Arylnaphthalene lignans. Synthesis of justicidin E, taiwanin C, dehydrodimethylconidendrin, and dehydrodimethylretrodendrin

Stevenson, Robert; Holmes, T. L.

doi:10.1021/jo00821a037

Cited by 46 publications

(9 citation statements)

References 2 publications

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“…Several SARs were examined including the effect of epimerization, ring D opening, changes to other ring systems such as cyclic ether, cyclic lactam, cyclic thioether, cyclopentanone, and carbo cyclopentane rings [96,[98][99][100]. Some of retroarylnaphthalene lignans [101,102] present in nature such as justicidin E (59) [103], retrojusticidin B (61), and retrochinensin (58) as well as some aryltetraline lignans like formosolactone (60) [104] and α-conidendrin (59) [105] showed antimicrobial and anti-HIV reverse transcriptase activities [106,107] (Fig. 8).…”

Section: Ring D Modificationsmentioning

confidence: 99%

Podophyllotoxin Derivatives: Current Synthetic Approaches for New Anticancer Agents

You¹

2005

CPD

188

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Podophyllotoxin is an antimitotic natural product. Its inhibitory activity on cell growth led to the development of the clinically valuable anticancer agents, etoposide, teniposide and the water-soluble prodrug, etoposide phosphate. The cytotoxic mechanism of these drugs is the inhibition of topoisomerase II, unlike the lead compound which inhibits mitosis. Through extensive structure-activity relationship studies, several potential drug candidates were synthesized such as GL-331, TOP 53, NK611, and azatoxin. Recently, more complex and diverse analogues have been synthesized either to get more potent compounds or to overcome drug resistance. At the same time, a number of prodrug approaches have been tried to enhance the tumor selectivity or to increase the aqueous solubility. The prodrugs can release cytotoxic etoposide through the actions of hydrolysis, enzymes or catalytic antibodies. More sophisticated prodrug strategies have been applied in etoposide and these produced some interesting results. In this review, the current research trends in the design of new derivatives will be covered with a brief introduction of podophyllotoxin and related analogues.

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Section: Ring D Modificationsmentioning

confidence: 99%

Podophyllotoxin Derivatives: Current Synthetic Approaches for New Anticancer Agents

You¹

2005

CPD

188

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“…Signals ascribable to two methoxyl groups were observed at ô 4.13 and 3.85. The two methoxyls cannot be located on ring C since for the methoxyls is > 0.2 ppm [4]. The downfield methoxyl signal (ô 4.13) is assigned to C-4 position by the close similarity of the chemical shift to the corresponding one of justicidin A (ö 4.08) [51.…”

Section: Resultsmentioning

confidence: 99%

Two New Arylnaphthalide Lignans from Justicia flava Roots*

Olaniyi¹

1982

Planta Med

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“…Since the first synthesis of an arylnaphthalene lignan lactone skeleton in 1895 by the Bucher group (Michael and Bucher 1895) via the condensation of arylpropiolic Pharmacy,Gachon University,191 Hambakmoe-ro, Yeonsu-gu, Incheon 21936, Korea e-mail: dyshin@gachon.ac.kr acids, various synthetic approaches for arylnaphthalene lignan lactones have been designed and applied successfully. Major synthetic approaches include the intramolecular Diels-Alder reaction for the construction of an arylnaphthalene lactone from arylpropiolic anhydride Stevenson 1964, 1965;Maclean and Stevenson 1966;Block and Stevenson 1971;Stevenson 1970, 1971;Stevenson and Holmes 1971;Stevenson and Block 1971;Block and Stevenson 1973;Weber 1989, 1991;Anastas and Stevenson 1991;Park et al 2014). Intermolecular Diels-Alder approaches were also investigated using isobenzofurans and acetylenedicarboxylate (de Silva et al 1980;Plaumann et al 1980).…”

Section: Introductionmentioning

confidence: 99%

Arylnaphthalene lactones: structures and pharmacological potentials

2021

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Natural arylnaphthalene lactones are representative lignans that are found in various dietary and medicinal plants. Their unique structural features and significant pharmacological activity have attracted considerable attention from both synthetic and medicinal chemists. Owing to their unique structural features such as relative rigid tetracyclic skeleton, structural diversity of more than five substituents, and no chiral center, arylnaphthalene lactones are recognized as a valuable scaffold for drug discovery, in addition to their significant pharmacological activities. This review covers the structures and isolation of all naturally occurring arylnaphthalene lactone congeners reported. Based on the aryl substituents, they were categorized as Type I and Type II and further classified according to the oxidation state of the ring and glycosylation level. Special attention has been paid to natural arylnaphthalene lactones owing to their broad spectrum of biological activities such as cytotoxic, antiplatelet, antiviral, anti-HIV, antifungal, neuroprotective, and anti-inflammatory properties. All the products were reorganized based on their biological activities, and selected data are presented.

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Arylnaphthalene lignans. Synthesis of justicidin E, taiwanin C, dehydrodimethylconidendrin, and dehydrodimethylretrodendrin

Abstract: interpreting the mass spectra, ir and Raman spectra, nmr spectra, and epr spectra, respectively.

Cited by 46 publications

References 2 publications

Podophyllotoxin Derivatives: Current Synthetic Approaches for New Anticancer Agents

Podophyllotoxin Derivatives: Current Synthetic Approaches for New Anticancer Agents

Two New Arylnaphthalide Lignans from Justicia flava Roots*

Arylnaphthalene lactones: structures and pharmacological potentials

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