SrasV1, PascalFrancis, Curation, bibRecord, 000500

Synthesis of cyclopentenyl carbocyclic nucleosides as potential antiviral agents against orthopoxviruses and SARS

Identifieur interne : 000500 ( PascalFrancis/Curation ); précédent : 000499; suivant : 000501

Synthesis 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.

RBID : Pascal:06-0304976

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 :
- Antiviral, Biological activity, Carbanucleoside, Chemical synthesis, Coronavirus, Cowpox virus, In vitro, Orthopoxvirus, Severe acute respiratory syndrome virus, Venezuelan equine encephalomyelitis virus, West Nile virus, Yellow fever virus.

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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A11	`01`	`1`		`@1 JONG HYUN CHO`
A11	`02`	`1`		`@1 BERNARD (Dale L.)`
A11	`03`	`1`		`@1 SIDWELL (Robert W.)`
A11	`04`	`1`		`@1 KERN (Earl R.)`
A11	`05`	`1`		`@1 CHU (Chung K.)`
A14	`01`			`@1 The University of Georgia College of Pharmacy @2 Athens, Georgia 30602 @3 USA @Z 1 aut. @Z 5 aut.`
A14	`02`			`@1 Institute for Antiviral Research, Utah State University @2 Logan, Utah 84322 @3 USA @Z 2 aut. @Z 3 aut.`
A14	`03`			`@1 University of Alabama School of Medicine @2 Birmingham, Alabama 35294 @3 USA @Z 4 aut.`
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A21				`@1 2006`
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A44				`@0 0000 @1 © 2006 INIST-CNRS. All rights reserved.`
A45				`@0 19 ref.`
A47	`01`	`1`		`@0 06-0304976`
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A64	`01`	`1`		`@0 Journal of medicinal chemistry : (Print)`
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C01	`01`		`ENG`	@0 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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C03	`01`	`X`	`SPA`	`@0 Síntesis química @5 01`
C03	`02`	`X`	`FRE`	`@0 Antiviral @5 02`
C03	`02`	`X`	`ENG`	`@0 Antiviral @5 02`
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C03	`05`	`X`	`FRE`	`@0 Virus fièvre jaune @2 NW @5 05`
C03	`05`	`X`	`ENG`	`@0 Yellow fever virus @2 NW @5 05`
C03	`05`	`X`	`SPA`	`@0 Yellow fever virus @2 NW @5 05`
C03	`06`	`X`	`FRE`	`@0 Virus West Nile @2 NW @5 06`
C03	`06`	`X`	`ENG`	`@0 West Nile virus @2 NW @5 06`
C03	`06`	`X`	`SPA`	`@0 West Nile virus @2 NW @5 06`
C03	`07`	`X`	`FRE`	`@0 Virus encéphalite équine Venezuela @2 NW @5 07`
C03	`07`	`X`	`ENG`	`@0 Venezuelan equine encephalomyelitis virus @2 NW @5 07`
C03	`07`	`X`	`SPA`	`@0 Venezuelan equine encephalomyelitis virus @2 NW @5 07`
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C03	`08`	`X`	`ENG`	`@0 Coronavirus @2 NW @5 08`
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C03	`09`	`X`	`FRE`	`@0 Virus syndrome respiratoire aigu sévère @2 NW @5 09`
C03	`09`	`X`	`ENG`	`@0 Severe acute respiratory syndrome virus @2 NW @5 09`
C03	`09`	`X`	`SPA`	`@0 Severe acute respiratory syndrome virus @2 NW @5 09`
C03	`10`	`X`	`FRE`	`@0 Activité biologique @5 10`
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C03	`10`	`X`	`SPA`	`@0 Actividad biológica @5 10`
C03	`11`	`X`	`FRE`	`@0 In vitro @5 11`
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C03	`13`	`X`	`FRE`	`@0 Cyclopentène dérivé @2 NK @4 INC @5 77`
C03	`14`	`X`	`FRE`	`@0 Carbanucléoside @4 CD @5 96`
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C07	`01`	`X`	`FRE`	`@0 Chordopoxvirinae @2 NW`
C07	`01`	`X`	`ENG`	`@0 Chordopoxvirinae @2 NW`
C07	`01`	`X`	`SPA`	`@0 Chordopoxvirinae @2 NW`
C07	`02`	`X`	`FRE`	`@0 Poxviridae @2 NW`
C07	`02`	`X`	`ENG`	`@0 Poxviridae @2 NW`
C07	`02`	`X`	`SPA`	`@0 Poxviridae @2 NW`
C07	`03`	`X`	`FRE`	`@0 Virus @2 NW`
C07	`03`	`X`	`ENG`	`@0 Virus @2 NW`
C07	`03`	`X`	`SPA`	`@0 Virus @2 NW`
C07	`04`	`X`	`FRE`	`@0 Virus groupe fièvre jaune @2 NW`
C07	`04`	`X`	`ENG`	`@0 Yellow fever group virus @2 NW`
C07	`04`	`X`	`SPA`	`@0 Yellow fever group virus @2 NW`
C07	`05`	`X`	`FRE`	`@0 Flavivirus @2 NW`
C07	`05`	`X`	`ENG`	`@0 Flavivirus @2 NW`
C07	`05`	`X`	`SPA`	`@0 Flavivirus @2 NW`
C07	`06`	`X`	`FRE`	`@0 Flaviviridae @2 NW`
C07	`06`	`X`	`ENG`	`@0 Flaviviridae @2 NW`
C07	`06`	`X`	`SPA`	`@0 Flaviviridae @2 NW`
C07	`07`	`X`	`FRE`	`@0 Virus groupe encéphalite japonaise @2 NW`
C07	`07`	`X`	`ENG`	`@0 Japanese encephalitis group virus @2 NW`
C07	`07`	`X`	`SPA`	`@0 Japanese encephalitis group virus @2 NW`
C07	`08`	`X`	`FRE`	`@0 Alphavirus @2 NW`
C07	`08`	`X`	`ENG`	`@0 Alphavirus @2 NW`
C07	`08`	`X`	`SPA`	`@0 Alphavirus @2 NW`
C07	`09`	`X`	`FRE`	`@0 Togaviridae @2 NW`
C07	`09`	`X`	`ENG`	`@0 Togaviridae @2 NW`
C07	`09`	`X`	`SPA`	`@0 Togaviridae @2 NW`
C07	`10`	`X`	`FRE`	`@0 Coronaviridae @2 NW`
C07	`10`	`X`	`ENG`	`@0 Coronaviridae @2 NW`
C07	`10`	`X`	`SPA`	`@0 Coronaviridae @2 NW`
C07	`11`	`X`	`FRE`	`@0 Nidovirales @2 NW`
C07	`11`	`X`	`ENG`	`@0 Nidovirales @2 NW`
C07	`11`	`X`	`SPA`	`@0 Nidovirales @2 NW`
N21				`@1 198`

