Publications (40)3.13 Total impact
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Article: 10-Hydroxydarlingine, a New Tropane Alkaloid from the Australian Proteaceous Plant Triunia erythrocarpa
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ABSTRACT: http://pubs.acs.org/doi/abs/10.1021/np9906065Journal of Natural Products 03/2000; 63(5):688–689. · 3.13 Impact Factor -
Article: The isolation and synthesis of 3-chloro-4-hydroxy-phenylacetamide produced by a plant-associated microfungus of the genus Xylaria
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ABSTRACT: Chemical investigations of the fermentation broth from the microfungus Xylaria sp. have afforded the new natural product 3-chloro-4-hydroxyphenylacetamide 1 and the previously reported fungal metabolite 3-chloro-4-hydroxyphenylacetic acid 2. This letter reports the isolation and full spectroscopic characterisation of compounds 1 and 2 by NMR, UV, IR and MS data. The crystal structure and one-pot synthesis of 3-chloro-4-hydroxyphenylacetamide are also reported. Yes Yes -
Article: 4-(2-Thienyl)-1H-pyrrole-2-carbaldehyde
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ABSTRACT: The thienyl and pyrrole rings in the molecule of the title compound, C9H7NOS, are not coplanar, their planes forming a dihedral angle of 14.7 (3)°; the C-C bond linking the rings almost coincides with the line of intersection of the planes of the rings. The molecules in the crystal structure form centrosymmetric dimeric aggregates, held together by means of N-HO hydrogen bonds. Yes Yes -
Article: Phomoxins B and C: Polyketides from an endophytic fungus of the genus Eupenicillium
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ABSTRACT: Chemical investigations of the culture broth from an endophytic fungus Eupenicillium sp. have afforded two natural products phomoxins B (1) and C (2) as well as the previously reported fungal metabolite eupenoxide (3). Compounds 1 and 2 both contain a cyclic carbonate moiety that is rare among natural products. This paper reports the full spectroscopic characterisation of phomoxins B (1) and C (2) by NMR, UV, IR and MS data. All compounds were inactive against a panel of nosocomial microbes. Yes Yes -
Article: The Synthesis of a Combinatorial Library Using a Tambjamine Natural Product Template
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Article: A Benzylisoquinoline Alkaloid from Doryphora sassafras
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Article: Xanthones from a microfungus of the genus Xylaria
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ABSTRACT: Chemical investigations of a microfungus Xylaria sp. isolated from the Australian rainforest tree Glochidion ferdinandi have afforded two new natural products, 2-hydroxy-6-methyl-8-methoxy-9-oxo-9H-xanthene-1-carboxylic acid (1) and 2-hydroxy-6-hydroxymethyl-8-methoxy-9-oxo-9H-xanthene-1-carboxylic acid (2). Compound 1 has previously been synthesised but only partially characterised. Methylation of 1 using diazomethane afforded the crystalline compound 2,8-dimethoxy-6-methyl-9-oxo-9H-xanthene-1-carboxylic acid methyl ester (3), whose structure was determined by single crystal X-ray analysis. This paper reports the full spectroscopic characterisation of compounds 1–3 by NMR, UV, IR and MS data. All compounds were inactive in a brine shrimp lethality assay and several antimicrobial screens. Yes Yes -
Article: Synthesis of the fungal natural product (-)-xylariamide A
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ABSTRACT: The first synthesis of the fungal natural product (-)-xylariamide A 1 is reported. N,O-Bis(trimethylsilyl)acetamide induced coupling of D-tyrosine with (E)-but-2-enedioic acid 2,5-dioxo-pyrrolidin-1-yl ester methyl ester 5 produced the dechloro natural product 6, which was subsequently monochlorinated using oxone and KCl to yield synthetic 1. (-)-Xylariamide A 1, (+)-xylariamide A 2 and (-)-dechloroxylariamide A 6 displayed no cytotoxic or antimicrobial activity. Yes Yes -
Article: 1H and 13C NMR assignments for two new xanthones from the endophytic fungus xylaria sp. FRR 5657
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ABSTRACT: The complete 1H and 13C NMR assignments are reported for the new natural products, 7-hydroxy-3-(hydroxymethyl)-1-methoxy-9H-xanthen-9-one (1) and 2,5-dihydroxy-8-methoxy-6-methyl-9-oxo-9H-xanthene -1-carboxylic acid (2). Both of these secondary metabolites were isolated from the fermentation culture of the endophytic fungus Xylaria sp. FRR 5657. 1D and 2D NMR experiments that included 1H, gCOSY, gHSQC and gHMBC were used for the determination of the structure and assignment of these xanthones. Copyright © 2006 John Wiley & Sons, Ltd. Yes Yes -
Article: Pim2 Inhibitors from the Papua New Guinean Plant Cupaniopsis macropetala
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Article: Synthesis and spectroscopic characteristation of a combinatoiral library based on the fungal natural product 3-chloro-4-hydroxyphenylacetamide
