CAS 26929-65-7

2′-Azido-2′-deoxyuridine

Description:

2′-Azido-2′-deoxyuridine (AZT) is a nucleoside analog of thymidine, characterized by the presence of an azido group at the 2′ position of the sugar moiety. This modification imparts unique properties that make it a significant compound in medicinal chemistry, particularly in antiviral therapies. AZT is primarily known for its role as an antiretroviral drug used in the treatment of HIV/AIDS, functioning as a reverse transcriptase inhibitor. Its mechanism involves incorporation into viral DNA, leading to chain termination during replication. The compound is typically administered in its phosphate form, which enhances its bioavailability and efficacy. AZT is soluble in water and exhibits moderate stability under physiological conditions, although it can be sensitive to light and heat. Its pharmacokinetics involve rapid absorption and distribution, with metabolism primarily occurring in the liver. While effective, AZT can also lead to side effects, including bone marrow suppression and mitochondrial toxicity, necessitating careful monitoring during treatment. Overall, 2′-Azido-2′-deoxyuridine represents a crucial advancement in antiviral therapy, showcasing the importance of nucleoside analogs in modern medicine.

Formula: C₉H₁₁N₅O₅

InChI: InChI=1S/C9H11N5O5/c10-13-12-6-7(17)4(3-15)19-8(6)14-2-1-5(16)11-9(14)18/h1-2,4,6-8,15,17H,3H2,(H,11,16,18)/t4-,6-,7-,8-/m1/s1

InChI key: InChIKey=MRUKYOQQKHNMFI-XVFCMESISA-N

SMILES: N(=[N+]=[N-])[C@H]1[C@@H](O[C@H](CO)[C@H]1O)N2C(=O)NC(=O)C=C2

Synonyms:

• 1-(2-azido-2-deoxypentofuranosyl)pyrimidine-2,4(1H,3H)-dione
• NSC 678533
• Uridine, 2′-azido-2′-deoxy-
• 2′-Azido-2′-deoxyuridine

2'-Azido-2'-deoxyuridine

CAS: 26929-65-7

Formula: C₉H₁₁N₅O₅

Purity: >98.0%(HPLC)

Color and Shape: White to Almost white powder to crystal

Molecular weight: 269.22

Ref: 3B-A2942

1-[(2R,3R,4S,5R)-3-azido-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

CAS: 26929-65-7

Formula: C₉H₁₁N₅O₅

Purity: 98%

Molecular weight: 269.2141

Ref: IN-DA00ILP6

2''-Azido-2''-deoxyuridine

CAS: 26929-65-7

Formula: C₉H₁₁N₅O₅

Molecular weight: 269.21

Ref: 7W-GN5404

2'-Azido-2'-deoxyuridine

CAS: 26929-65-7

2'-Azido-2'-deoxyuridine is a synthetic nucleoside analog of uridine in which the 2'-hydroxyl group on the ribose sugar is replaced with an azido group (–N₃), and the base is unmodified uracil. This modification alters the sugar's conformation and chemical reactivity, enabling the use of this analog in bioorthogonal labeling strategies, particularly through azide-alkyne "click" chemistry. Its incorporation into nucleic acids can influence polymerase recognition and chain elongation, making it a useful probe in studies of RNA synthesis, structure, and function.

Formula: C₉H₁₁N₅O₅

Purity: Min. 98 Area-%

Color and Shape: White Off-White Powder

Molecular weight: 269.21 g/mol

Ref: 3D-NA06303

2′-AZIDO-2′-DEOXYURIDINE

CAS: 26929-65-7

Formula: C₉H₁₁N₅O₅

Purity: ≥98%

Molecular weight: 269.217

Ref: 10-F334253

2'-Azido-2'-deoxyuridine

CAS: 26929-65-7

2'-Azido-2'-deoxyuridine (N3dUrd) is a ribonucleotide reductase inhibitor with anti-cancer activity.

Formula: C₉H₁₁N₅O₅

Purity: 98%

Color and Shape: Solid

Molecular weight: 269.21

Ref: TM-T10068