2-THIOADENOSINE Chemical Properties

Melting point:

>178°C (dec.)

Boiling point:

544.5±60.0 °C(Predicted)

Density 

2.18±0.1 g/cm3(Predicted)

storage temp. 

2-8°C(protect from light)

solubility 

Aqueous Base (Slightly), DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)

form 

Solid

pka

8.37±0.40(Predicted)

color 

Pale Yellow to Yellow

InChI

InChI=1S/C10H13N5O4S/c11-7-4-8(14-10(20)13-7)15(2-12-4)9-6(18)5(17)3(1-16)19-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,20)/t3-,5-,6-,9-/m1/s1

InChIKey

LTESOZAUMTUKQX-UUOKFMHZSA-N

SMILES

OC[C@H]1O[C@@H](N2C3=C(C(=NC(=S)N3)N)N=C2)[C@H](O)[C@@H]1O

CAS DataBase Reference

43157-50-2

Safety Information

HS Code 

2934999090

2-THIOADENOSINE Usage And Synthesis

Description

2-Thioadenosine is a pharmaceutical intermediate compound used in the preparation of cangrelor, a P2Y12 platelet receptor antagonist used to prevent or reduce the risk of thrombosis during stenting procedures. In biology, it regulates the synthesis and degradation of important biomolecules such as DNA, RNA and proteins. It also regulates cell signalling pathways, including those involved in cell growth, proliferation and apoptosis. In addition, it plays a role in maintaining cellular redox balance and regulating oxidative stress.

Uses

2-Thioadenosine has application for developing platelet aggregation inhibitors.

Application

Intermediate in the synthesis of cangrelor

Synthesis

General procedure for the synthesis of 6-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3,9-dihydro-2H-purine-2-thione from carbon disulfide and the compound (CAS: 57004-06-5): In a reaction flask, tetrahydrofuran (5 mL), the compound (II) (27 g. 100 mmol), methanol (100 mL), carbon disulfide (100 mL) and dimethyl sulfoxide (500 mL) and mixed with thorough stirring. The reaction mixture was heated to 140-150 °C and the reaction was continuously stirred at this temperature for 12 hours. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The crude product was washed sequentially with ethanol and water, and then with saturated aqueous sodium chloride solution, and finally dried to give 24 g of the target product in 80% yield.

References

[1] Patent: CN105693800, 2016, A. Location in patent: Paragraph 0028; 0029
[2] Journal of Medicinal Chemistry, 2009, vol. 52, # 23, p. 7669 - 7677
[3] European Journal of Medicinal Chemistry, 2016, vol. 107, p. 204 - 218

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