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Pascal:06-0304976

Le document en format XML

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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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<fA11 i1="01" i2="1"><s1>JONG HYUN CHO</s1>
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<fA14 i1="02"><s1>Institute for Antiviral Research, Utah State University</s1>
<s2>Logan, Utah 84322</s2>
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<sZ>2 aut.</sZ>
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<fA14 i1="03"><s1>University of Alabama School of Medicine</s1>
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<fC01 i1="01" l="ENG"><s0>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.</s0>
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<s5>02</s5>
</fC03>
<fC03 i1="02" i2="X" l="SPA"><s0>Antiviral</s0>
<s5>02</s5>
</fC03>
<fC03 i1="03" i2="X" l="FRE"><s0>Orthopoxvirus</s0>
<s2>NW</s2>
<s5>03</s5>
</fC03>
<fC03 i1="03" i2="X" l="ENG"><s0>Orthopoxvirus</s0>
<s2>NW</s2>
<s5>03</s5>
</fC03>
<fC03 i1="03" i2="X" l="SPA"><s0>Orthopoxvirus</s0>
<s2>NW</s2>
<s5>03</s5>
</fC03>
<fC03 i1="04" i2="X" l="FRE"><s0>Virus variole bovine</s0>
<s2>NW</s2>
<s5>04</s5>
</fC03>
<fC03 i1="04" i2="X" l="ENG"><s0>Cowpox virus</s0>
<s2>NW</s2>
<s5>04</s5>
</fC03>
<fC03 i1="04" i2="X" l="SPA"><s0>Cowpox virus</s0>
<s2>NW</s2>
<s5>04</s5>
</fC03>
<fC03 i1="05" i2="X" l="FRE"><s0>Virus fièvre jaune</s0>
<s2>NW</s2>
<s5>05</s5>
</fC03>
<fC03 i1="05" i2="X" l="ENG"><s0>Yellow fever virus</s0>
<s2>NW</s2>
<s5>05</s5>
</fC03>
<fC03 i1="05" i2="X" l="SPA"><s0>Yellow fever virus</s0>
<s2>NW</s2>
<s5>05</s5>
</fC03>
<fC03 i1="06" i2="X" l="FRE"><s0>Virus West Nile</s0>
<s2>NW</s2>
<s5>06</s5>
</fC03>
<fC03 i1="06" i2="X" l="ENG"><s0>West Nile virus</s0>
<s2>NW</s2>
<s5>06</s5>
</fC03>
<fC03 i1="06" i2="X" l="SPA"><s0>West Nile virus</s0>
<s2>NW</s2>
<s5>06</s5>
</fC03>
<fC03 i1="07" i2="X" l="FRE"><s0>Virus encéphalite équine Venezuela</s0>
<s2>NW</s2>
<s5>07</s5>
</fC03>
<fC03 i1="07" i2="X" l="ENG"><s0>Venezuelan equine encephalomyelitis virus</s0>
<s2>NW</s2>
<s5>07</s5>
</fC03>
<fC03 i1="07" i2="X" l="SPA"><s0>Venezuelan equine encephalomyelitis virus</s0>
<s2>NW</s2>
<s5>07</s5>
</fC03>
<fC03 i1="08" i2="X" l="FRE"><s0>Coronavirus</s0>
<s2>NW</s2>
<s5>08</s5>
</fC03>
<fC03 i1="08" i2="X" l="ENG"><s0>Coronavirus</s0>
<s2>NW</s2>
<s5>08</s5>
</fC03>
<fC03 i1="08" i2="X" l="SPA"><s0>Coronavirus</s0>
<s2>NW</s2>
<s5>08</s5>
</fC03>
<fC03 i1="09" i2="X" l="FRE"><s0>Virus syndrome respiratoire aigu sévère</s0>
<s2>NW</s2>
<s5>09</s5>
</fC03>
<fC03 i1="09" i2="X" l="ENG"><s0>Severe acute respiratory syndrome virus</s0>
<s2>NW</s2>
<s5>09</s5>
</fC03>
<fC03 i1="09" i2="X" l="SPA"><s0>Severe acute respiratory syndrome virus</s0>
<s2>NW</s2>
<s5>09</s5>
</fC03>
<fC03 i1="10" i2="X" l="FRE"><s0>Activité biologique</s0>
<s5>10</s5>
</fC03>
<fC03 i1="10" i2="X" l="ENG"><s0>Biological activity</s0>
<s5>10</s5>
</fC03>
<fC03 i1="10" i2="X" l="SPA"><s0>Actividad biológica</s0>
<s5>10</s5>
</fC03>
<fC03 i1="11" i2="X" l="FRE"><s0>In vitro</s0>
<s5>11</s5>
</fC03>
<fC03 i1="11" i2="X" l="ENG"><s0>In vitro</s0>
