhibition.

Upstream product

• 40733-26-4 3',5'-O-di(tert-butyldimethylsilyl)thymidine 
• 35898-30-7 3',5'-di-O-benzoylthymidine 
• 20188-74-3 3',5'-di-O-acetyl-4-thiothymidine 
• 10457-18-8 3',5'-bis-O-(trimethylsilyl)-thymidine 
• 50-89-5 thymidine 
• 109389-25-5 1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methyl-4-(1H-1,2,4-triazol-1-yl)pyrimidin-2(1H)-one 
• 74-89-5 methylamine 
• 93841-35-1 O^3'_,O5'-dibenzoyl-4-thio-thymidine 

Relevant articles and documents

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).

Transformations of thiopyrimidine and thiopurine nucleosides following oxidation with dimethyldioxirane

A general and convenient method for the synthesis of several pyrimidine and purine nucleosides by selective oxidation of thionucleosides with dimethyldioxirane is reported. Thioketo moieties in the C-4 position of the pyrimidine ring, and in the C-6, and C-8 positions of the purine ring are the domain of oxidative nucleophilic substitution. Thioketo moieties in the C-2 position of both purine and pyrimidine rings are the domain of desulfurization or formation of disulfides.