4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine

Product Name: 4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine
CAS No.: 1011529-10-4
Chemical Name: 4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine
Synonyms: Azvudine;FNC;RO 0622;Azvudine (RO 0622);Azvudine, 10 mM in DMSO;Eravacycline Impurity 9;4'-Azido-2'-deoxy-2'-fluoroaracytidine;4′-azido-2′-deoxy-2′-fluoro-β-D-arabinocytidine;4’-Azido-2’-deoxy-2’-fluoroaracytidine, Azvudine;4'-C-Azido-2'-deoxy-2'-fluoro-b-D-arabinocytidine
CBNumber: CB02641492
Molecular Formula: C9H11FN6O4
Formula Weight: 286.2198432
MOL File: 1011529-10-4.mol

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4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine Property

Melting point:: 99.0-100.0℃
storage temp.: Store at -20°C
solubility: DMSO: 57 mg/mL (199.15 mM);Ethanol: 57 mg/mL (199.15 mM)
form: Solid
color: White to off-white
Water Solubility: Water: 57 mg/mL (199.15 mM)
InChI: InChI=1/C9H11FN6O4/c10-5-6(18)9(3-17,14-15-12)20-7(5)16-2-1-4(11)13-8(16)19/h1-2,5-7,17-18H,3H2,(H2,11,13,19)/t5-,6-,7+,9+/s3
InChIKey: KTOLOIKYVCHRJW-BODDTQOYNA-N
SMILES: C1(=O)N([C@H]2[C@@H](F)[C@H](O)[C@@](N=[N+]=[N-])(CO)O2)C=CC(N)=N1 |&1:3,4,6,8,r|

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Biosynth Carbosynth

Product number: NA32212
Product name: 4'-C-Azido-2'-deoxy-2'-fluoro-b-D-arabinocytidine
Packaging: 250ug
Price: $75
Updated: 2021/12/16

Biosynth Carbosynth

Product number: NA32212
Product name: 4'-C-Azido-2'-deoxy-2'-fluoro-b-D-arabinocytidine
Packaging: 500ug
Price: $125
Updated: 2021/12/16

Biosynth Carbosynth

Product number: NA32212
Product name: 4'-C-Azido-2'-deoxy-2'-fluoro-b-D-arabinocytidine
Packaging: 1mg
Price: $225
Updated: 2021/12/16

Biosynth Carbosynth

Product number: NA32212
Product name: 4'-C-Azido-2'-deoxy-2'-fluoro-b-D-arabinocytidine
Packaging: 2mg
Price: $350
Updated: 2021/12/16

AK Scientific

Product number: 0448EP
Product name: 4-Amino-1-[(5R)-5-azido-3-fluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
Packaging: 2mg
Price: $522
Updated: 2021/12/16

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4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine Chemical Properties,Usage,Production

Description

Azvudine is an antiviral drug produced by Genuine Biotech and was approved in China in 2021 as a first-in-class drug for the treatment of human immunodeficiency virus (HIV).

Uses

Azvudine (RO-0622) is a potent nucleoside reverse transcriptase inhibitor (NRTI), with antiviral activity on HIV, HBV and HCV. Azvudine exerts highly potent inhibition on HIV-1 (EC50s ranging from 0.03 to 6.92 nM) and HIV-2 (EC50s ranging from 0.018 to 0.025 nM). Azvudine inhibits NRTI-resistant viral strains[1]. Azvudine 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.

Application

Azvudine has also been repurposed as a treatment for COVID-19 and was approved in China in 2022 as an RNA-dependent RNA polymerase (RdRp) inhibitor, sharing the same mechanism as the previously approved molnupiravir and remdesivir. In addition to its antiviral activity, the drug's concentration in the thymus suggests that it may also have immune-targeting activity, which is unique among RdRp inhibitors.

Mechanism of action

Azvudine has a dual mechanism of action: it acts as a reverse transcriptase inhibitor and targets the viral factor/apolipoprotein B mRNA editing enzyme, catalytic subunit 3G (Vif/A3G) protein-protein interaction. Due to substitutions at its 3′-hydroxyl and 4′-ribose core, azithromycin is active against both wild-type and resistant strains of HIV.

Synthesis

The synthesis is carried out starting from benzoyl protected fluorofuranose 1.1. Bromination with HBr in acetic acid followed by displacement of bromide 1.2 with protected cytosine 1.3 gives intermediate 1.4. Deprotection of the benzoyl group with ammonia in methanol gives diol 1.5, which is then converted to the alkyl iodide 1.6 via a Mitsunobu reaction. Elimination of iodine with sodium methoxide followed by addition of sodium azide and iodine chloride to the resulting olefin gives azide 1.7. Both the alcohol and amine are reprotected with benzoyl chloride, and the iodine is displaced by m-chlorobenzoic acid in an oxidative nucleophilic substitution reaction to give the penultimate intermediate 1.9. All protecting groups are then removed in methanol-ammonia to give azithromycin (1).

IC 50

HIV-1: 0.03-6.92 nM (EC₅₀); HIV-2: 0.018-0.02 nM (EC₅₀)

References

[1] Wang RR, et al. Azvudine, a novel nucleoside reverse transcriptase inhibitor showed good drug combination features and better inhibition on drug-resistant strains than lamivudine in vitro. PLoS One. 2014 Aug 21;9(8):e105617. DOI:10.1371/journal.pone.0105617

4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine Preparation Products And Raw materials

Raw materials

Preparation Products

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4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine Suppliers

China 77 United States 7 Global 84

TargetMol Chemicals Inc.

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View Lastest Price from 4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine manufacturers

ShenZhen H&D Pharmaceutical Technology Co., LTD

Product: Eravacycline Impurity 9
Price: US $0.00/mg
Min. Order: 10mg
Purity: 0.98
Supply Ability: 5g
Release date: 2025-03-21

Hangzhou ICH Biofarm Co., Ltd

Product: 4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine 1011529-10-4
Price: US $0.00-0.00/g
Min. Order: 1g
Purity: 98% HPLC
Supply Ability: 100kg
Release date: 2023-07-05

Hangzhou ICH Biofarm Co., Ltd

Product: 4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine 1011529-10-4
Price: US $0.00-0.00/g
Min. Order: 1g
Purity: 98% HPLC
Supply Ability: 100kg
Release date: 2023-07-05

1011529-10-4, 4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidineRelated Search:

4'-C-azido-2'-deoxy-2'-fluoro-beta-D-arabinocytidine

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4'-C-Azido-2'-deoxy-2'-fluoro-b-D-arabinocytidine

4'-Azido-2'-deoxy-2'-fluoroaracytidine

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4’-Azido-2’-deoxy-2’-fluoroaracytidine, Azvudine

4′-azido-2′-deoxy-2′-fluoro-β-D-arabinocytidine

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4'-C-Azido-2'-deoxy-2'-fluoro-β-D-arabinocytidine

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Azvudine, 10 mM in DMSO

1011529-10-4

C9H11FN6O4

1011529-10-4