Design, synthesis, and biological evaluation of a series of simple and novel potential antimalarial compounds

Ren, Hongyu; Grady, Shannon; Gamenara, Daniela; Heinzen, Horacio; Moyna, Patrick; Croft, Simon L.; Kendrick, Howard; Yardley, Vanessa; Moyna, Guillermo

doi:10.1016/s0960-894x(01)00308-0

Cited by 98 publications

(36 citation statements)

References 9 publications

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“…16 In general, the natural and synthetic tropolones have been reported to show antibacterial, antifungal, insecticidal, antiviral and antitumor activities, as well as inhibiting enzymes such as aminoglycoside-2 00 -O-adenyltransferase, 17 metalloprotease 18 and HIV-1 reverse transcriptase-associated ribonuclease H. 19 The inhibitory mechanisms of tropolones were thought to reflect their ability to form a complex with divalent cations. 20 Among these compounds, hinokitiol and its related synthetic derivatives have been reported to show antimalarial activity, whereas the synthetic benzotropolone derivatives 15,21,22 and a dihydrotroplone antibiotic, cordytropolone, 23 have also been reported to show moderate or weak antimalarial activities in vitro. However, this paper represents the first report of the antimalarial activity of carboxytropolones, such as puberulic acid.…”

Section: Discussionmentioning

confidence: 99%

In vitro and in vivo antimalarial activity of puberulic acid and its new analogs, viticolins A–C, produced by Penicillium sp. FKI-4410

et al. 2010

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In the course of screening for antimalarial agents, five tropolone compounds were isolated from the culture broth of Penicillium sp. FKI-4410. Two were known compounds, puberulic acid and stipitatic acid. Three were new analogs of puberulic acid, designated viticolins A-C. Among them, puberulic acid exhibited potent antimalarial inhibition, with IC 50 values of 0.01 lg ml À1 against chloroquine-sensitive and -resistant Plasmodium falciparum strains in vitro. Furthermore, puberulic acid showed weak cytotoxicity against human MRC-5 cells, with an IC 50 value of 57.2 lg ml À1 . The compound also demonstrated a therapeutic effect in vivo, which compared well against the currently used antimalarial drugs, and thus shows promise as a leading candidate for development into a new antimalarial compound.

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Section: Discussionmentioning

confidence: 99%

In vitro and in vivo antimalarial activity of puberulic acid and its new analogs, viticolins A–C, produced by Penicillium sp. FKI-4410

et al. 2010

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“…On the other hand, reactions with n-heptaldehyde and noctanaldehyde provided corresponding α-amidoalkyl-β-naphthols with <10% yields, the reactions didn't completed after 24 h and almost 90% of aldehydes were intact without formation aldol condensation products (Table 3, entries 23,24). We also use benzamide instead of acetamide in the mentioned reaction (Table 3, entries [18][19][20][21][22], the α-benzamidoalkyl-β-naphthol derivatives were obtained in excellent yield with short reaction times. The suggested mechanism is described in Scheme 2.…”

Section: Resultsmentioning

confidence: 99%

Three-Component Synthesis of α-Amidoalkyl-β-naphthols and α-Carbamato-alkyl-β–naphthols Catalyzed by P2O5/SiO2

Shaterian¹,

Azizi²,

Fahimi³

2012

Chem Sci Trans

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Abstract:A convenient and efficient solvent-free procedure via a three-component reaction of aldehydes, β-naphthol, and amides or carbamates for preparation of α-amidoalkyl-β-naphthols and α-carbamato-alkyl-β-naphthols in the presence of green catalytic amount of phosphorus pentoxide supported on silica gel (P 2 O 5 /SiO 2 ) is described. The use of non-toxic and inexpensive materials, simple and clean work-up, short reaction times and good yields of the products are the advantages of this method.

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“…By choosing a suitable substitution pattern, a relatively low cytotoxicity was achieved. [131] The growth of P. falciparum was inhibited by compound 52 with IC 50 = 3.2 mm compared to mammalian cells (KB cells) with IC 50 = 128 mm.…”

Section: New Artemisinin Derivatives and Peroxidesmentioning

confidence: 98%

New Antimalarial Drugs

et al. 2003

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Approximately 40% of the world population live in areas with the risk of malaria. Each year, 300-500 million people suffer from acute malaria, and 0.5-2.5 million die from the disease. Although malaria has been widely eradicated in many parts of the world, the global number of cases continues to rise. The most important reason for this alarming situation is the rapid spread of malaria parasites that are resistant to antimalarial drugs, especially chloroquine, which is by far the most frequently used. The development of new antimalarial drugs has been neglected since the 1970s owing to the end colonialism, changes in the areas of military engagement, and the restricted market potential. Only in recent years, in part supported by public funding programs, has interest in the development of antimalarial drugs been renewed. New data available from the recently sequenced genome of the malaria parasite Plasmodium falciparum and the application of methods of modern drug design promise to bring significant development in the fight against this disease.

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Design, synthesis, and biological evaluation of a series of simple and novel potential antimalarial compounds

Cited by 98 publications

References 9 publications

In vitro and in vivo antimalarial activity of puberulic acid and its new analogs, viticolins A–C, produced by Penicillium sp. FKI-4410

In vitro and in vivo antimalarial activity of puberulic acid and its new analogs, viticolins A–C, produced by Penicillium sp. FKI-4410

Three-Component Synthesis of α-Amidoalkyl-β-naphthols and α-Carbamato-alkyl-β–naphthols Catalyzed by P2O5/SiO2

New Antimalarial Drugs

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