Mallotojaponins B and C: Total Synthesis, Antiparasitic Evaluation, and Preliminary SAR Studies

Grayfer, Tatyana D.; Grellier, Philippe; Mouray, Elisabeth; Dodd, Robert H.; Dubois, Joëlle; Cariou, Kevin

doi:10.1021/acs.orglett.5b03676

Cited by 16 publications

(19 citation statements)

References 23 publications

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“…Many monomeric phloroglucinols have been investigated for their antimalarial activity, 3 − 5 and some additional dimeric compounds from M. oppositifolius have recently been shown to have trypanocidal and antileishmanial activities. 6 This paper describes the syntheses and biological evaluations of mallotojaponin C and various derivatives that were reported in 2015 in a Ph.D. dissertation 7 and complements the results in an excellent recent paper by Cariou and Dubois et al 8 …”

supporting

confidence: 70%

“… 9 , 10 The use of sodium hydroxide led to higher yields of 11 , 12 , 16 , and 17 than the use of lithium hydroxide. Compounds 11 , 8 , 11 − 14 16 , 14 − 17 17 , 18 , 19 and 18 ( 17 , 20 ) have previously been synthesized, and their structures were confirmed by MS and by comparison of their 1 H and 13 C NMR spectra with previously published spectra. Thus, treatment of 10 with 3,3-dimethylallyl bromide (prenyl bromide) in 80% aqueous ethanol with 1.1 equiv of NaOH at room temperature for 16 h gave the monoprenylated product 11 in 33% yield.…”

Section: Resultsmentioning

confidence: 87%

“…The results are presented in Table 1 , together with the data for some of the same compounds from the recent Cariou and Dubois et al paper. 8 The potencies against the two different strains of P. falciparum show similar trends, but the Dd2 strain is more sensitive to these compounds than the FcB1/Columbia strain.…”

Section: Resultsmentioning

confidence: 93%

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Synthesis and Antimalarial Activity of Mallatojaponin C and Related Compounds

et al. 2016

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The phloroglucinol mallotojaponin C (1) from Mallotus oppositifolius, which was previously shown by us to have both antiplasmodial and cytocidal activities against the malaria parasite Plasmodium falciparum, was synthesized in three steps from 2′,4′,6′-trihydroxyacetophenone, and various derivatives were synthesized in an attempt to improve the bioactivity of this class of compounds. Two derivatives, the simple prenylated phloroglucinols 12 and 13, were found to have comparable antiplasmodial activities to that of mallotojaponin C.

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supporting

confidence: 70%

Section: Resultsmentioning

confidence: 87%

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Synthesis and Antimalarial Activity of Mallatojaponin C and Related Compounds

et al. 2016

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“…Grayfer et al 68 found that the modification of the prenylated side chain of the natural product can regulate biological activity. For example, an increase in the number of prenyl units on the side chain of mallotojaponin B may enhance anti-malarial and FTase inhibitory activity.…”

Section: Aplidium Conicummentioning

confidence: 99%

An overview on natural farnesyltransferase inhibitors for efficient cancer therapy

Dai

Sun

Zhang

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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As one of the world's five terminally ills, tumours can cause important genetic dysfunction. However, some current medicines for tumours usually have strong toxic side effects and are prone to drug resistance. Studies have found that farnesyltransferase inhibitors (FTIs) extracted from natural materials have a good inhibiting ability on tumours with fewer side effects. This article describes several FTIs extracted from natural materials and clarifies the current research progress, which provides a new choice for the treatment of tumours.

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“…All three peptides inhibited chymotrypsin activity, with IC 50 values of 0.62, 2.8, and 2.3 nM, respectively, and elastase with IC 50 values of 34, 100, and 99 pM, respectively. 60)…”

Section: Phenolic Compounds Four Novel Diphenylpropanes Bussealines mentioning

confidence: 99%

Novel Bioactive Natural Products Isolated from Madagascar Plants and Marine Organisms (2009–2017)

Dai

Liu

Rakotondraibe

2018

CHEMICAL & PHARMACEUTICAL BULLETIN

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Madagascar's rain forests and tropical dry forests are home to numerous endemic plant species and the island is considered a biodiversity hotspot. About 80% of the Madagascan (Malagasy) population relies on traditional medicines that have been proven to contain a variety of biologically active compounds. In the search for bioactive compounds from Madagascan biodiversity, we accessed and collected most of the literature dealing with the isolation, structure elucidation, and biological activities of organic small molecules originating from Madagascan plants and marine organisms. Since we published the first review of this work in 2009 (Curr. Med. Chem., 17, 2010, Hou and Harinantenaina), the present paper covers the isolation, structures, and bioactivity of 182 new secondary metabolites isolated from Malagasy higher plants and marine organisms in the last seven years (2009-2017).

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Mallotojaponins B and C: Total Synthesis, Antiparasitic Evaluation, and Preliminary SAR Studies

Abstract: The first total syntheses of mallotojaponin B and C as well as several analogues have been achieved. Biological evaluation of the synthesized compounds against Plasmodium falciparum and Trypanosoma brucei have also been carried out.

Cited by 16 publications

References 23 publications

Synthesis and Antimalarial Activity of Mallatojaponin C and Related Compounds

Synthesis and Antimalarial Activity of Mallatojaponin C and Related Compounds

An overview on natural farnesyltransferase inhibitors for efficient cancer therapy

Novel Bioactive Natural Products Isolated from Madagascar Plants and Marine Organisms (2009–2017)

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