Synthesis of novel test compounds for antiviral chemotherapy of severe acute respiratory syndrome (SARS)
Identifieur interne : 000414 ( PascalFrancis/Curation ); précédent : 000413; suivant : 000415Synthesis of novel test compounds for antiviral chemotherapy of severe acute respiratory syndrome (SARS)
Auteurs : Andreas J. Kesel [Allemagne]Source :
- Current medicinal chemistry [ 0929-8673 ] ; 2005.
Descripteurs français
- Pascal (Inist)
- Synthèse chimique, Antiviral, Chimiothérapie, Syndrome respiratoire aigu sévère, Article synthèse, Relation structure activité, Gravimétrie, Spectrométrie UV, Spectrométrie IR, Spectrométrie RMN, Corrélation hétéronucléaire, Composé cage, Orthoester, Hétérocycle azote, Protéomique, Réplication, Virus syndrome respiratoire aigu sévère, Bananine, 2,8,9-Trioxaadamantane-3,5,7-triol dérivé, Prismane dérivé, Indolo[2,3-b]quinoxaline dérivé.
English descriptors
- KwdEn :
- Antiviral, Cage compound, Chemical synthesis, Chemotherapy, Gravimetric analysis, Heteronuclear correlation, Infrared spectrometry, NMR spectrometry, Nitrogen heterocycle, Orthoester, Proteomics, Replication, Review, Severe acute respiratory syndrome, Severe acute respiratory syndrome virus, Structure activity relation, Ultraviolet spectrometry.
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.
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<author><name sortKey="Kesel, Andreas J" sort="Kesel, Andreas J" uniqKey="Kesel A" first="Andreas J." last="Kesel">Andreas J. Kesel</name>
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<country>Allemagne</country>
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<term>Gravimetric analysis</term>
<term>Heteronuclear correlation</term>
<term>Infrared spectrometry</term>
<term>NMR spectrometry</term>
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<term>Antiviral</term>
<term>Chimiothérapie</term>
<term>Syndrome respiratoire aigu sévère</term>
<term>Article synthèse</term>
<term>Relation structure activité</term>
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<term>Virus syndrome respiratoire aigu sévère</term>
<term>Bananine</term>
<term>2,8,9-Trioxaadamantane-3,5,7-triol dérivé</term>
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<front><div type="abstract" xml:lang="en">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.</div>
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<s5>01</s5>
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<s5>01</s5>
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<s5>02</s5>
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<s5>02</s5>
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<s5>02</s5>
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<s5>03</s5>
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<s5>03</s5>
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<fC03 i1="03" i2="X" l="SPA"><s0>Quimioterapia</s0>
<s5>03</s5>
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<s2>NM</s2>
<s5>04</s5>
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<fC03 i1="04" i2="X" l="ENG"><s0>Severe acute respiratory syndrome</s0>
<s2>NM</s2>
<s5>04</s5>
</fC03>
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<s5>04</s5>
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<s5>05</s5>
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<s5>05</s5>
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<s5>05</s5>
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<s5>06</s5>
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<s5>06</s5>
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<s5>08</s5>
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<s5>08</s5>
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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>
</fC03>
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<s5>11</s5>
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<s5>12</s5>
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<s5>12</s5>
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<s5>12</s5>
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<s5>13</s5>
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<s5>13</s5>
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<fC03 i1="13" i2="X" l="SPA"><s0>Ortoester</s0>
<s5>13</s5>
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<s5>14</s5>
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<s5>14</s5>
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<s5>14</s5>
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<s5>15</s5>
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<s5>15</s5>
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<s5>16</s5>
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<s5>16</s5>
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<s5>16</s5>
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<s5>17</s5>
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<s2>NW</s2>
<s5>17</s5>
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<fC03 i1="17" i2="X" l="SPA"><s0>Severe acute respiratory syndrome virus</s0>
<s2>NW</s2>
<s5>17</s5>
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<fC03 i1="18" i2="X" l="FRE"><s0>Bananine</s0>
<s2>NK</s2>
<s4>INC</s4>
<s5>76</s5>
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<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>
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<fC03 i1="20" i2="X" l="FRE"><s0>Prismane dérivé</s0>
<s2>NK</s2>
<s4>INC</s4>
<s5>78</s5>
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<fC03 i1="21" i2="X" l="FRE"><s0>Indolo[2,3-b]quinoxaline dérivé</s0>
<s2>NK</s2>
<s4>INC</s4>
<s5>79</s5>
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<s2>NW</s2>
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<s2>NW</s2>
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<fC07 i1="04" i2="X" l="SPA"><s0>Coronaviridae</s0>
<s2>NW</s2>
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<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>
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<fC07 i1="06" i2="X" l="FRE"><s0>Virus</s0>
<s2>NW</s2>
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<fC07 i1="06" i2="X" l="ENG"><s0>Virus</s0>
<s2>NW</s2>
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<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>
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