Unsaturated fluoro-ketopyranosyl nucleosides: Synthesis and biological evaluation of 3-fluoro-4-keto-β- d-glucopyranosyl derivatives of N 4-benzoyl cytosine and N 6-benzoyl adenine
The protected β-nucleosides 1-(2,4,6-tri- O-acetyl-3-deoxy-3-fluoro-β- d-glucopyranosyl)- N 4-benzoyl cytosine ( 2a) and 9-(2,4,6-tri- O-acetyl-3-deoxy-3-fluoro-β- d-glucopyranosyl)- N 6-benzoyl adenine ( 2b), were synthesized by the coupling of peracetylated 3-deoxy-3-fluoro- d-glucopyranose ( 1) w...
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| Published in: | European journal of medicinal chemistry Vol. 43; no. 2; pp. 420 - 428 |
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| Main Authors: | , , , , |
| Format: | Journal Article |
| Language: | English |
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Elsevier Masson SAS
01-02-2008
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| Abstract | The protected β-nucleosides 1-(2,4,6-tri-
O-acetyl-3-deoxy-3-fluoro-β-
d-glucopyranosyl)-
N
4-benzoyl cytosine (
2a) and 9-(2,4,6-tri-
O-acetyl-3-deoxy-3-fluoro-β-
d-glucopyranosyl)-
N
6-benzoyl adenine (
2b), were synthesized by the coupling of peracetylated 3-deoxy-3-fluoro-
d-glucopyranose (
1) with silylated
N
4-benzoyl cytosine and
N
6-benzoyl adenine, respectively. The nucleosides were deacetylated and several subsequent protection and deprotection steps afforded the partially acetylated nucleosides of cytosine
7a and adenine
7b, respectively. Finally, direct oxidation of the free hydroxyl group at 4′-position of
7a and
7b, and simultaneous elimination reaction of the β-acetoxyl group, afforded the desired unsaturated 3-fluoro-4-keto-β-
d-glucopyranosyl derivatives. These newly synthesized compounds were evaluated for their potential antitumor and antiviral activities. Compared to 5FU, the newly synthesized derivatives showed to be more efficient as antitumor growth inhibitors and they exhibited direct antiviral effect toward rotavirus.
We report the synthesis of three novel unsaturated fluoro-ketopyranosyl nucleosides (compounds
8a,
8b and
9a). Compared to 5FU, the newly synthesized derivates showed to be more efficient as antitumor growth inhibitors and they exhibited direct antiviral effect toward rotavirus.
[Display omitted] |
|---|---|
| AbstractList | The protected β-nucleosides 1-(2,4,6-tri-
O-acetyl-3-deoxy-3-fluoro-β-
d-glucopyranosyl)-
N
4-benzoyl cytosine (
2a) and 9-(2,4,6-tri-
O-acetyl-3-deoxy-3-fluoro-β-
d-glucopyranosyl)-
N
6-benzoyl adenine (
2b), were synthesized by the coupling of peracetylated 3-deoxy-3-fluoro-
d-glucopyranose (
1) with silylated
N
4-benzoyl cytosine and
N
6-benzoyl adenine, respectively. The nucleosides were deacetylated and several subsequent protection and deprotection steps afforded the partially acetylated nucleosides of cytosine
7a and adenine
7b, respectively. Finally, direct oxidation of the free hydroxyl group at 4′-position of
7a and
7b, and simultaneous elimination reaction of the β-acetoxyl group, afforded the desired unsaturated 3-fluoro-4-keto-β-
d-glucopyranosyl derivatives. These newly synthesized compounds were evaluated for their potential antitumor and antiviral activities. Compared to 5FU, the newly synthesized derivatives showed to be more efficient as antitumor growth inhibitors and they exhibited direct antiviral effect toward rotavirus.
We report the synthesis of three novel unsaturated fluoro-ketopyranosyl nucleosides (compounds
8a,
8b and
9a). Compared to 5FU, the newly synthesized derivates showed to be more efficient as antitumor growth inhibitors and they exhibited direct antiviral effect toward rotavirus.
[Display omitted] |
| Author | Komiotis, Dimitri Botić, Tanja Manta, Stella Cencič, Avrelija Agelis, George |
| Author_xml | – sequence: 1 givenname: Stella surname: Manta fullname: Manta, Stella organization: Department of Biochemistry and Biotechnology, Laboratory of Organic Chemistry, University of Thessaly, 26 Ploutonos Street, 41221 Larissa, Greece – sequence: 2 givenname: George surname: Agelis fullname: Agelis, George organization: Department of Biochemistry and Biotechnology, Laboratory of Organic Chemistry, University of Thessaly, 26 Ploutonos Street, 41221 Larissa, Greece – sequence: 3 givenname: Tanja surname: Botić fullname: Botić, Tanja organization: Department of Microbiology, Biochemistry and Biotechnology, Faculty of Agriculture, University of Maribor, Vrbanska c.30, 2000 Maribor, Slovenia – sequence: 4 givenname: Avrelija surname: Cencič fullname: Cencič, Avrelija organization: Department of Microbiology, Biochemistry and Biotechnology, Faculty of Agriculture, University of Maribor, Vrbanska c.30, 2000 Maribor, Slovenia – sequence: 5 givenname: Dimitri surname: Komiotis fullname: Komiotis, Dimitri email: dkom@bio.uth.gr organization: Department of Biochemistry and Biotechnology, Laboratory of Organic Chemistry, University of Thessaly, 26 Ploutonos Street, 41221 Larissa, Greece |
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| ContentType | Journal Article |
| Copyright | 2007 Elsevier Masson SAS |
| Copyright_xml | – notice: 2007 Elsevier Masson SAS |
| DOI | 10.1016/j.ejmech.2007.04.001 |
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| Discipline | Chemistry Pharmacy, Therapeutics, & Pharmacology |
| EISSN | 1768-3254 |
| EndPage | 428 |
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| Issue | 2 |
| Keywords | Antiviral Antitumor activity β-Elimination reaction Unsaturated fluoro ketonucleosides |
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| PublicationTitle | European journal of medicinal chemistry |
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| Snippet | The protected β-nucleosides 1-(2,4,6-tri-
O-acetyl-3-deoxy-3-fluoro-β-
d-glucopyranosyl)-
N
4-benzoyl cytosine (
2a) and 9-(2,4,6-tri-... |
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| SubjectTerms | Antitumor activity Antiviral Unsaturated fluoro ketonucleosides β-Elimination reaction |
| Title | Unsaturated fluoro-ketopyranosyl nucleosides: Synthesis and biological evaluation of 3-fluoro-4-keto-β- d-glucopyranosyl derivatives of N 4-benzoyl cytosine and N 6-benzoyl adenine |
| URI | https://dx.doi.org/10.1016/j.ejmech.2007.04.001 |
| Volume | 43 |
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