Antimalarial and Antiplasmodial Activities of Norneolignans. Syntheses and SAR

Skytte, Dorthe Mondrup; Nielsen, Simon Feldbæk; Chen, Ming; Zhai, Lei; Olsen, Carl Erik; Christensen, Søren Brøgger

doi:10.1021/jm0508235

Cited by 21 publications

(8 citation statements)

References 22 publications

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“…The biosynthesis, functions, and pharmacological and physiological effects of lignans have been studied, and these compounds have been shown to possess a wide range of biological activities (15,18,23). Lignans have been used as lead compounds for the development of new drugs, mainly due to their low cytotoxicity and their antiangiogenic, antiviral, antileishmanial, antifungal, hypolipidemic, and antirheumatic activities (2).…”

Section: Discussionmentioning

confidence: 99%

Antiplasmodial Activity of Aryltetralone Lignans from Holostylis reniformis

Andrade‐Neto

Silva

Lopes

et al. 2007

Antimicrob Agents Chemother

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Extracts from Holostylis reniformis were tested in vivo against Plasmodium berghei and in vitro against a chloroquine-resistant strain of Plasmodium falciparum. The hexane extract of the roots was the most active, causing 67% reduction of parasitemia in vivo. From this extract, six lignans, including a new (7R,8S,8S)-3,4-methylenedioxy-4,5-dimethoxy-2,7-cyclolignan-7-one, were isolated and tested in vitro against P. falciparum. The three most active lignans showed 50% inhibitor concentrations of <0.32 M. An evaluation of minimum lethal dose (30%) values showed low toxicity for these lignans in a hepatic cell line (Hep G2A16). Therefore, these compounds are potential candidates for the development of antimalarial drugs.

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Section: Discussionmentioning

confidence: 99%

Antiplasmodial Activity of Aryltetralone Lignans from Holostylis reniformis

Andrade‐Neto

Silva

Lopes

et al. 2007

Antimicrob Agents Chemother

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“…The neolignans constitute a class of chemical substances with described biological actions against leishmaniasis, cancer, and other diseases . Some neolignans and their derivatives have shown antimalarial activity at low concentration . Derivate 9 in this study exhibited in vitro activity, with IC 50 of 12.1 μ m , similar to other neolignan derivatives such as virolongin A (IC 50 of 14.9 μ m ) against chloroquine‐resistant P. falciparum (clone Dd2) .…”

Section: Discussionmentioning

confidence: 54%

Synthesis, antimalarial activity in vitro, and docking studies of novel neolignan derivatives

et al. 2017

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The absence of effective vaccines against malaria and the difficulties associated with controlling mosquito vectors have left chemotherapy as the primary control measure against malaria. However, the emergence and spread of parasite resistance to conventional antimalarial drugs result in a worrisome scenario making the search for new drugs a priority. In the present study, the activities of nine neolignan derivatives were evaluated as follows: (i) against blood forms of chloroquine-resistant Plasmodium falciparum (clone W2), using the tritiated hypoxanthine incorporation and anti-HRPII assays; (ii) for cytotoxic activity against cultured human hepatoma cells (HepG2); and (iii) for intermolecular interaction with the P. falciparum cysteine protease of falcipain-2 (F2) by molecular docking. The neolignan derivatives 9 and 10 showed activity against the blood form of the chloroquine-resistant P. falciparum clone W2 and were not cytotoxic against cultured human hepatoma cells. A molecular docking study of these two neolignans with FP2 revealed several intermolecular interactions that should guide the design of future analogs.

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“…[23] The elimination of the secondary alcohol generated from the reduction of keto-group of 3 b by Martin's sulfurane produced diene 12. [24] The utility of the present method is demonstrated in the short total synthesis of (+)-sporochnol A, a fish deterrent, [25] which was also synthesized by Hoveyda's group using the dihomoallyl zinc reagent (Scheme 4). [26] The tosyl protected 4hydroxyphenyl substituted allyl phosphate 14 coupled with 1isopropylcyclopropanol to yield the corresponding γ-vinyl ketone 16 in 45 % yield and 92 : 8 er, while using dimethylzinc instead of diethylzinc can improve the coupling yield to 60 % without losing enantioselectivity.…”

Section: Resultsmentioning

confidence: 90%

ProPhenol Derived Ligands to Simultaneously Coordinate a Main‐Group Metal and a Transition Metal: Application to a Zn−Cu Catalyzed Reaction

Trost

Zhang

et al. 2021

Chemistry A European J

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A new bifunctional ligand bearing chiral N-heterocyclic carbene (NHC) and prolinol moieties is presented. Utilizing the designed ligand, an in situ formed Cu/Zn heterobimetallic complex unlocks the asymmetric allylic alkylation reactions of allyl phosphates with zinc keto-homoenolates, leading to the formation of various γ-vinyl ketones with good regio-and enantio-selectivity. DF sT calculation supports that the chelation of allyl phosphates with catalyst promotes the S N 2' addition and the ligand-substrate steric interactions account for the stereoselective outcome.

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Antimalarial and Antiplasmodial Activities of Norneolignans. Syntheses and SAR

Cited by 21 publications

References 22 publications

Antiplasmodial Activity of Aryltetralone Lignans from Holostylis reniformis

Antiplasmodial Activity of Aryltetralone Lignans from Holostylis reniformis

Synthesis, antimalarial activity in vitro, and docking studies of novel neolignan derivatives

ProPhenol Derived Ligands to Simultaneously Coordinate a Main‐Group Metal and a Transition Metal: Application to a Zn−Cu Catalyzed Reaction

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