Synthesis and in Vitro Cytotoxicity of Acetylated 3-Fluoro,4-Fluoro and 3,4-Difluoro Analogs of D-glucosamine and D-galactosamine.
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F67985858%3A_____%2F16%3A00458825" target="_blank" >RIV/67985858:_____/16:00458825 - isvavai.cz</a>
Alternative codes found
RIV/61388963:_____/16:00458825 RIV/00209805:_____/16:N0000027 RIV/00216208:11310/16:10324341
Result on the web
<a href="http://dx.doi.org/10.3762/bjoc.12.75" target="_blank" >http://dx.doi.org/10.3762/bjoc.12.75</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.3762/bjoc.12.75" target="_blank" >10.3762/bjoc.12.75</a>
Alternative languages
Result language
angličtina
Original language name
Synthesis and in Vitro Cytotoxicity of Acetylated 3-Fluoro,4-Fluoro and 3,4-Difluoro Analogs of D-glucosamine and D-galactosamine.
Original language description
This work deals with the synthesis of acetylated 3-deoxy-3-fluoro, 4-deoxy-4-fluoro and 3,4-dideoxy-3,4-difluoro analogs of D-glucosamine and D-galactosamine via 1,6-anhydrohexopyranose chemistry. Moreover, the cytotoxicity of the target compounds in selected cancer cells is determined. Introduction of fluorine at C-3 was achieved by the reaction of 1,6-anhydro-2- azido-2-deoxy-4-O-benzyl-β-D-glucopyranose or its 4-fluoro analog with DAST. The retention of configuration in this reaction is discussed. Fluorine at C-4 was installed by the reaction of 1,6:2,3-dianhydro-β-D-talopyranose with DAST, or by fluoridolysis of 1,6:3,4-dianhydro-2-azido-β-D-galactopyranose with KHF2. The amino group was masked as an azide in the synthesis. The 1-O-deacetylated 3-fluoro and 4-fluoro analogs of acetylated D-galactosamine inhibited proliferation of the human prostate cancer cell line PC-3 more than cisplatin and 5-fluorouracil (IC50 28 3 μM and 54 5 μM, respectively).
Czech name
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Czech description
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Classification
Type
J<sub>x</sub> - Unclassified - Peer-reviewed scientific article (Jimp, Jsc and Jost)
CEP classification
CF - Physical chemistry and theoretical chemistry
OECD FORD branch
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Result continuities
Project
Result was created during the realization of more than one project. More information in the Projects tab.
Continuities
I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace
Others
Publication year
2016
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Beilstein Journal of Organic Chemistry
ISSN
1860-5397
e-ISSN
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Volume of the periodical
12
Issue of the periodical within the volume
Apr 20
Country of publishing house
DE - GERMANY
Number of pages
10
Pages from-to
750-759
UT code for WoS article
000374468400001
EID of the result in the Scopus database
2-s2.0-84976389300