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Synthesis of novel test compounds for antiviral chemotherapy of severe acute respiratory syndrome (SARS)

Identifieur interne : 000414 ( PascalFrancis/Curation ); précédent : 000413; suivant : 000415

Synthesis of novel test compounds for antiviral chemotherapy of severe acute respiratory syndrome (SARS)

Auteurs : Andreas J. Kesel [Allemagne]

Source :

RBID : Pascal:05-0492308

Descripteurs français

English descriptors

Abstract

This contribution reviews the synthesis of a range of experimental drugs designed for and aiming at antiviral chemotherapy of severe acute respiratory syndrome (SARS) coronavirus (SARS-CoV)-induced human disease conditions. The selection of 25 test materials includes eleven trioxa-adamantane-triols (TATs) [BN, IBNCA, ABNCA, VANBA, ethylVANBA, euBN, euVANBA, ansaBN, Ehrlich BN, [6]prismaneBN, nitrodiBN], trivially termed bananins, one trioxa-adamantan-ol (TAO) THYMOBA, one bis-bananin pi-bananin (piBN), one triazaadamantane delta-bananin (deltaBN), seven potential nucleic acid-binding drugs (XBQC, INDO, PivINDO, AZTRION, AZADO, AZOCYS, AZOGALL), one potential antiviral interferon-inducer and distant nucleoside analog diazon, one potential HIV protein Vif antagonist AZODIAZON, one folic acid-diazon condensate DIAZONOFOL, and one special nucleoside analog (fructoinosine/fructovir). Four of the eleven bananins (BN, IBNCA, VANBA, euBN) were already demonstrated to constitute effective inhibitors of SARS-CoV NSP10/nsp13 RNA/DNA helicase/NTPase protein ATPase enzymatic function. Bananin (BN) was an effective inhibitor of both SARS-CoV RNA/DNA helicase nucleic acid unwinding function and SARS-CoV (Coronaviridae, Coronavirus) RNA-viral replication in cell culture. In , at least one selected compound of the synthesized test materials represents an interesting drug candidate for treatment of SARS-CoV-induced human disease (SARS). Viewed in aspects of organic chemistry [6]prismaneBN and nitrodiBN are the first true hexaprismane derivatives synthesized, and all reported compounds are entirely new.
pA  
A01 01  1    @0 0929-8673
A03   1    @0 Curr. med. chem.
A05       @2 12
A06       @2 18
A08 01  1  ENG  @1 Synthesis of novel test compounds for antiviral chemotherapy of severe acute respiratory syndrome (SARS)
A11 01  1    @1 KESEL (Andreas J.)
A14 01      @2 Chammiinsterstr. 47, 81827 München @3 DEU @Z 1 aut.
A20       @1 2095-2162
A21       @1 2005
A23 01      @0 ENG
A43 01      @1 INIST @2 22999 @5 354000132425740040
