98983-40-5

Usage

Uses

Used in Oncology:
9-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-1,9-dihydro-6H-purin-6-one is utilized as a therapeutic agent for the treatment of hematological malignancies, such as chronic lymphocytic leukemia (CLL) and non-Hodgkin's lymphoma. Its mechanism of action involves the interference with DNA synthesis, leading to the cessation of cancer cell growth and ultimately causing cell death.
Used in Pharmaceutical Formulations:
9-(2-Deoxy-2-fluoro-beta-D-arabinofuranosyl)-1,9-dihydro-6H-purin-6-one is typically administered through injection or intravenous infusion, making it a key component in the formulation of antineoplastic drugs. The pharmaceutical industry relies on its potent activity against certain types of cancer, despite the potential for adverse side effects such as bone marrow suppression and neurological complications.

InChI:InChI=1/C10H11FN4O4/c11-5-7(17)4(1-16)19-10(5)15-3-14-6-8(15)12-2-13-9(6)18/h2-5,7,10,16-17H,1H2,(H,12,13,18)/t4-,5+,7-,10-/m1/s1

Upstream product

• 20187-82-0 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)adenine 
• 4005-49-6 N-benzoyladenine 
• 68-94-0 hypoxanthine 
• 109303-87-9 9-(3-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-β-D-arabinofuranosyl)-N⁶-benzoyladenine 
• 56632-81-6 1,3-di-O-acetyl-5-O-benzoyl-2-deoxy-2-fluoro-D-arabinofuranosyl bromide 
• 136852-40-9 9-(2-Deoxy-2-fluoro-3,5-di-O-trityl-β-D-arabinofuranosyl)-1-benzylinosine 

Relevant academic research and scientific papers

The chemoenzymatic synthesis of clofarabine and related 2′-deoxyfluoroarabinosyl nucleosides: The electronic and stereochemical factors determining substrate recognition by E. coli nucleoside phosphorylases

Two approaches to the synthesis of 2-chloro-9-(2-deoxy-2-fluoro-β-D- arabinofuranosyl)adenine (1, clofarabine) were studied. The first approach consists in the chemical synthesis of 2-deoxy-2-fluoro-α-D- arabinofuranose-1-phosphate (12a, 2FAra-1P) via three step conversion of 1,3,5-tri-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranose (9) into the phosphate 12a without isolation of intermediary products. Condensation of 12a with 2-chloroadenine catalyzed by the recombinant E. coli purine nucleoside phosphorylase (PNP) resulted in the formation of clofarabine in 67% yield. The reaction was also studied with a number of purine bases (2-aminoadenine and hypoxanthine), their analogues (5-aza-7-deazaguanine and 8-aza-7- deazahypoxanthine) and thymine. The results were compared with those of a similar reaction with α-D-arabinofuranose-1-phosphate (13a, Ara-1P). Differences of the reactivity of various substrates were analyzed by ab initio calculations in terms of the electronic structure (natural purines vs analogues) and stereochemical features (2FAra-1P vs Ara-1P) of the studied compounds to determine the substrate recognition by E. coli nucleoside phosphorylases. The second approach starts with the cascade one-pot enzymatic transformation of 2-deoxy-2-fluoro-D-arabinose into the phosphate 12a, followed by its condensation with 2-chloroadenine thereby affording clofarabine in ca. 48% yield in 24 h. The following recombinant E. coli enzymes catalyze the sequential conversion of 2-deoxy-2-fluoro-D-arabinose into the phosphate 12a: ribokinase (2-deoxy-2-fluoro-D-arabinofuranose-5-phosphate), phosphopentomutase (PPN; no 1,6-diphosphates of D-hexoses as co-factors required) (12a), and finally PNP. The substrate activities of D-arabinose, D-ribose and D-xylose in the similar cascade syntheses of the relevant 2-chloroadenine nucleosides were studied and compared with the activities of 2-deoxy-2-fluoro-D-arabinose. As expected, D-ribose exhibited the best substrate activity [90% yield of 2-chloroadenosine (8) in 30 min], D-arabinose reached an equilibrium at a concentration of ca. 1:1 of a starting base and the formed 2-chloro-9-(β-D- arabinofuranosyl) adenine (6) in 45 min, the formation of 2-chloro-9-(β-D- xylofuranosyl)adenine (7) proceeded very slowly attaining ca. 8% yield in 48 h.