Design, synthesis, antiviral activity, and SARs of 13a-substituted phenanthroindolizidine alkaloid derivatives

Su, Bo; Cai, Chunlong; Deng, Meng; Liang, Demin; Wang, Lizhong; Wang, Qingmin

doi:10.1016/j.bmcl.2014.04.101

Cited by 38 publications

(18 citation statements)

References 22 publications

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“…1 including (+)-oleracein, 1 b (−)-trolline, 1 c (+)-crispine 1 d and lamellarin alkaloids such as lamellarin D and lamellarin α-20-sulfate. 1 f Most of the pyrrolo[2,1- a ]isoquinoline alkaloids display remarkable antitumor, 2 antibacterial and antiviral, 3 anti-inflammatory, 4 antidepressant 5 and cardiovascular 6 properties. Furthermore, lamellarin D, isolated from marine molluscs, has been reported to be an inhibitor of human topoisomerase, 7 whereas lamellarin α-20-sulfate inhibits the enzyme HIV integrase.…”

Section: Introductionmentioning

confidence: 99%

Highly diastereoselective construction of novel dispiropyrrolo[2,1-a]isoquinoline derivativesviamulticomponent 1,3-dipolar cycloaddition of cyclic diketones-based tetrahydroisoquinoliniumN-ylides

et al. 2019

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Section: Introductionmentioning

confidence: 99%

Highly diastereoselective construction of novel dispiropyrrolo[2,1-a]isoquinoline derivativesviamulticomponent 1,3-dipolar cycloaddition of cyclic diketones-based tetrahydroisoquinoliniumN-ylides

et al. 2019

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“…Antivirus activity results showed that some of the C-13asubstituted derivatives were indeed much more potent than antofine. 30 Therefore, these results demonstrated that further studies based on this line was in demand.…”

Section: ■ Introductionmentioning

confidence: 73%

Spatial Configuration and Three-Dimensional Conformation Directed Design, Synthesis, Antiviral Activity, and Structure–Activity Relationships of Phenanthroindolizidine Analogues

Cai

Deng

et al. 2016

J. Agric. Food Chem.

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Our recent investigation on the antiviral activities against tobacco mosaic virus (TMV) of phenanthroindolizidine alkaloid analogues preliminarily revealed that the basic skeleton and substitution pattern at the C13a position of the molecule, which are closely related to the spatial arrangement of the molecule, have great effects on the biological activity. To further study the in-depth influence of spatial configuration and three-dimensional (3D) conformation of the molecules on their anti-TMV activities and related structure-activity relationship (SAR), a series of D-ring opened derivatives 3, 4, 5a-5j, 6, and 7, chiral 13a- and/or 14-substituted phenanthroindolizidine analogues 10-12 and 18-20, and their enantiomers ent-10-ent-12 and ent-18-ent-20 were synthesized and evaluated for their anti-TMV activities. Bioassay results showed that most of the chiral phenanthroindolizidines displayed good to excellent in vivo anti-TMV activity. Among these compounds, ent-11 showed more potent activity than Ningnanmycin (one of the most successful commercial antiviral agents), thus emerging as a potential inhibitor of the plant virus. Further SARs were also discussed for the first time under the chiral scenario, demonstrating that both spatial configuration and 3D conformation of the molecules are crucial for keeping high anti-TMV activity.

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“…The inactivating, curative and protective activities of compound 54 against TMV were 75.3, 76.2 and 68.4% at 500 mg/L, respectively. The methoxy group on the phenanthrene unit significantly affects the antiviral activity of the compounds ( Su et al, 2014a ). Antiviral activity of other representative tylophorine analogues is shown in Table 2 .…”

Section: Antiviral Active Compoundsmentioning

confidence: 99%

Recent Research Progress: Discovery of Anti-Plant Virus Agents Based on Natural Scaffold

et al. 2022

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Plant virus diseases, also known as “plant cancers”, cause serious harm to the agriculture of the world and huge economic losses every year. Antiviral agents are one of the most effective ways to control plant virus diseases. Ningnanmycin is currently the most successful anti-plant virus agent, but its field control effect is not ideal due to its instability. In recent years, great progress has been made in the research and development of antiviral agents, the mainstream research direction is to obtain antiviral agents or lead compounds based on structural modification of natural products. However, no antiviral agent has been able to completely inhibit plant viruses. Therefore, the development of highly effective antiviral agents still faces enormous challenges. Therefore, we reviewed the recent research progress of anti-plant virus agents based on natural products in the past decade, and discussed their structure-activity relationship (SAR) and mechanism of action. It is hoped that this review can provide new inspiration for the discovery and mechanism of action of novel antiviral agents.

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Design, synthesis, antiviral activity, and SARs of 13a-substituted phenanthroindolizidine alkaloid derivatives

Cited by 38 publications

References 22 publications

Highly diastereoselective construction of novel dispiropyrrolo[2,1-a]isoquinoline derivativesviamulticomponent 1,3-dipolar cycloaddition of cyclic diketones-based tetrahydroisoquinoliniumN-ylides

Highly diastereoselective construction of novel dispiropyrrolo[2,1-a]isoquinoline derivativesviamulticomponent 1,3-dipolar cycloaddition of cyclic diketones-based tetrahydroisoquinoliniumN-ylides

Spatial Configuration and Three-Dimensional Conformation Directed Design, Synthesis, Antiviral Activity, and Structure–Activity Relationships of Phenanthroindolizidine Analogues

Recent Research Progress: Discovery of Anti-Plant Virus Agents Based on Natural Scaffold

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