<s5>11</s5>
</fC03>
<fC03 i1="11" i2="X" l="SPA"><s0>In vitro</s0>
<s5>11</s5>
</fC03>
<fC03 i1="12" i2="X" l="FRE"><s0>1,2,3-Triazole-4-carboxamide(1-[4,5-dihydroxy-3-hydroxyméthylcyclopent-2-ényl])</s0>
<s2>NK</s2>
<s2>FR</s2>
<s4>INC</s4>
<s5>76</s5>
</fC03>
<fC03 i1="13" i2="X" l="FRE"><s0>Cyclopentène dérivé</s0>
<s2>NK</s2>
<s4>INC</s4>
<s5>77</s5>
</fC03>
<fC03 i1="14" i2="X" l="FRE"><s0>Carbanucléoside</s0>
<s4>CD</s4>
<s5>96</s5>
</fC03>
<fC03 i1="14" i2="X" l="ENG"><s0>Carbanucleoside</s0>
<s4>CD</s4>
<s5>96</s5>
</fC03>
<fC07 i1="01" i2="X" l="FRE"><s0>Chordopoxvirinae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="01" i2="X" l="ENG"><s0>Chordopoxvirinae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="01" i2="X" l="SPA"><s0>Chordopoxvirinae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="02" i2="X" l="FRE"><s0>Poxviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="02" i2="X" l="ENG"><s0>Poxviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="02" i2="X" l="SPA"><s0>Poxviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="03" i2="X" l="FRE"><s0>Virus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="03" i2="X" l="ENG"><s0>Virus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="03" i2="X" l="SPA"><s0>Virus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="04" i2="X" l="FRE"><s0>Virus groupe fièvre jaune</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="04" i2="X" l="ENG"><s0>Yellow fever group virus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="04" i2="X" l="SPA"><s0>Yellow fever group virus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="05" i2="X" l="FRE"><s0>Flavivirus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="05" i2="X" l="ENG"><s0>Flavivirus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="05" i2="X" l="SPA"><s0>Flavivirus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="06" i2="X" l="FRE"><s0>Flaviviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="06" i2="X" l="ENG"><s0>Flaviviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="06" i2="X" l="SPA"><s0>Flaviviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="07" i2="X" l="FRE"><s0>Virus groupe encéphalite japonaise</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="07" i2="X" l="ENG"><s0>Japanese encephalitis group virus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="07" i2="X" l="SPA"><s0>Japanese encephalitis group virus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="08" i2="X" l="FRE"><s0>Alphavirus</s0>
<s2>NW</s2>
</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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   |wiki=    Sante
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   |texte=   Synthesis of cyclopentenyl carbocyclic nucleosides as potential antiviral agents against orthopoxviruses and SARS
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Synthesis of cyclopentenyl carbocyclic nucleosides as potential antiviral agents against orthopoxviruses and SARS

Synthesis of cyclopentenyl carbocyclic nucleosides as potential antiviral agents against orthopoxviruses and SARS

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