Mitsunobu Alkylation of Cancerostatic 5-Fluorouridine with (2E)-10-Hydroxydec-2-enoic Acid, a Fatty Acid from Royal Jelly with Multiple Biological Activities

DC ElementWertSprache
dc.contributor.authorOttenhaus, Vanessa
dc.contributor.authorRosemeyer, Helmut
dc.date.accessioned2021-12-23T16:00:29Z-
dc.date.available2021-12-23T16:00:29Z-
dc.date.issued2015
dc.identifier.issn16121872
dc.identifier.urihttps://osnascholar.ub.uni-osnabrueck.de/handle/unios/4422-
dc.description.abstract5-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.
dc.description.sponsorshipBBraun AG (Melsungen, Germany); Bundesministerium fur Wirtschaft [FKZ KF 2369401S B9, FKZ 2369501 S B9]; The authors gratefully acknowledge the financial support of the BBraun AG (Melsungen, Germany), as well as the Bundesministerium fur Wirtschaft (FKZ KF 2369401S B9 and FKZ 2369501 S B9). We thank Prof. Dr. Uwe Beginn (Organic Materials Chemistry, University of Osnabruck) for excellent laboratory facilities. Moreover, we thank Mrs. Marianne Gather-Steckhan for NMR spectra and Dr. Stefan Walter for ESI-MS.
dc.language.isoen
dc.publisherWILEY-V C H VERLAG GMBH
dc.relation.ispartofCHEMISTRY & BIODIVERSITY
dc.subject5-FLUORO-2'-DEOXYURIDINE
dc.subjectBiochemistry & Molecular Biology
dc.subjectBIOMIMETIC LIPOPHILIZATION
dc.subjectChemistry
dc.subjectChemistry, Multidisciplinary
dc.subjectCYTOSTATIC 5-FLUOROURIDINE
dc.subjectDRUG DISCOVERY
dc.subjectFTORAFUR
dc.subjectIN-VITRO
dc.subjectNUCLEIC-ACIDS
dc.subjectOLIGONUCLEOTIDES
dc.subjectTHYMIDINE
dc.subjectTUMORS
dc.titleMitsunobu Alkylation of Cancerostatic 5-Fluorouridine with (2E)-10-Hydroxydec-2-enoic Acid, a Fatty Acid from Royal Jelly with Multiple Biological Activities
dc.typejournal article
dc.identifier.doi10.1002/cbdv.201500048
dc.identifier.isiISI:000362820800002
dc.description.volume12
dc.description.issue9
dc.description.startpage1307
dc.description.endpage1312
dc.identifier.eissn16121880
dc.publisher.placePOSTFACH 101161, 69451 WEINHEIM, GERMANY
dcterms.isPartOf.abbreviationChem. Biodivers.
crisitem.author.deptInstitut für Chemie neuer Materialien-
crisitem.author.deptidinstitute11-
crisitem.author.parentorgFB 05 - Biologie/Chemie-
crisitem.author.grandparentorgUniversität Osnabrück-
crisitem.author.netidRoHe783-
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