Mitsunobu Alkylation of Cancerostatic 5-Fluorouridine with (2E)-10-Hydroxydec-2-enoic Acid, a Fatty Acid from Royal Jelly with Multiple Biological Activities
| Autor(en): | Ottenhaus, Vanessa Rosemeyer, Helmut |
Stichwörter: | 5-FLUORO-2'-DEOXYURIDINE; Biochemistry & Molecular Biology; BIOMIMETIC LIPOPHILIZATION; Chemistry; Chemistry, Multidisciplinary; CYTOSTATIC 5-FLUOROURIDINE; DRUG DISCOVERY; FTORAFUR; IN-VITRO; NUCLEIC-ACIDS; OLIGONUCLEOTIDES; THYMIDINE; TUMORS | Erscheinungsdatum: | 2015 | Herausgeber: | WILEY-V C H VERLAG GMBH | Journal: | CHEMISTRY & BIODIVERSITY | Volumen: | 12 | Ausgabe: | 9 | Startseite: | 1307 | Seitenende: | 1312 | Zusammenfassung: | 5-Fluorouridine (1) - a nucleoside antimetabolite with strong cancerostatic properties - was protected i) at the 2'-and 3'-OH groups with a heptan-4-ylidene residue and ii) at the 5'-OH group with a (4-methoxyphenyl)(diphenyl) methyl residue. This fully protected compound, 3, was submitted to a Mitsunobu reaction with the N-hydroxysuccinimide (NHS) ester, 5, of (2E)-10-hydroxydec-2-enoic acid (4) which gave nucleolipid 6. The latter was detritylated with Cl2CHCOOH to yield the co-drug 7 as NHS ester. |
ISSN: | 16121872 | DOI: | 10.1002/cbdv.201500048 |
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