84472-85-5
Chemical Structure
3′-Azido-2′,3′-dideoxyuridine
Synonym(s): AzdU; AzddU; CS-87
- CAS No.: 84472-85-5
- Formula:C9H11N5O4
- Molecular Weight:253.21
IUPAC Name: 1-((2R,4S,5S)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
InChIKey: ZSNNBSPEFVIUDS-SHYZEUOFSA-N
SMILES: OC[C@H]([C@@H](N=[N+]=[N-])C1)O[C@H]1N(C=C2)C(NC2=O)=O
Biological Activity: 3′-Azido-2′,3′-dideoxyuridine (AzdU) is a nucleoside analog of Zidovudine (HY-17413). 3′-Azido-2′,3′-dideoxyuridine is a potent inhibitor of human immunodeficiency virus (HIV) replication in human peripheral blood mononuclear cells (PBMC) with limited toxicity for human bone marrow cells (BMC)[1][2][3]. 3′-Azido-2′,3′-dideoxyuridine is a click chemistry reagent, it contains an Azide group and can undergo copper-catalyzed azide-alkyne cycloaddition reaction (CuAAc) with molecules containing Alkyne groups. It can also undergo strain-promoted alkyne-azide cycloaddition (SPAAC) reactions with molecules containing DBCO or BCN groups.
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3′-Azido-2′,3′-dideoxyuridine | 99.59% | 3′-Azido-2′,3′-dideoxyuridine (AzdU) is a nucleoside analog of Zidovudine (HY-17413). 3′-Azido-2′,3′-dideoxyuridine is a potent inhibitor of human immunodeficiency virus (HIV) replication in human peripheral blood mononuclear cells (PBMC) with limited toxicity for human bone marrow cells (BMC). 3′-Azido-2′,3′-dideoxyuridine is a click chemistry reagent, it contains an Azide group and can undergo copper-catalyzed azide-alkyne cycloaddition reaction (CuAAc) with molecules containing Alkyne groups. It can also undergo strain-promoted alkyne-azide cycloaddition (SPAAC) reactions with molecules containing DBCO or BCN groups. | ||||||||||||||||||||
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References
- [1]. Zhu Z, et al. Cellular metabolism of 3'-azido-2',3'-dideoxyuridine with formation of 5'-O-diphosphohexose derivatives by previously unrecognized metabolic pathways for 2'-deoxyuridine analogs. Mol Pharmacol. 1990 Dec;38(6):929-38. [Content Brief]
- [2]. Chu CK, et al. Structure-activity relationships of pyrimidine nucleosides as antiviral agents for human immunodeficiency virus type 1 in peripheral blood mononuclear cells. J Med Chem. 1989 Mar;32(3):612-7. [Content Brief]
- [3]. Kong L, et al. Pharmacokinetic evaluation of 3'-azido-2', 3'-dideoxyuridine-5'-O-valinate-hydrochloride as a prodrug of the anti-HIV nucleoside 3'-azido-2', 3'-dideoxyuridine. Antivir Chem Chemother. 2003 Sep;14(5):263-70. [Content Brief]
