Synthesis, Antifungal Activity, and Structure−Activity Relationships of Coruscanone A Analogues

Babu, K. Suresh; Li, Xing-Cong; Jacob, Melissa R.; Zhang, Qifeng; Khan, Shabana I.; Ferreira, Daneel; Clark, Alice M.

doi:10.1021/jm061123i

Cited by 62 publications

(54 citation statements)

References 33 publications

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“…The activity of coruscanone A, which is isolated from the Peruvian pepper plant Piper coruscan, was comparable to or greater than that of amphotericin B. Coruscanone A also has a potent effect on fungal strains that are resistant to fluconazol, and it is therefore considered an alternative for the treatment of high risk immunocompromised patients and may also be of use as template for a new class of synthetic antifungal agents Babu et al, 2006). However, there have been no studies demonstrating an activity of cyclopentenediones against protozoa.…”

Section: Resultsmentioning

confidence: 99%

The leishmanicidal activity of a cyclopentenedione derivative isolated from the roots of a native Amazonian pepper (Piper carniconnectivum)

Paes-Gonçalves¹,

Facundo²,

Santos³

et al. 2012

Rev. bras. farmacogn.

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Abstract:The Piper species chemistry has been widely investigated and the phytochemical analyses have led to the isolation of a number of active compounds like alkaloids, terpenes and fl avones among others. The aim of this study was to evaluate the leishmanicidal activity of 2-[1-hydroxy-3-phenyl-(Z,2E)-2-propenylidene]-4-methyl-4-cyclopentene-1,3-dione (DCPC), a cyclopentenedione derivative isolated from the roots of Piper carniconnectivum C. DC., Piperaceae. Leishmanicidal activity against Leishmania amazonensis promastigotes was assessed, and the risk to host cell was assessed by measuring the cytotoxicity to peritoneal macrophages from BALB/c mice in vitro. L. amazonensis promastigotes and host macrophages were cultured in the presence of 100, 50, 25, 12.5 and 6 µg/mL of the cyclopentenedione derivative for up to 96 h. At the end of this period, the inhibitory concentrations (IC50) were compared with those from untreated cultures. The IC50 for promastigotes was 4.4 µg/mL after 96 h of treatment with the derivative. The 50% cytotoxic concentration (CC50) against murine peritoneal macrophages was 129 µg/mL. These results indicate that DCPC is a promising molecule for the development of leishmanicidal drugs.

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Section: Resultsmentioning

confidence: 99%

The leishmanicidal activity of a cyclopentenedione derivative isolated from the roots of a native Amazonian pepper (Piper carniconnectivum)

Paes-Gonçalves¹,

Facundo²,

Santos³

et al. 2012

Rev. bras. farmacogn.

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“…The isolated compounds were evaluated for antimicrobial (Candida albicans ATCC 90028, Escherichia coli ATCC 35218, Pseudomonas aeruginosa ATCC 27853, Mycobacterium intracellulare ATCC 23068, Aspergillus fumigat ATCC 90906, Methicillin Resistant Staphylococcus aureus ATCC 43300) ( Bharate et al, 2007 ;Babu et al, 2006 ), antileishmanial and antimalarial activity [P. falciparum (D6 clone) and P. falciparum (W2 clone)] ( Bharate et al, 2007 ).…”

Section: Antimicrobial Antileishmanial and Antimalarial Bioassaymentioning

confidence: 99%

Non-cannabinoid constituents from a high potency Cannabis sativa variety

Radwan¹,

ElSohly²,

Slade³

et al. 2008

Planta Med

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Six new non-cannabinoid constituents were isolated from a high potency Cannabis sativa L.variety, namely 5-acetoxy-6-geranyl-3-n-pentyl-1,4-benzoquinone (1), 4,5-dihydroxy-2,3,6-trimethoxy-9,10-dihydrophenanthrene (2), 4-hydroxy-2,3,6,7-tetramethoxy-9,10-dihydrophenanthrene (3), 4,7-dimethoxy-1,2,5-trihydroxyphenanthrene (4), cannflavin C (5) and β-sitosteryl-3-O-β-D-glucopyranoside-2'-O-palmitate (6). In addition, five known compounds, α-cannabispiranol (7), chrysoeriol (8), 6-prenylapigenin (9), cannflavin A (10) and β-acetyl cannabispiranol (11) were identified, with 8 and 9 being reported for the first time from cannabis. Some isolates displayed weak to strong antimicrobial, antileishmanial, antimalarial and antioxidant activities. Compounds 2-4 were inactive as analgesics.

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“…For example, a number of 2-(1H-imidazol-1-yl)-1-phenylethanone derivatives (for example 16 in Figure 2) exhibit powerful activities against C. albicans and P. chrysogenum, but moderate activity against A. niger at a concentration of 10 µg/mL [20]. In addition, (E)-2-((E)-1-methoxy-3-phenylallylidene)-4-methylcyclopent-4-ene-1,3-dione (17 in Figure 2) exhibited varying degrees of antifungal activity against fungi C. albicans ATCC 90028 (2.08 µg/mL), C. neoformans ATCC 90113 (8.33 µg/mL) and A. fumigatus ATCC 90906 (>20 µg/mL) [21]. Given these facts, it is reasonable to expect that a compound combining these two moieties may have antifungal activities.…”

Section: Introductionmentioning

confidence: 99%

Discovery of New Imidazole Derivatives Containing the 2,4-Dienone Motif with Broad-Spectrum Antifungal and Antibacterial Activity

et al. 2014

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Abstract:A compound containing an imidazole moiety and a 2,4-dienone motif with significant activity toward several fungi was discovered in a screen for new antifungal compounds. Then, a total of 26 derivatives of this compound were designed, synthesized and evaluated through in vitro and in vivo antifungal activity assays. Several compounds exhibited improved antifungal activities compared to the lead compound. Of the derivatives, compounds 31 and 42 exhibited strong, broad-spectrum inhibitory effects toward Candida spp. In particular, the two derivatives exhibited potent antifungal activities toward the fluconazole-resistant isolate C. albicans 64110, with both having MIC values of OPEN ACCESSMolecules 2014, 19 15654 8 µg/mL. In addition, they had significant inhibitory effects toward two Gram-positive bacteria, Staphylococcus aureus UA1758 (compound 31: MIC = 8 µg/mL; compound 42: MIC = 4 µg/mL) and Staphylococcus epidermidis UF843 (compound 31: MIC = 8 µg/mL; compound 42: MIC = 8 µg/mL). The results of an animal experiment indicated that both compounds could improve the survival rate of model mice infected with ATCC 90028 (fluconazole-susceptible isolate). More importantly, the two compounds exhibited notable in vivo effects toward the fluconazole-resistant C. albicans isolate, which is promising with regard to the clinical problem posed by fluconazole-resistant Candida species.

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Synthesis, Antifungal Activity, and Structure−Activity Relationships of Coruscanone A Analogues

Cited by 62 publications

References 33 publications

The leishmanicidal activity of a cyclopentenedione derivative isolated from the roots of a native Amazonian pepper (Piper carniconnectivum)

The leishmanicidal activity of a cyclopentenedione derivative isolated from the roots of a native Amazonian pepper (Piper carniconnectivum)

Non-cannabinoid constituents from a high potency Cannabis sativa variety

Discovery of New Imidazole Derivatives Containing the 2,4-Dienone Motif with Broad-Spectrum Antifungal and Antibacterial Activity

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