Uses
1-(2'-Deoxy-2'-fluoro-b-D-arabinofuranosyl)cytosine HCl is a useful research chemical.
Uses
2’-Deoxy-2’-fluoro-b-D-arabinocytidine 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].
Synthesis
General procedure for the synthesis of 4-amino-1-(2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-2(1H)-pyrimidinone: 4-amino-1-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-beta-D-arabinofuranosyl)-2(1H)-pyrimidinone (3.60 mmol) was dissolved in saturated ammonia methanol solution (30 mL ) in saturated ammonia methanol solution (30 mL) and the reaction was stirred at room temperature for 15 hours. After completion of the reaction, the solvent was removed by concentration under reduced pressure to obtain the crude product. 5.64 (dd, J = 19.44 Hz, 1H, H-3'), 5.26 (d, J = 48.2 Hz, 1H, H-2'), 4.50 (m, 1H, H-4'), 3.70-3.77 (m, 2H, H-5').
References
[1] Robak T, Robak P. Purine nucleoside analogs in the treatment of rarer chronic lymphoid leukemias. Curr Pharm Des. 2012;18(23):3373-88. DOI:
10.2174/138161212801227005[2] SHINJI MIURA . Antitumor activity of a novel orally effective nucleoside, 1-(2-deoxy-2-fluoro-4-thio-β-d-arabinofuranosyl)cytosine[J]. Cancer letters, 1998, 129 1: Pages 103-110. DOI:
10.1016/s0304-3835(98)00089-5[3] J. A. MARTIN. ChemInform Abstract: Synthesis and Antiviral Activity of Monofluoro and Difluoro Analogues of Pyrimidine Deoxyribonucleosides Against Human Immunodeficiency Virus (HIV-1).[J]. ChemInform, 1991, 22 4. DOI:
10.1002/chin.199104325[4] KYOICHI A. WATANABE. Nucleosides. 123. Synthesis of antiviral nucleosides: 5-substituted 1-(2-deoxy-2-halogeno-.beta.-D-arabinofuranosyl)cytosines and -uracils. Some structure-activity relationships[J]. Journal of Medicinal Chemistry, 1983, 26 2: 152-156. DOI:
10.1021/jm00356a007
