Marie-Claude Viaud

First synthesis of an indole glucosinolate

Abstract The synthesis of glucobrassicin, the parent structure of the indole glucosinolate family, and its desulfo-analogue is described.

Mitsunobu Thiofunctionalization-Part 2.1 an Expedient Synthesis of Aza-Heterocycle/Thiosugar Hybrids

Abstract Miscellaneous aza-heterocycle/thiosugar hydrids were synthesized from sugars through a Mitsunobu reaction involving heterocyclic mercaptans.

Identification of enzymatic degradation products from synthesized glucobrassicin by gas chromatography-mass spectrometry

Abstract Synthesized glucobrassicin, an indole glucosinolate present in rape, was submitted to exogenous enzymatic degradation with commercial myrosinase at two different pH values. Organic products were analysed after silylation by gas chromatography using a thermoionic detector. Three products (3-indolemethanol, 3-indoleacetonitrile and 3,3′-diindolylmethane) were identified by comparison with the retention times of silylated authentic materials and by gas chromatography-mass spectrometry. Two different degradation schemes were proposed according to the pH conditions: 3-indoleacetonitrile was obtained at acidic pH and 3,3′-diindolylmethane at neutral pH. The synthetic glucobrassicin thus behaved in the same manner as the natural product.

(Z)-Stereospecific Addition of Glycosylmercaptans on Nitrilium Betaines.1 Synthesis of 1-S-Glucopyranosyl Arylthiohydroximates

Abstract With a view to selecting new internal standards for HPLC analysis of glucosinolates, the synthesis of artificial desulfoglucosinolates 5 was carried out.

Synthesis and fluorescent properties of new heterobifunctional fluorescent probes

Heterobifunctional fluorescent molecules possessing the same fluorescent properties as their monofunctional parent compounds are investigated. Two different functions of these probes do not alter their lasing properties and allow many potential applications in cellular biochemistry. This paper investigates two families of compounds derived from carbazole and coumarin. The synthesis and spectral properties of these probes are described

Substituted oxygenated heterocycles and thio-analogues : Synthesis and biological evaluation as melatonin ligands

A new series of substituted oxygenated heterocycles and thio-analogues were synthesized and evaluated as melatonin receptor ligands. The replacement of the indolic moiety of melatonin by heterocyclic skeleton such as 1,4-benzodioxin, 2,3-dihydro-1,4-benzodioxin, chroman, 2,3-dihydro-1,4-benzoxathiin, thiochroman, carrying the amidic chain on the aromatic ring, leads to compounds showing a weak affinity for melatonin receptors, except for the compounds 1cb and 1hb.

Substituted pyrido[3,2-b]oxazin-3(4H)-ones: synthesis and evaluation of antinociceptive activity.

A new series of N-substituted pyrido[3,2-b]oxazinones has been synthesized, pharmacologically evaluated, and compared with acetyl salicylic acid. The compound with the maximal combination of safety and analgesic efficacy was 4-¿3-[4-(4-fluorophenyl-1-piperazinyl)propyl]¿-2H-pyrido[3,2-b]-1, 4-oxazin-3(4H)-one (6c) with ED50 values of 12.5 mg/kg po (mouse: phenylquinone writhing test) and 27.8 mg/kg po (rat: acetic acid writhing test), respectively. Compound 6c proved to be more active than aspirin with a safety index of 5.1.

A new route to 3,4-dihydro-2H-1-benzopyrans substituted at 3-position via palladium-catalysed reactions

Abstract 3,4-Dihydro-2 H -1-benzopyrans substituted at 3-position were prepared via palladium-catalysed reactions between a triflate and several coupling reagents (alkyl or aryl tin reagents and borane derivatives) according to Stille or Suzuki methodologies.

N-substituted aminohydroxypyridines as potential non-opioid analgesic agents

A series of new N-substituted aminohydroxypyridines have been synthesized, pharmacologically evaluated and compared with their N-substituted oxazolopyridone analogs. The compound with the maximal combination of safety and analgesic efficacy was 3-[2-[4-(4-fluorophenyl)-1-piperazinyl]ethyl]amino-2-hydroxypyridine (compound 10a), with ED50 values 0.4 mg kg-1 po (mouse: phenylquinone writhing test) and 0.5 mg kg-1 po (rat: acetic acid writhing test). Compound 10a possesses a potent non-opioid antinociceptive activity with moderate anti-inflammatory properties.

N,N-Disubstituted Aminomethyl Benzofuran Derivatives: Synthesis and Preliminary Binding Evaluation

A series of new N-substituted 2,3-dihydro-2-aminomethyl-2H-1-benzofuran derivatives was prepared and evaluated for affinity at 5-HT1A, 5-HT2A, 5-HT2C, 5-HT3, D2, and D3 receptors. Compound 9, 8-[4-[N-propyl-N-(7-hydroxy-2,3-dihydro -2H-1-benzofuran-2-yl)methyl]aminobutyl]-8-azaspiro[4,5]decane-7,9 -dione, bound at 5-HT1A sites with nanomolar affinity (IC50= 1.5 nM) and high selectivity over 5-HT2A, 5-HT2C, 5-HT3, D2, and D3 receptors.