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p. 320-330
Received: 23 October 2001; in revised form: 18 February 2002 / Accepted: 26 February 2002 / Published: 31 March 2002
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| Download PDF Full-text (51 KB) Abstract: The synthesis and spectroscopic characterisation of some representative N -alkylsubstituted quaternary ammonium salts derived from benzothiazole, benzoxazole, benzoselenazole, indole and quinoline are described. These heterocyclic salts, bearing an activated methyl group in the 2-position in relation to the nitrogen atom and N -methyl, -pentyl, -hexyl and -decyl chains, are typical precursors of cyanine dyes.
p. 331-340
Received: 21 November 2001; in revised form: 6 March 2002 / Accepted: 15 March 2002 / Published: 31 March 2002
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| Download PDF Full-text (63 KB) Abstract: A correlation has been established between production of specific phenylphenalenones and resistance of various banana and plantain varieties towards certain pathogens. In addition a dihydrotrihydroxyphenylphenalene was isolated from the resistant 'Pelipita' plantain variety in relatively high concentrations and its structure and relative configuration were assigned on the basis of 1D and 2D NMR and NOE information. This compound is considered a key intermediate in the biosynthesis of phenylphenalenone phytoalexins.
p. 341-352
Received: 8 March 2002; in revised form: 26 March 2002 / Accepted: 27 March 2002 / Published: 31 March 2002
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| Download PDF Full-text (94 KB) Abstract: An efficient synthesis and rearrangement of 3-methyl-1,4-pentadiyne-3-ol (1) using perrhenate- and Mo(VI)-catalysts is reported. The by-products 3,6-dimethyl-1,4,7-octatriyne-3,6-diol (2) and 3-ethynyl-5-methyl-1,6-heptadiyne-3,5-diol (3) were isolated and spectroscopically characterized. A possible reaction mechanism for the formation of the byproducts is discussed.
p. 353-362
Published: 31 March 2002
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| Download PDF Full-text (104 KB) Abstract: Treatment of 5,6-dimethoxy-2-(methylphenylcarbamoyl)-benzofuran-3-carboxylic acid with PPA yielded 2,3-dimethoxy-7-methyl-7,12-dihydro-6H-[1]-benzofuro-[2,3-c]-[1]-benzazepin-6,12-dione. The analogous 2-[(5,6-dimethoxybenzofuran-2-carbonyl)methylamino]benzoic acid was resistant to cyclization, whereas 2-[(6-methoxybenzofuran-2-carbonyl)-amino]benzoic acid underwent cyclization to the corresponding 3,1-benzoxazin-4-one.
p. 363-373
Received: 24 October 2001; in revised form: 12 March 2002 / Accepted: 22 March 2002 / Published: 31 March 2002
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| Download PDF Full-text (103 KB) Abstract: Condensation of 6-chloro-, 5-tert -butyl- or 6-chloro-5-tert -butylpyrazine-2-carboxylic acid chloride with ring substituted anilines yielded a series of amides, which were tested for their in vitro antimycobacterial, antifungal and photosynthesis-inhibiting activities. The highest antituberculotic activity (72% inhibition) against Mycobacterium tuberculosis and the highest lipophilicity (log P = 6.85) were shown by the 3,5-bistrifluoromethylphenyl amide of 5-tert -butyl-6-chloropyrazine-2-carboxylic acid (2o). The 3-methylphenyl amides of 6-chloro- and 5-tert -butyl-6-chloro-pyrazine-2-carboxylic acid (2d and 2f) exhibited only a poor in vitro antifungal effect (MIC = 31.25-500 μmol·dm-3 ) against all strains tested, although the latter was the most active antialgal compound (IC50 = 0.063 mmol·dm-3 ). The most active inhibitor of oxygen evolution rate in spinach chloroplasts was the (3,5-bis-trifluoromethylphenyl)amide of 6-chloropyrazine-2-carboxylic acid (2m, IC50 = 0.026 mmol·dm-3 ).
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