Solid-phase synthesis and bioevaluation of Lupeol-based libraries as antimalarial agents

Srinivasan, T.; Srivastava, Gaurav; Pathak, Arunendra; Batra, Sanjay; Raj, Kanwal; Singh, Kshipra; Puri, Sunil K.; Kundu, Bijoy

doi:10.1016/s0960-894x(02)00623-6

Cited by 39 publications

(17 citation statements)

References 16 publications

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“…lupeol from Cassia siamea Lam. Caesalpiniaceae (Ajaiyeoba et al, 2008) or lupeol-based libraries from triterpenoid lupeol (Srinivasan et al, 2002) have been shown to display antimalarial activity. In addition, piliostigmin, a 2-phenoxychromone, quercetin, quercitrin, 6-C-methylquercetin 3-methyl ether, 6-C-methylquercetin 3,7,3'-trimethyl ether, 6,8-di-C-methylkaempferol 3-methyl ether and 6,8-di-C-methylkaempferol 3,7-dimethyl ether were isolated from the leaves of P. thonningii (Ibewuike et al, 1996).…”

Section: Resultsmentioning

confidence: 99%

In vitroantiplasmodial activity and toxicity assessment of some plants from Nigerian ethnomedicine

Abiodun

Gbotosho

Ajaiyeoba

et al. 2010

Pharmaceutical Biology

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Section: Resultsmentioning

confidence: 99%

In vitroantiplasmodial activity and toxicity assessment of some plants from Nigerian ethnomedicine

Abiodun

Gbotosho

Ajaiyeoba

et al. 2010

Pharmaceutical Biology

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“…47 The use of lupeol as a scaffold for the synthesis of a library was described by Srinivasan (Scheme 31). 48 The synthesis starts with lupeol 205 been attached to a Rink amide and Sieber amide solid resin, through aliphatic dicarboxylic acid moieties. These sites also served as point to introduce chemical diversity.…”

Section: Terpenes and Steroidsmentioning

confidence: 99%

Highlights in the solid-phase organic synthesis of natural products and analogues

Eifler‐Lima¹,

Graebin²,

Uchôa³

et al. 2010

J. Braz. Chem. Soc.

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Neste trabalho nós apresentamos uma revisão sobre a síntese em fase sólida de metabólitos secundários, tais como alcalóides, poliaminas, esteróides, terpenos e flavonóides, descritos na literatura a partir de 2000. Um número considerável de rotas sintéticas elegantes e desafiadoras, usando suportes sólidos, será discutido.In this manuscript, we disclose solid-phase organic syntheses (SPOS) of small-molecules of some secondary metabolites, such as alkaloids, polyamines, steroids, terpenes, and flavonoids, described in the literature since 2000. A number of elegant, efficient and challenging syntheses on solid support will be presented.

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“…28, No. 10, 2017 derivatives, artesunate (8), artemether (9), arteether (10) and dihydroartemisinin (11), are also used in malaria chemotherapy (Figure 2). 1 Artemisins represent the key compounds in artemisinin-based combination therapy (ACT) that are presently the mainly used antimalarials.…”

Section: Introductionmentioning

confidence: 99%

“…3 Triterpenes are a class of NP with a wide distribution in plants being found in many medicinal plants and disclosing several biological effects such as anti-inflammatory, antitumor and antimalarial. 9 Among the triterpenes, lupeol (12, Figure 3) is known to have a vast occurrence in diverse plant families, like Asteraceae. Lupeol and derivatives are also of pharmaceutical interest exhibiting a broad spectrum of biological activities.…”

Section: Introductionmentioning

confidence: 99%

“…1852 a valid strategy aiming to improve the pharmacokinetic and pharmacological properties of a bioactive molecule. 9 Several NP such as alkaloids, disclose relevant biological activities, 12 as can be highlighted by the quinoline derivatives (quinine) of known antimalarial activity. 4 In this context the introduction of nitrogenated moieties in non-alkaloids NP, such as 1,2,3-triazole rings is a good strategy to obtain more active compounds.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis by Click Reactions and Antiplasmodial Activity of Lupeol 1,2,3-Triazole Derivatives

Borgati¹,

Pereira²,

Brandão³

et al. 2017

J. Braz. Chem. Soc.

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Lupeol, a triterpene frequently found in Asteraceae plant species, showed moderate to low activity in different strains of Plasmodium falciparum, the most virulent malaria etiological agents. In this work, lupeol was isolated from Parahancornia fasciculata, a plant that is used to treat malaria in the Amazonia region. In the search of more activity lupeol derivatives, five new 1,2,3-triazole hybrid molecules were synthetized by copper-catalyzed azide-alkyne cycloaddition. The antiplasmodial activity of the semi-synthetic compounds were evaluated by the lactate dehydrogenase assay; the lupeol propargyl ether was the only one to disclosing increased activity (half maximal inhibitory concentration-IC 50 -62.0 ± 1.92 μmol L ). Therefore, this work revealed a new class of interesting lupeol derivatives that can be obtained by linking electron donors to the hydroxy group at C-3.

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Solid-phase synthesis and bioevaluation of Lupeol-based libraries as antimalarial agents

Cited by 39 publications

References 16 publications

In vitroantiplasmodial activity and toxicity assessment of some plants from Nigerian ethnomedicine

In vitroantiplasmodial activity and toxicity assessment of some plants from Nigerian ethnomedicine

Highlights in the solid-phase organic synthesis of natural products and analogues

Synthesis by Click Reactions and Antiplasmodial Activity of Lupeol 1,2,3-Triazole Derivatives

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