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ABSTRACT: Parallel solution-phase chemistry has yielded a series of secondary amide analogues of the fungal natural product 3-chloro-4-hydroxyphenylacetamide. 3-Chloro-4-hydroxyphenylacetic acid was coupled to a variety of primary amines using 1-ethyl-3-(3-dimethylamino- propyl)-carbodiimide hydrochloride. The desired products were obtained in good yield and high purity following rapid silica purification. All analogues were spectroscopically characterised using NMR, UV, IR and MS data. One compound displayed moderate cytotoxicity against the human melanoma and prostate cell lines, MM96L and DU145. Copyright © 2007 John Wiley & Sons, Ltd. Yes Yes -
Article: 4-Iodo-1H-pyrrole-2-carbaldehyde
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ABSTRACT: The title compound, C5H4INO, was synthesized during research aimed at producing suitable halogenated pyrrole building blocks for Suzuki-Miyaura coupling reactions. In the crystal structure, the molecules are planar and exhibit N-H...O bonding to form centrosymmetric dimers. Yes Yes -
Article: 2-(3-Chloro-4-hydroxylphenyl)-N-(3,4-dimethyoxyphenethyl)acetamide
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Article: The Synthesis of Two Combinatorial Libraries Using a 4-(2-Thienyl)-Pyrrole Template
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ABSTRACT: The synthesis of the novel biaryl compound, 4-(2-thienyl)-1H-pyrrole-2-carbaldehyde (1), by Suzuki–Miyaura coupling conditions is reported. Compound (1) was subsequently used as a combinatorial template in the parallel solution-phase synthesis of an amine and imine compound library. The amine library was produced using reductive amination conditions, and purification was achieved by a liquid–liquid partition followed by silica chromatography to afford ten amine analogues. The imine library consisted of five compounds, which were synthesized using volatile primary amines that allowed purification by evaporation. The synthesis of the novel and related biaryl carbaldehyde, tert-butyl-2-(5-formyl-1H-pyrrol-3-yl)-1H-pyrrole-1-carboxylate (2) is also reported. Yes Yes -
Article: Screening a natural product-based combinatorial library using FTICR mass spectrometry
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ABSTRACT: This manuscript reports the use of Fourier transform ion cyclotron resonance mass spectrometry to screen a combinatorially generated natural product-based library for binding affinity to bovine carbonic anhydrase II (bCAII). The fungal natural product 3-chloro-4-hydroxyphenylacetamide was the library template, with 11 secondary amide analogues of this template constituting the combinatorial library. 2-(3-Chloro-4-hydroxyphenyl)-N-(4-sulfamoylphenethyl)acetamide (compound 11) of this library was identified as a tight binding inhibitor of bCAII, by detection of a noncovalent complex corresponding to [bCAII + 11] in the mass spectrum. A competitive bCAII enzyme binding assay validated the mass spectrometry screening result. The equilibrium dissociation constant (Ki) for 11 was measured as 77.4 nM. Preliminary structure–activity investigations of the bioactive natural product analogue are also reported. Yes Yes -
Article: The absolute stereochemistry and cytotoxicity of the ascidian-derived metabolite, longithorone J
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ABSTRACT: The absolute stereochemistry of longithorone J (1) from the ascidian Aplidium longithorax has been determined using the advanced Mosher method. Based on biosynthetic reasoning and chiroptical data comparison the absolute stereochemistry for longithorone K (2) was also assigned. Longithorone J was tested for cytotoxicity against the cell lines SHSY5Y, HEK293T and A549. Compound 1 showed minimal cytotoxicity towards the SHSY5Y and HEK293T cell lines. Yes Yes -
Article: Determination of Analyte Concentration using the Residual Solvent Resonance in 1H NMR Spectroscopy
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Article: N-{2-[4-(Aminosulfonyl)phenyl]ethyl}-2-(4-hydroxy-phenyl)acetamide
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ABSTRACT: The crystal structure of the title sulfonamide, C16H18N2O4S, is stabilized by strong N-H...O and O-H...O intermolecular hydrogen bonds. Yes Yes -
Article: Clavatadine A, a natural product with selective recognition and irreversible inhibition of factor XIa
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Article: Antimalarial Activity of Azafluorenone Alkaloids from the Australian Tree Mitrephora diversifolia
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ABSTRACT: Mass-directed isolation of the CH2Cl2/MeOH extract from the roots of the Australian tree Mitrephora diVersifolia resulted in the purification of the new azafluorenone alkaloid 5,8-dihydroxy-6-methoxyonychine (1) together with the known natural product 5-hydroxy-6-methoxyonychine (2). The structures of 1 and 2 were determined by extensive 1D and 2D NMR and MS data analyses. Both compounds were isolated during a drug discovery program aimed at the identification of new antimalarial leads from a prefractionated natural product library. When tested against two different strains of the parasite Plasmodium falciparum (3D7 and Dd2), 2 displayed IC50 values of 9.9 and 11.4 μM, respectively, while 1 showed minimal activity. Yes Yes
