1986
DOI: 10.1021/jm00160a020
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Conformation and activity of tetrahydrofuran lignans and analogs as specific platelet-activating-factor antagonists

Abstract: The six (racemic or meso) isomers of 3,4-dimethyl-2,5-bis(3,4-dimethoxyphenyl)tetrahydrofuran and four corresponding desmethyl analogues were prepared and assayed as inhibitors of platelet activating factor (PAF) receptor binding to rabbit platelet plasma membranes. The inhibition by these isomers is stereodependent and varies with the gross shape of the molecules as determined by the molecular mechanics program MM2. The most potent PAF antagonist in this group of compounds is trans-2,5-bis(3,4,5-trimethoxyphe… Show more

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Cited by 57 publications
(18 citation statements)
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“…1 In particular, the optically active tetrahydrofuran lignans display a wide range of pharmacological activities, including anti-parasite, [2][3][4] antibacterial, 5 antifungal, 6 antitumoral, 7 anti-inflammatory 8,9 and platelet-activating factor (PAF) inhibition. [10][11][12] Several non-symmetrical 2,5-diaryltetrahydrofuran lignans, shown in Table 1, have been isolated from Piper species (Piperaceae) containing either piperonyl, veratryl or 3,4,5-trimethoxyphenyl substituent at 2 and 5 positions and methyl groups at 3 and 4 positions attached to the tetrahydrofuran ring, as illustrated by (+)-calopiptin (1, P. schmidtii), 5-[rel-(2S,3S,4S,5S)-5'-(3'',4''-dimethoxyphenyl)-3',4'-dimethyl-2'-tetrahydro-furanyl)]-1,3-benzodioxole (2, P. wightii), (2S,3R,4S,5R)-3,4-dimethyl-2,5-bis(3',4'-dimethoxyphenyl)-tetrahydrofuran (3, P. clarkii), (±)-galgravin (4, P. futokadsura, P. hancei, P. puberculum, P.wallichii), (-)-galbelgin (5, P. attenuatum, P. futokadsura, P. thomsoni, P. wightii), (+)-grandisin (6, P. polysyphorum), (+)-machilin G (7, P. schmidtii, P. wightii), (+)-veraguensin (8, P. cuneifolium, P. futokadsura, P. puberculum) and (-)-zuonin A (9, P. schmidtii). 13 Other bis-tetrahydrofuran lignans have also been described from Achillea lingulata (Asteraceae).…”
Section: Introductionmentioning
confidence: 99%
“…1 In particular, the optically active tetrahydrofuran lignans display a wide range of pharmacological activities, including anti-parasite, [2][3][4] antibacterial, 5 antifungal, 6 antitumoral, 7 anti-inflammatory 8,9 and platelet-activating factor (PAF) inhibition. [10][11][12] Several non-symmetrical 2,5-diaryltetrahydrofuran lignans, shown in Table 1, have been isolated from Piper species (Piperaceae) containing either piperonyl, veratryl or 3,4,5-trimethoxyphenyl substituent at 2 and 5 positions and methyl groups at 3 and 4 positions attached to the tetrahydrofuran ring, as illustrated by (+)-calopiptin (1, P. schmidtii), 5-[rel-(2S,3S,4S,5S)-5'-(3'',4''-dimethoxyphenyl)-3',4'-dimethyl-2'-tetrahydro-furanyl)]-1,3-benzodioxole (2, P. wightii), (2S,3R,4S,5R)-3,4-dimethyl-2,5-bis(3',4'-dimethoxyphenyl)-tetrahydrofuran (3, P. clarkii), (±)-galgravin (4, P. futokadsura, P. hancei, P. puberculum, P.wallichii), (-)-galbelgin (5, P. attenuatum, P. futokadsura, P. thomsoni, P. wightii), (+)-grandisin (6, P. polysyphorum), (+)-machilin G (7, P. schmidtii, P. wightii), (+)-veraguensin (8, P. cuneifolium, P. futokadsura, P. puberculum) and (-)-zuonin A (9, P. schmidtii). 13 Other bis-tetrahydrofuran lignans have also been described from Achillea lingulata (Asteraceae).…”
Section: Introductionmentioning
confidence: 99%
“…are quite interesting and their synthesis has attracted considerable attention. [2][3][4][5][6][7][8][9][10][11][12][13] 2-Aryltetrahydrofuran-3,4-dicarboxylates 2 are key starting materials in the synthesis of these natural products containing tetrahydrofuran rings. Compounds 2 could also be the precursors for some natural products, such as lactones, substituted tetrahydrofurans, aryl substituted 3,7-dioxabicyclo[3.3.0]octanes 1, and so forth (Scheme 1).…”
mentioning
confidence: 99%
“…The PAF receptor antagonist L-652,731 [trans-2,5-bis(3,4,5-trimethoxyphenyl)tetrahydrofuran] was prepared and kindly supplied by Tesfaye Biftu (25).…”
mentioning
confidence: 99%