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Design, synthesis, and biological evaluation of C1-phosphonamidate analogues of 2-deoxy-d-ribose-1-phosphate

Quintiliani, Maurizio, Balzarini, Jan and McGuigan, Christopher 2013. Design, synthesis, and biological evaluation of C1-phosphonamidate analogues of 2-deoxy-d-ribose-1-phosphate. Tetrahedron 69 (43) , pp. 9111-9119. 10.1016/j.tet.2013.08.038

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Abstract

A novel series of phenoxy C1–phosphonamidate derivatives of 2-deoxy-d-ribose have been synthesised as stable analogues of 2-deoxy-α-d-ribose-1-phosphate. A number of synthetic routes were explored for the preparation of these targets. The successful approach involved the synthesis of a protected C1–phosphonate ester 17 via Michaelis–Arbuzov reaction, which was then hydrolysed and coupled with different amino acid esters using aldrithiol. Subsequent hydrogenolysis afforded the targets 2a–g, which were isolated as a mixture of diastereoisomers. The compounds were assayed for inhibition of thymidine phosphorylase (TP) and uridine phosphorylase (UP) and for antiviral and cytostatic activity.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Pharmacy
Systems Immunity Research Institute (SIURI)
Subjects: R Medicine > RM Therapeutics. Pharmacology
Uncontrolled Keywords: Deoxyribose; Phosphorylation; Phosphonates; Phosphonamidates
Publisher: Elsevier
ISSN: 0040-4020
Last Modified: 16 Oct 2017 21:04
URI: http://orca.cf.ac.uk/id/eprint/53044

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