| Publication Type |
Journal Article |
| Title |
Synthesis and Exploitation of the Biological Profile of Novel Guanidino Xylofuranose Derivatives |
| Authors |
Andreia Fortuna Rita Goncalves-Pereira Paulo J. Costa Radek Jorda Veronika Vojackova Gabriel Gonzalez V Heise Rene Csuk M. Conceição Oliveira Nuno Manuel Xavier |
| Groups |
BioMol HC |
| Journal |
CHEMMEDCHEM |
| Year |
2022 |
| Month |
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|
| Volume |
17 |
| Number |
14 |
| Pages |
|
| Abstract |
The synthesis and biological evaluation of novel guanidino sugars as isonucleoside analogs is described. 5-Guanidino xylofuranoses containing 3-O-saturated/unsaturated hydrocarbon or aromatic-containing moieties were accessed from 5-azido xylofuranoses via reduction followed by guanidinylation with N,N -bis(tert-butoxycarbonyl)-N -triflylguanidine. Molecules comprising novel types of isonucleosidic structures including 5-guanidino 3-O-methyl-branched N-benzyltriazole isonucleosides and a guanidinomethyltriazole 3 -O-dodecyl xylofuranos-5 -yl isonucleoside were accessed. The guanidinomethyltriazole derivative and a 3-O-dodecyl (N-Boc)guanidino xylofuranose were revealed as selective inhibitors of acetylcholinesterase (K-i=22.87 and 7.49 mu M, respectively). The latter also showed moderate antiproliferative effects in chronic myeloid leukemia (K562) and breast cancer (MCF-7) cells. An aminomethyltriazole 5 -isonucleoside was the most potent molecule with low micromolar GI(50) values in both cells (GI(50)=6.33 mu M, 8.45 mu M), similar to that of the drug 5-fluorouracil in MCF-7 cells. Moreover, the most bioactive compounds showed low toxicity in human fibroblasts, further indicating their interest as promising lead molecules. |
| DOI |
http://dx.doi.org/10.1002/cmdc.202200180 |
| ISBN |
|
| Publisher |
WILEY-V C H VERLAG GMBH |
| Book Title |
|
| ISSN |
1860-7179 |
| EISSN |
1860-7187 |
| Conference Name |
|
| Bibtex ID |
WOS:000804905400001 |
| Observations |
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