Design, synthesis, antiviral activity, and SARs of 13a-substituted phenanthroindolizidine alkaloid derivatives.
Identifieur interne : 000F97 ( PubMed/Corpus ); précédent : 000F96; suivant : 000F98Design, synthesis, antiviral activity, and SARs of 13a-substituted phenanthroindolizidine alkaloid derivatives.
Auteurs : Bo Su ; Chunlong Cai ; Meng Deng ; Demin Liang ; Lizhong Wang ; Qingmin WangSource :
- Bioorganic & medicinal chemistry letters [ 1464-3405 ] ; 2014.
English descriptors
- KwdEn :
- Alkaloids (chemical synthesis), Alkaloids (chemistry), Alkaloids (pharmacology), Antiviral Agents (chemical synthesis), Antiviral Agents (chemistry), Antiviral Agents (pharmacology), Dose-Response Relationship, Drug, Drug Design, Indolizines (chemical synthesis), Indolizines (chemistry), Indolizines (pharmacology), Microbial Sensitivity Tests, Phenanthrolines (chemical synthesis), Phenanthrolines (chemistry), Phenanthrolines (pharmacology), RNA, Viral (drug effects), Structure-Activity Relationship, Tobacco Mosaic Virus (drug effects).
- MESH :
- chemical , chemical synthesis : Alkaloids, Antiviral Agents, Indolizines, Phenanthrolines.
- chemical , chemistry : Alkaloids, Antiviral Agents, Indolizines, Phenanthrolines.
- chemical , drug effects : RNA, Viral.
- chemical , pharmacology : Alkaloids, Antiviral Agents, Indolizines, Phenanthrolines.
- drug effects : Tobacco Mosaic Virus.
- Dose-Response Relationship, Drug, Drug Design, Microbial Sensitivity Tests, Structure-Activity Relationship.
Abstract
On the basis of our previous structure-activity relationship (SAR) and antiviral mechanism studies, a series of 13a-substituted phenanthroindolizidine alkaloid analogues (3a-16a, 3b, 4b, 6b, 7b, 10b, and 14b) were designed targeting tobacco mosaic virus (TMV) RNA, synthesized, and evaluated for their antiviral activity against TMV for the first time. The bioassay results showed that most of the synthesized compounds (such as 4a, 6a, 7a, 11a, 14a, 6b, and 14b) exhibited good to excellent antiviral activity against TMV both in vitro and in vivo. Especially, for inactivation effect and curative effect, compounds 4a, 6a, 7a, 11a, 14a, and 14b showed higher activity at both concentrations (500 μg mL(-1) and 100 μg mL(-1)) than commercial Ningnanmycin. Preliminary SARs showed that the substituted groups with hydrogen donor at 13a position were found to be favorable for keeping high antiviral activity. The present work demonstrates that 13a-substituted phenanthroindolizidines can be used as possible lead compounds for developing anti-TMV agents.
DOI: 10.1016/j.bmcl.2014.04.101
PubMed: 24835986
Links to Exploration step
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<front><div type="abstract" xml:lang="en">On the basis of our previous structure-activity relationship (SAR) and antiviral mechanism studies, a series of 13a-substituted phenanthroindolizidine alkaloid analogues (3a-16a, 3b, 4b, 6b, 7b, 10b, and 14b) were designed targeting tobacco mosaic virus (TMV) RNA, synthesized, and evaluated for their antiviral activity against TMV for the first time. The bioassay results showed that most of the synthesized compounds (such as 4a, 6a, 7a, 11a, 14a, 6b, and 14b) exhibited good to excellent antiviral activity against TMV both in vitro and in vivo. Especially, for inactivation effect and curative effect, compounds 4a, 6a, 7a, 11a, 14a, and 14b showed higher activity at both concentrations (500 μg mL(-1) and 100 μg mL(-1)) than commercial Ningnanmycin. Preliminary SARs showed that the substituted groups with hydrogen donor at 13a position were found to be favorable for keeping high antiviral activity. The present work demonstrates that 13a-substituted phenanthroindolizidines can be used as possible lead compounds for developing anti-TMV agents.</div>
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