A44       @0 0000 @1 © 2005 INIST-CNRS. All rights reserved.
A45       @0 344 ref.
A47 01  1    @0 05-0492308
A60       @1 P
A61       @0 A
A64 01  1    @0 Current medicinal chemistry
A66 01      @0 NLD
C01 01    ENG  @0 This contribution reviews the synthesis of a range of experimental drugs designed for and aiming at antiviral chemotherapy of severe acute respiratory syndrome (SARS) coronavirus (SARS-CoV)-induced human disease conditions. The selection of 25 test materials includes eleven trioxa-adamantane-triols (TATs) [BN, IBNCA, ABNCA, VANBA, ethylVANBA, euBN, euVANBA, ansaBN, Ehrlich BN, [6]prismaneBN, nitrodiBN], trivially termed bananins, one trioxa-adamantan-ol (TAO) THYMOBA, one bis-bananin pi-bananin (piBN), one triazaadamantane delta-bananin (deltaBN), seven potential nucleic acid-binding drugs (XBQC, INDO, PivINDO, AZTRION, AZADO, AZOCYS, AZOGALL), one potential antiviral interferon-inducer and distant nucleoside analog diazon, one potential HIV protein Vif antagonist AZODIAZON, one folic acid-diazon condensate DIAZONOFOL, and one special nucleoside analog (fructoinosine/fructovir). Four of the eleven bananins (BN, IBNCA, VANBA, euBN) were already demonstrated to constitute effective inhibitors of SARS-CoV NSP10/nsp13 RNA/DNA helicase/NTPase protein ATPase enzymatic function. Bananin (BN) was an effective inhibitor of both SARS-CoV RNA/DNA helicase nucleic acid unwinding function and SARS-CoV (Coronaviridae, Coronavirus) RNA-viral replication in cell culture. In , at least one selected compound of the synthesized test materials represents an interesting drug candidate for treatment of SARS-CoV-induced human disease (SARS). Viewed in aspects of organic chemistry [6]prismaneBN and nitrodiBN are the first true hexaprismane derivatives synthesized, and all reported compounds are entirely new.
C02 01  X    @0 002B02S05
C03 01  X  FRE  @0 Synthèse chimique @5 01
C03 01  X  ENG  @0 Chemical synthesis @5 01
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
C03 02  X  SPA  @0 Antiviral @5 02
C03 03  X  FRE  @0 Chimiothérapie @5 03
C03 03  X  ENG  @0 Chemotherapy @5 03
C03 03  X  SPA  @0 Quimioterapia @5 03
C03 04  X  FRE  @0 Syndrome respiratoire aigu sévère @2 NM @5 04
C03 04  X  ENG  @0 Severe acute respiratory syndrome @2 NM @5 04
C03 04  X  SPA  @0 Síndrome respiratorio agudo severo @2 NM @5 04
C03 05  X  FRE  @0 Article synthèse @5 05
C03 05  X  ENG  @0 Review @5 05
C03 05  X  SPA  @0 Artículo síntesis @5 05
C03 06  X  FRE  @0 Relation structure activité @5 06
C03 06  X  ENG  @0 Structure activity relation @5 06
