M5628
6-Mercaptopurine-2′-deoxyriboside
Synonym(s):
2′-Deoxy-6-thioinosine, dI6S
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About This Item
Empirical Formula (Hill Notation):
C10H12N4O3S
CAS Number:
Molecular Weight:
268.29
UNSPSC Code:
41106305
PubChem Substance ID:
MDL number:
InChI
1S/C10H12N4O3S/c15-2-6-5(16)1-7(17-6)14-4-13-8-9(14)11-3-12-10(8)18/h3-7,15-16H,1-2H2,(H,11,12,18)
SMILES string
OCC1OC(CC1O)n2cnc3C(=S)N=CNc23
InChI key
WACLJMMBCDNRJE-UHFFFAOYSA-N
assay
≥98% (TLC)
form
powder
solubility
1 M NaOH: 50 mg/mL, clear, colorless to light yellow
storage temp.
−20°C
Biochem/physiol Actions
6-Mercaptopurine-2′-deoxyriboside (2′-deoxy-6-thioinosine; dI6S) is a thiolated inosine deoxynucleoside that may possess antitumor activity.
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Synthetic nucleosides and nucleotides. XIV. Facile synthesis and antitumor activities of 6-mercaptopurine 2'-deoxyriboside and related compounds.
M Saneyoshi et al.
Journal of pharmacobio-dynamics, 3(2), 105-110 (1980-02-01)
Christine Beuck et al.
Nucleosides, nucleotides & nucleic acids, 22(5-8), 635-639 (2003-10-21)
A facile synthesis of oligodeoxynucleotides (ODN) containing 2'-deoxy-6-thioinosine (dI6S) based on the convertible nucleoside O6-phenyl-2'-deoxyinosine is presented. After standard solid-phase DNA synthesis and removal of the cyanoethyl protecting groups with DBU treatment with aqueous sodium hydrogen sulfide introduces the sulfur
T A Krenitsky et al.
Journal of medicinal chemistry, 32(7), 1471-1475 (1989-07-01)
Azathioprine [Imuran; 6-[(1-methyl-4-nitro-1H-imidazol-5-yl)thio]-1H-purine] is a widely used immunosuppressive and antiarthritic drug. For the sake of comparison, the riboside, the 2'-deoxyriboside, and the arabinoside of azathioprine and its 2-amino congener, thiamiprine, were prepared by an enzymatic method. In vitro, the cytotoxicities
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