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5-(6-Aminopurin-9-yl)-2-(azidomethyl)oxolan-3-ol

HCID 3901376
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Basic information

CAS
42204-43-3
Standard SMILES
[N-]=[N+]=NCC1OC(n2cnc3c(N)ncnc32)CC1O
InChIKey
GCTRYQSKALFXJD-UHFFFAOYSA-N
Molecular formula
C10H12N8O2
Average molar mass
276.26 g/mol
Monoisotopic mass
276.10832166

Names & identifiers

Preferred name
5-(6-Aminopurin-9-yl)-2-(azidomethyl)oxolan-3-ol
IUPAC
5-(6-aminopurin-9-yl)-2-(azidomethyl)oxolan-3-ol
English name
[5-(6-aminopurin-9-yl)-3-hydroxy-oxolan-2-yl]methylimino-imino-azanium
Molecular formula
C10H15N8O2+
Molecular weight
279.2785

Names & synonyms

5-(6-aminopurin-9-yl)-2-(azidomethyl)oxolan-3-ol9-(5-Azido-2,5-dideoxypentofuranosyl)-9H-purin-6-amineDTXSID30962369NSC119843NSC-119843[5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methylimino-iminoazanium5’-Azido-2’,5’-dideoxyadenosine5'-Azido-2',5'-dideoxyadenosine[5-(6-aminopurin-9-yl)-3-hydroxy-oxolan-2-yl]methylimino-imino-azanium

Database identifiers

CAS
42204-43-3
PubChem CID
3901376
DTXSID
DTXSID30962369

Properties

Computed structural properties

XLogP
0.5
Topological polar surface area
113 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
8
Rotatable bonds
3
Heavy atoms
20
Formal charge
0
Complexity
403

Physicochemical properties

Melting point
78 · 78-79 °C (decomp)

Chemistry & industry

Applications · 1 item

Uses5′-Azido-2′,5′-dideoxyadenosine is a purine nucleoside analog. Purine nucleoside analogs have broad antitumor activity targeting indolent lymphoid malignancies. Anticancer mechanisms in this process rely on inhibition of DNA synthesis, induction of apoptosis, etc[1]. 5′-Azido-2′,5′-dideoxyadenosine 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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