C03 06  X  SPA  @0 Relación estructura actividad @5 06
C03 07  X  FRE  @0 Gravimétrie @5 07
C03 07  X  ENG  @0 Gravimetric analysis @5 07
C03 07  X  SPA  @0 Gravimetría @5 07
C03 08  X  FRE  @0 Spectrométrie UV @5 08
C03 08  X  ENG  @0 Ultraviolet spectrometry @5 08
C03 08  X  SPA  @0 Espectrometría UV @5 08
C03 09  X  FRE  @0 Spectrométrie IR @5 09
C03 09  X  ENG  @0 Infrared spectrometry @5 09
C03 09  X  SPA  @0 Espectrometría IR @5 09
C03 10  X  FRE  @0 Spectrométrie RMN @5 10
C03 10  X  ENG  @0 NMR spectrometry @5 10
C03 10  X  SPA  @0 Espectrometría RMN @5 10
C03 11  X  FRE  @0 Corrélation hétéronucléaire @5 11
C03 11  X  ENG  @0 Heteronuclear correlation @5 11
C03 11  X  SPA  @0 Correlación heteronuclear @5 11
C03 12  X  FRE  @0 Composé cage @5 12
C03 12  X  ENG  @0 Cage compound @5 12
C03 12  X  SPA  @0 Compuesto jaula @5 12
C03 13  X  FRE  @0 Orthoester @5 13
C03 13  X  ENG  @0 Orthoester @5 13
C03 13  X  SPA  @0 Ortoester @5 13
C03 14  X  FRE  @0 Hétérocycle azote @5 14
C03 14  X  ENG  @0 Nitrogen heterocycle @5 14
C03 14  X  SPA  @0 Heterociclo nitrógeno @5 14
C03 15  X  FRE  @0 Protéomique @5 15
C03 15  X  ENG  @0 Proteomics @5 15
C03 15  X  SPA  @0 Proteómica @5 15
C03 16  X  FRE  @0 Réplication @5 16
C03 16  X  ENG  @0 Replication @5 16
C03 16  X  SPA  @0 Replicación @5 16
C03 17  X  FRE  @0 Virus syndrome respiratoire aigu sévère @2 NW @5 17
C03 17  X  ENG  @0 Severe acute respiratory syndrome virus @2 NW @5 17
C03 17  X  SPA  @0 Severe acute respiratory syndrome virus @2 NW @5 17
C03 18  X  FRE  @0 Bananine @2 NK @4 INC @5 76
C03 19  X  FRE  @0 2,8,9-Trioxaadamantane-3,5,7-triol dérivé @2 NK @4 INC @5 77
C03 20  X  FRE  @0 Prismane dérivé @2 NK @4 INC @5 78
C03 21  X  FRE  @0 Indolo[2,3-b]quinoxaline dérivé @2 NK @4 INC @5 79
C07 01  X  FRE  @0 Virose
C07 01  X  ENG  @0 Viral disease
C07 01  X  SPA  @0 Virosis
C07 02  X  FRE  @0 Infection
C07 02  X  ENG  @0 Infection
C07 02  X  SPA  @0 Infección
C07 03  X  FRE  @0 Coronavirus @2 NW
C07 03  X  ENG  @0 Coronavirus @2 NW
C07 03  X  SPA  @0 Coronavirus @2 NW
C07 04  X  FRE  @0 Coronaviridae @2 NW
C07 04  X  ENG  @0 Coronaviridae @2 NW
C07 04  X  SPA  @0 Coronaviridae @2 NW
C07 05  X  FRE  @0 Nidovirales @2 NW
C07 05  X  ENG  @0 Nidovirales @2 NW
C07 05  X  SPA  @0 Nidovirales @2 NW
C07 06  X  FRE  @0 Virus @2 NW
C07 06  X  ENG  @0 Virus @2 NW
C07 06  X  SPA  @0 Virus @2 NW
C07 07  X  FRE  @0 Appareil respiratoire pathologie @5 53
C07 07  X  ENG  @0 Respiratory disease @5 53
C07 07  X  SPA  @0 Aparato respiratorio patología @5 53
N21       @1 346

