Synthesis of cyclopentenyl carbocyclic nucleosides as potential antiviral agents against orthopoxviruses and SARS
Identifieur interne : 000500 ( PascalFrancis/Curation ); précédent : 000499; suivant : 000501Synthesis of cyclopentenyl carbocyclic nucleosides as potential antiviral agents against orthopoxviruses and SARS
Auteurs : JONG HYUN CHO [États-Unis] ; Dale L. Bernard [États-Unis] ; Robert W. Sidwell [États-Unis] ; Earl R. Kern [États-Unis] ; Chung K. Chu [États-Unis]Source :
- Journal of medicinal chemistry : (Print) [ 0022-2623 ] ; 2006.
Descripteurs français
- Pascal (Inist)
- Synthèse chimique, Antiviral, Orthopoxvirus, Virus variole bovine, Virus fièvre jaune, Virus West Nile, Virus encéphalite équine Venezuela, Coronavirus, Virus syndrome respiratoire aigu sévère, Activité biologique, In vitro, 1,2,3-Triazole-4-carboxamide(1-[4,5-dihydroxy-3-hydroxyméthylcyclopent-2-ényl]), Cyclopentène dérivé, Carbanucléoside.
English descriptors
- KwdEn :
Abstract
A practical and convenient methodology for the synthesis of chiral cyclopentenol derivative (+)-12a has been developed as the key intermediate that was utilized for the synthesis of biologically active carbocyclic nucleosides. The selective protection of allylic hydroxyl group followed by the ring-closing metathesis (RCM) reaction with Grubbs catalysts provided (+)-12a on a 10 g scale with 52% overall yield from D-ribose (4). The key intermediate (+)-12a was utilized for the synthesis of unnatural five-membered ring heterocyclic carbocyclic nucleosides. The newly synthesized 1,2,3-triazole analogue (17c) exhibited potent antiviral activity (EC50 0.4 μM) against vaccinia virus and moderate activities (EC50 39 μM) against cowpox virus and severe acute respiratory syndrome coronavirus (SARSCoV) (EC50 47 μM). The 1,2,4-triazole analogue (17a) also exhibited moderate antiviral activity (EC50 21 μM) against SARSCoV.
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<front><div type="abstract" xml:lang="en">A practical and convenient methodology for the synthesis of chiral cyclopentenol derivative (+)-12a has been developed as the key intermediate that was utilized for the synthesis of biologically active carbocyclic nucleosides. The selective protection of allylic hydroxyl group followed by the ring-closing metathesis (RCM) reaction with Grubbs catalysts provided (+)-12a on a 10 g scale with 52% overall yield from D-ribose (4). The key intermediate (+)-12a was utilized for the synthesis of unnatural five-membered ring heterocyclic carbocyclic nucleosides. The newly synthesized 1,2,3-triazole analogue (17c) exhibited potent antiviral activity (EC<sub>50</sub>
0.4 μM) against vaccinia virus and moderate activities (EC<sub>50</sub>
39 μM) against cowpox virus and severe acute respiratory syndrome coronavirus (SARSCoV) (EC<sub>50</sub>
47 μM). The 1,2,4-triazole analogue (17a) also exhibited moderate antiviral activity (EC<sub>50</sub>
21 μM) against SARSCoV.</div>
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</fC07>
<fC07 i1="08" i2="X" l="ENG"><s0>Alphavirus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="08" i2="X" l="SPA"><s0>Alphavirus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="09" i2="X" l="FRE"><s0>Togaviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="09" i2="X" l="ENG"><s0>Togaviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="09" i2="X" l="SPA"><s0>Togaviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="10" i2="X" l="FRE"><s0>Coronaviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="10" i2="X" l="ENG"><s0>Coronaviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="10" i2="X" l="SPA"><s0>Coronaviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="11" i2="X" l="FRE"><s0>Nidovirales</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="11" i2="X" l="ENG"><s0>Nidovirales</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="11" i2="X" l="SPA"><s0>Nidovirales</s0>
<s2>NW</s2>
</fC07>
<fN21><s1>198</s1>
</fN21>
</pA>
</standard>
</inist>
</record>
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