1373400-34-0

Basic information

• Product Name: (-)-5'-O-(12-aminododecanoyl)-N⁽⁴⁾-(4,4'-dimethoxytrityl)-2',3'-dideoxy-3'-thiacytidine
• Synonyms: (-)-5'-O-(12-aminododecanoyl)-N⁽⁴⁾-(4,4'-dimethoxytrityl)-2',3'-dideoxy-3'-thiacytidine
• CAS NO: 1373400-34-0
• Molecular Weight: 728.953
• Mol File: 1373400-34-0.mol

Chemical Properties

• CAS DataBase Reference: (-)-5'-O-(12-aminododecanoyl)-N⁽⁴⁾-(4,4'-dimethoxytrityl)-2',3'-dideoxy-3'-thiacytidine(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-5'-O-(12-aminododecanoyl)-N⁽⁴⁾-(4,4'-dimethoxytrityl)-2',3'-dideoxy-3'-thiacytidine(1373400-34-0)
• EPA Substance Registry System: (-)-5'-O-(12-aminododecanoyl)-N⁽⁴⁾-(4,4'-dimethoxytrityl)-2',3'-dideoxy-3'-thiacytidine(1373400-34-0)

Safety Data

• Hazardous Substances Data: 1373400-34-0(Hazardous Substances Data)

Upstream product

• 134678-17-4 lamivudine 
• 956896-97-2 (-)-5'-O-(t-butyldimethylsilyl)-2',3'-dideoxy-3'-thiacytidine 
• 1373400-32-8 (-)-5'-O-(12-(N-Fmoc-aminododecanoyl))-N⁽⁴⁾-(4,4'-dimethoxytrityl)-2',3'-dideoxy-3'-thiacytidine 
• 956896-99-4 (-)-5'-O-(t-butyldimethylsilyl)-N⁽⁴⁾-(4,4'-dimethoxytrityl)-2',3'-dideoxy-3'-thiacytidine 
• 956897-01-1 (-)-N⁽⁴⁾-(4,4'-dimethoxytrityl)-2',3'-dideoxy-3'-thiacytidine 
• 128917-74-8 9-fluorenylmethoxycarbonyl-12-aminododecanoic acid 

Relevant articles and documents

Synthesis and biological evaluation of fatty acyl ester derivatives of (-)-2′,3′-dideoxy-3′-thiacytidine

A number of fatty acyl derivatives of (-)-2′,3′-dideoxy- 3′-thiacytidine (lamivudine, 3TC, 1) were synthesized and evaluated for their anti-HIV activity. The monosubstituted 5′-O-fatty acyl derivatives of 3TC (EC50 = 0.2-2.3 μM) were more potent than the corresponding monosubstituted N4-fatty acyl (EC50 = 0.4-29.4 μM) and 5′-O-N4-disubstituted (EC50 = 72.6 to >154.0 μM) derivatives of the nucleoside. 5′-O-Myristoyl (16) and 5′-O-12-azidododecanoyl derivatives (17) were found to be the most potent compounds (EC50 = 0.2-0.9 μM) exhibiting at least 16-36-fold higher anti-HIV activity against cell-free virus than 1 (EC50 = 11.4-32.7 μM). The EC90 values for 16 against B-subtype and C-subtype clinical isolates were several folds lower than those of 1. The cellular uptake studies confirmed that compound 16 accumulated intracellularly after 1 h of incubation with CCRF-CEM cells and underwent intracellular hydrolysis. 5′-O-Fatty acyl derivatives of 1 showed significantly higher anti-HIV activity than the corresponding physical mixtures against the B-subtype virus.