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Pascal:05-0492308

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<s5>09</s5>
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<s5>09</s5>
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<s5>10</s5>
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<s5>10</s5>
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<s5>10</s5>
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<s5>11</s5>
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<s5>11</s5>
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<s5>11</s5>
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<s5>12</s5>
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<s5>12</s5>
</fC03>
<fC03 i1="12" i2="X" l="SPA">
<s0>Compuesto jaula</s0>
<s5>12</s5>
</fC03>
<fC03 i1="13" i2="X" l="FRE">
<s0>Orthoester</s0>
<s5>13</s5>
</fC03>
<fC03 i1="13" i2="X" l="ENG">
<s0>Orthoester</s0>
<s5>13</s5>
</fC03>
<fC03 i1="13" i2="X" l="SPA">
<s0>Ortoester</s0>
<s5>13</s5>
</fC03>
<fC03 i1="14" i2="X" l="FRE">
<s0>Hétérocycle azote</s0>
<s5>14</s5>
</fC03>
<fC03 i1="14" i2="X" l="ENG">
<s0>Nitrogen heterocycle</s0>
<s5>14</s5>
</fC03>
<fC03 i1="14" i2="X" l="SPA">
<s0>Heterociclo nitrógeno</s0>
<s5>14</s5>
</fC03>
<fC03 i1="15" i2="X" l="FRE">
<s0>Protéomique</s0>
<s5>15</s5>
</fC03>
<fC03 i1="15" i2="X" l="ENG">
<s0>Proteomics</s0>
<s5>15</s5>
</fC03>
<fC03 i1="15" i2="X" l="SPA">
<s0>Proteómica</s0>
<s5>15</s5>
</fC03>
<fC03 i1="16" i2="X" l="FRE">
<s0>Réplication</s0>
<s5>16</s5>
</fC03>
<fC03 i1="16" i2="X" l="ENG">
<s0>Replication</s0>
<s5>16</s5>
</fC03>
<fC03 i1="16" i2="X" l="SPA">
<s0>Replicación</s0>
<s5>16</s5>
</fC03>
<fC03 i1="17" i2="X" l="FRE">
<s0>Virus syndrome respiratoire aigu sévère</s0>
<s2>NW</s2>
<s5>17</s5>
</fC03>
<fC03 i1="17" i2="X" l="ENG">
<s0>Severe acute respiratory syndrome virus</s0>
<s2>NW</s2>
<s5>17</s5>
</fC03>
<fC03 i1="17" i2="X" l="SPA">
<s0>Severe acute respiratory syndrome virus</s0>
<s2>NW</s2>
<s5>17</s5>
</fC03>
<fC03 i1="18" i2="X" l="FRE">
<s0>Bananine</s0>
<s2>NK</s2>
<s4>INC</s4>
<s5>76</s5>
</fC03>
<fC03 i1="19" i2="X" l="FRE">
<s0>2,8,9-Trioxaadamantane-3,5,7-triol dérivé</s0>
<s2>NK</s2>
<s4>INC</s4>
<s5>77</s5>
</fC03>
<fC03 i1="20" i2="X" l="FRE">
<s0>Prismane dérivé</s0>
<s2>NK</s2>
<s4>INC</s4>
<s5>78</s5>
</fC03>
<fC03 i1="21" i2="X" l="FRE">
<s0>Indolo[2,3-b]quinoxaline dérivé</s0>
<s2>NK</s2>
<s4>INC</s4>
<s5>79</s5>
</fC03>
<fC07 i1="01" i2="X" l="FRE">
<s0>Virose</s0>
</fC07>
<fC07 i1="01" i2="X" l="ENG">
<s0>Viral disease</s0>
</fC07>
<fC07 i1="01" i2="X" l="SPA">
<s0>Virosis</s0>
</fC07>
<fC07 i1="02" i2="X" l="FRE">
<s0>Infection</s0>
</fC07>
<fC07 i1="02" i2="X" l="ENG">
<s0>Infection</s0>
</fC07>
<fC07 i1="02" i2="X" l="SPA">
<s0>Infección</s0>
</fC07>
<fC07 i1="03" i2="X" l="FRE">
<s0>Coronavirus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="03" i2="X" l="ENG">
<s0>Coronavirus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="03" i2="X" l="SPA">
<s0>Coronavirus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="04" i2="X" l="FRE">
<s0>Coronaviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="04" i2="X" l="ENG">
<s0>Coronaviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="04" i2="X" l="SPA">
<s0>Coronaviridae</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="05" i2="X" l="FRE">
<s0>Nidovirales</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="05" i2="X" l="ENG">
<s0>Nidovirales</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="05" i2="X" l="SPA">
<s0>Nidovirales</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="06" i2="X" l="FRE">
<s0>Virus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="06" i2="X" l="ENG">
<s0>Virus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="06" i2="X" l="SPA">
<s0>Virus</s0>
<s2>NW</s2>
</fC07>
<fC07 i1="07" i2="X" l="FRE">
<s0>Appareil respiratoire pathologie</s0>
<s5>53</s5>
</fC07>
<fC07 i1="07" i2="X" l="ENG">
<s0>Respiratory disease</s0>
<s5>53</s5>
</fC07>
<fC07 i1="07" i2="X" l="SPA">
<s0>Aparato respiratorio patología</s0>
<s5>53</s5>
</fC07>
<fN21>
<s1>346</s1>
</fN21>
</pA>
</standard>
</inist>
</record>

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