1219808-60-2

Basic information

• Product Name: 1-((2R,4S,5S)-4-(4-(3,4-dichlorophenyl)-1H-1,2,3-triazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
• Synonyms: 1-((2R,4S,5S)-4-(4-(3,4-dichlorophenyl)-1H-1,2,3-triazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
• CAS NO: 1219808-60-2
• Molecular Weight: 438.27
• Mol File: 1219808-60-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 1-((2R,4S,5S)-4-(4-(3,4-dichlorophenyl)-1H-1,2,3-triazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 1-((2R,4S,5S)-4-(4-(3,4-dichlorophenyl)-1H-1,2,3-triazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione(1219808-60-2)
• EPA Substance Registry System: 1-((2R,4S,5S)-4-(4-(3,4-dichlorophenyl)-1H-1,2,3-triazol-1-yl)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione(1219808-60-2)

Safety Data

• Hazardous Substances Data: 1219808-60-2(Hazardous Substances Data)

Upstream product

• 30516-87-1 3'-azido-2',3'-deoxythymidine 
• 556112-20-0 3,4-dichlorophenylacetylene 

Relevant articles and documents

Clicking 3′-azidothymidine into novel potent inhibitors of human immunodeficiency virus

3′-Azidothymidine (AZT) was the first approved antiviral for the treatment of human immunodeficiency virus (HIV). Reported efforts in clicking the 3′-azido group of AZT have not yielded 1,2,3-triazoles active against HIV or any other viruses. We report herein the first AZT-derived 1,2,3-triazoles with submicromolar potencies against HIV-1. The observed antiviral activities from the cytopathic effect (CPE) based assay were confirmed through a single replication cycle assay. Structure-activity-relationship (SAR) studies revealed two structural features key to antiviral activity: a bulky aromatic ring and the 1,5-substitution pattern on the triazole. Biochemical analysis of the corresponding triphosphates showed lower ATP-mediated nucleotide excision efficiency compared to AZT, which along with molecular modeling suggests a mechanism of preferred translocation of triazoles into the P-site of HIV reverse transcriptase (RT). This mechanism is corroborated with the observed reduction of fold resistance of the triazole analogue to an AZT-resistant HIV variant (9-fold compared to 56-fold with AZT).