Structure-activity relationships of kadsurenone analogues

Abstract

Kadsurenone, a specific receptor antagonist of platelet-activating factor (PAF), and its analogues were prepared from derivatives of cinnamyl alcohol and (allyloxy)phenol. Racemic kadsurenone, resolvable by a Chiralpak column at low temperatures, has an IC50 value of 2 X 10(-7) M, which is about 50% of the activity of the natural product (IC50 = 1 X 10(-7) M). The structural specificity of kadsurenone was further demonstrated by the low PAF-receptor-blocking activities of denudatin B, mirandin A, desallylkadsurenone, and the 2-epimer of kadsurenone.

Avian Repellency of Coniferyl and Cinnamyl Derivatives

“…The product was purified by column chromatography (silica gel, hexane: ethyl acetate [2: 1]), and crystallized in ether and pentane at -17°C. Melting points and proton NMR peak assignments of the synthesized products agreed with published data for 3,4-dimethoxycinnamyl alcohol and benzoate (see Kuroyanagi et al 1985, Ponpipom et al 1987.…”

“…3,4-dimethoxycinnamyl alcohol was synthesized from 3,4-dimethoxycinnamic acid following the procedure of Ponpipom et al (1987). 3,4-dimethoxycinnamyl benzoate was synthesized by benzoylating 3,4dimethoxycinnamyl alcohol using procedures identical to those used for cinnamyl benzoate.…”

Dragon's blood: Botany, chemistry and therapeutic uses

“…(2S)-4 ,5-dihydroxy-7-methoxy-8-methylflavan Camarda et al (1983), González et al (2000González et al ( , 2004 10-Hydroxy-11-methoxydracaenone Meksuriyen et al (1987), González et al (2000) 3,4,5-Trimethoxycinnamyl alcohol Ponpipom et al (1987), González et al (2000) Compound name Bioactivity References (2S)-4 ,7-Dihydroxy-8-methylflavan; 3-(4-hydroxy benzyl)-5,7-dimethoxychroman; 5,7-dihydroxy-3-(4-hydroxybenzyl)-chromone; 5,7-dihydroxy-3-(4-hydroxy benzyl)-chroman-4-one; 7-hydroxy-3-(4-hydroxybenzyl) chromone; isoliquiritigenin; liquiritigenin; xenognosin González et al (2000) Loureirin C (24) González et al (2000González et al ( , 2003 (2S)-3 ,7-Dihydroxy-4 -methoxy-8-methylflavan González et al (2000González et al ( , 2004 7-Hydroxy-3-(4-hydroxybenzyl)-8-methoxychroman;…”

Neolignan Derivatives from the Flower of Magnolia biondii Pamp. and their Effects on IL-2 expression in T-cells

“…Denudatin B is an epimer of 5'-OCH 3 on kadsurenone which has been demonstrated to block platelet-activating factor (PAF) receptor 12 . PAF has been implicated as a mediator of inflammation and anaphylaxis…”