PubMed · 14210423
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K STACH, O DOLD. 1963. [NEW CENTRALLY-ACTING, BASIC ESTERS. 2. GRANATANOL-3-ESTERS].. https://pubmed.ncbi.nlm.nih.gov/14210423/
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A synthesis of 2-epi-amphidinolide E (1) has been accomplished via an unexpected and highly diastereoselective C(2) stereochemical inversion during the modified Yamaguchi esterification of alcohol 4b and Fe(CO)3-complexed dienoic acid 7. [reaction: see text].
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A series of novel, multisubstrate, bicyclic pyrimidine nucleoside inhibitors of human thymidine phosphorylase (TP) is described. Thymidine phosphorylase has been implicated in angiogenesis and plays a significant role in tumor progression and metastasis. The presence and orientation of the phosphonate moiety (acting as a phosphate mimic) in these derivatives were critical for inhibitory activity. The most active compounds possessed a phosphonate group in an endo orientation. This was consistent with molecular modeling results that showed the endo isomer protein-ligand complex to be lower in energy than the exo complex.