- Syntheses of female sex pheromone precursors of pine sawfly species and of some structurally related methyl-branched long-chain 2-alkanols.
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3,7-Dimethyl-2-undecanol, 3,7,9-trimethyl-2-tridecanol, and 3,7, 11-trimethyl-2-tridecanol were synthesized as racemic mixtures in moderate yields. The alcohols are known precursors of the female sex pheromones of the pine sawfly species Diprion nipponica, Macrodiprion nemoralis, and Microdiprion pallipes, respectively. Stereoisomeric mixtures of 3,8,12-trimethyl-2-tridecanol, erythro-(2R,3R, 11R/S)-3,11-dimethyl-2-tetradecanol, 3,5-dimethyl-2-tetradecanol, and 5,7-dimethyl-2-tetradecanol, structurally related to sex pheromone alcohol precursors of pine sawfly species, were also synthesized in moderate yields. The key reaction in the syntheses was the ring opening of gamma-butyrolactones by using different alkyl lithiums as nucleophiles.
- Hedenstroem, Erik,Andersson, Fredrik
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p. 1237 - 1254
(2007/10/03)
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- Synthesis and pharmacological evaluation of new pyrazolidine-3,5-diones as AT1 angiotensin II receptor antagonists
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On the basis of the structure of the non-peptide receptor antagonist irbesartan, a new series of AT1 ligands was designed. In these compounds the central imidazolone nucleus of irbesartan was replaced by a pyrazolidine-3,5-dione structure. The key intermediate N-alkylpyrazolidine-3,5-diones were synthesized according to a new and general method. The most active compounds possess a spirocyclopentane ring at position 4, a linear butyl chain at position 1, and the [2'(5-tetrazolyl)biphenyl-4- yl]methyl or [2'-(benzoylaminosulfonyl)biphenyl-4-yl]methyl group at position 2. Affinity toward the AT1 and AT2 receptors was assessed by the ability of the compounds to competitively displace [3H]AII from its specific binding sites. The most active compounds, 28 and 48, displayed high affinity for the AT1 receptor, good selectivity AT1 versus AT2, and potent in vitro antagonist activity.
- Le Bourdonnec, Bertrand,Meulon, Emmanuelle,Yous, Sa?d,Goossens, Jean-Fran?ois,Houssin, Raymond,Hénichart, Jean-Pierre
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p. 2685 - 2697
(2007/10/03)
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