Application of "Hydrogen-Bonding Interaction" in Drug Design. Part 2: Design, Synthesis, and Structure-Activity Relationships of Thiophosphoramide Derivatives as Novel Antiviral and Antifungal Agents.
Identifieur interne : 001365 ( Main/Exploration ); précédent : 001364; suivant : 001366Application of "Hydrogen-Bonding Interaction" in Drug Design. Part 2: Design, Synthesis, and Structure-Activity Relationships of Thiophosphoramide Derivatives as Novel Antiviral and Antifungal Agents.
Auteurs : Aidang Lu [République populaire de Chine] ; Yuanyuan Ma [République populaire de Chine] ; Ziwen Wang [République populaire de Chine] ; Zhenghong Zhou [République populaire de Chine] ; Qingmin Wang [République populaire de Chine]Source :
- Journal of agricultural and food chemistry [ 1520-5118 ] ; 2015.
Descripteurs français
- KwdFr :
- MESH :
- pharmacologie : Antifongiques, Antiviraux.
- synthèse chimique : Antifongiques, Antiviraux.
- Antifongiques, Antiviraux, Champignons, Conception de médicament, Liaison hydrogène, Relation structure-activité, Virus de la mosaïque du tabac.
English descriptors
- KwdEn :
- Antifungal Agents (chemical synthesis), Antifungal Agents (chemistry), Antifungal Agents (pharmacology), Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Drug Design, Fungi (drug effects), Hydrogen Bonding, Structure-Activity Relationship, Tobacco Mosaic Virus (drug effects).
- MESH :
- chemical , chemical synthesis : Antifungal Agents, Antiviral Agents.
- chemical , chemistry : Antifungal Agents, Antiviral Agents.
- chemical , pharmacology : Antifungal Agents, Antiviral Agents.
- drug effects : Fungi, Tobacco Mosaic Virus.
- Drug Design, Hydrogen Bonding, Structure-Activity Relationship.
Abstract
On the basis of the structure of natural product harmine, lead compound 18, and the structure of compounds in part 1, a series of thiophosphoramide derivatives 1-17 were designed and synthesized from various amines in one step. Their antiviral and antifungal activities were evaluated. Most of the compounds showed significantly higher antiviral activity against tobacco mosaic virus (TMV) than commercial virucide ribavirin. Compound (R,R)-17 showed the best anti-TMV activity in vitro (70%/500 μg/mL and 33%/100 μg/mL) and in vivo (inactivation effect, 68%/500 μg/mL and 30%/100 μg/mL; curative effect, 64%/500 μg/mL and 31%/100 μg/mL; protection effect, 66%/500 μg/mL and 31%/100 μg/mL), which is higher than that of ningnanmycin and lead compound 18. The antiviral activity of (R,R)-17·HCl is about similar to that of (R,R)-17. However, the antifungal activity of (R,R)-17·HCl against Puccinia sorghi is slightly lower than that of (R,R)-17. The systematic study provides compelling evidence that these simple thiophosphoramide compounds could become efficient antiviral and antifungal agents.
DOI: 10.1021/acs.jafc.5b02676
PubMed: 26485246
Affiliations:
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structure-activité</term><term>Virus de la mosaïque du tabac</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">On the basis of the structure of natural product harmine, lead compound 18, and the structure of compounds in part 1, a series of thiophosphoramide derivatives 1-17 were designed and synthesized from various amines in one step. Their antiviral and antifungal activities were evaluated. Most of the compounds showed significantly higher antiviral activity against tobacco mosaic virus (TMV) than commercial virucide ribavirin. Compound (R,R)-17 showed the best anti-TMV activity in vitro (70%/500 μg/mL and 33%/100 μg/mL) and in vivo (inactivation effect, 68%/500 μg/mL and 30%/100 μg/mL; curative effect, 64%/500 μg/mL and 31%/100 μg/mL; protection effect, 66%/500 μg/mL and 31%/100 μg/mL), which is higher than that of ningnanmycin and lead compound 18. The antiviral activity of (R,R)-17·HCl is about similar to that of (R,R)-17. However, the antifungal activity of (R,R)-17·HCl against Puccinia sorghi is slightly lower than that of (R,R)-17. The systematic study provides compelling evidence that these simple thiophosphoramide compounds could become efficient antiviral and antifungal agents. </div></front></TEI><affiliations><list><country><li>République populaire de Chine</li></country><settlement><li>Tianjin</li></settlement></list><tree><country name="République populaire de Chine"><noRegion><name sortKey="Lu, Aidang" sort="Lu, Aidang" uniqKey="Lu A" first="Aidang" last="Lu">Aidang Lu</name></noRegion><name sortKey="Ma, Yuanyuan" sort="Ma, Yuanyuan" uniqKey="Ma Y" first="Yuanyuan" last="Ma">Yuanyuan Ma</name><name sortKey="Wang, Qingmin" sort="Wang, Qingmin" uniqKey="Wang Q" first="Qingmin" last="Wang">Qingmin Wang</name><name sortKey="Wang, Ziwen" sort="Wang, Ziwen" uniqKey="Wang Z" first="Ziwen" last="Wang">Ziwen Wang</name><name sortKey="Zhou, Zhenghong" sort="Zhou, Zhenghong" uniqKey="Zhou Z" first="Zhenghong" last="Zhou">Zhenghong Zhou</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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