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Novel potential anticancer naphthyl phosphoramidates of BVdU: Separation of diastereoisomers and assignment of the absolute cConfiguration of the phosphorus center

Congiatu, Costantino, Brancale, Andrea, Mason, Malcolm David, Jiang, Wen Guo and McGuigan, Christopher 2006. Novel potential anticancer naphthyl phosphoramidates of BVdU: Separation of diastereoisomers and assignment of the absolute cConfiguration of the phosphorus center. Journal of Medicinal Chemistry 49 (2) , pp. 452-455. 10.1021/jm0509896

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Abstract

We have previously reported our SAR optimization of the anticancer agent thymectacin. Tuning of the parent ProTide structure initially involved the amino acid and, subsequently, the aromatic masking group on the phosphate moiety. Herein, derivatives bearing the combined modifications are reported and biological evaluation is described. Moreover, separation of the diastereoisomeric final product mixture shows a different cytostatic activity for the two diastereoisomers. Through computational and NMR studies, the absolute stereochemistry of the phosphorus center of the two diastereoisomers has been suggested.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Medicine
Pharmacy
Systems Immunity Research Institute (SIURI)
Subjects: R Medicine > RC Internal medicine > RC0254 Neoplasms. Tumors. Oncology (including Cancer)
R Medicine > RS Pharmacy and materia medica
ISSN: 0022-2623
Last Modified: 18 Oct 2017 13:43
URI: http://orca-mwe.cf.ac.uk/id/eprint/7446

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