103493-56-7Relevant academic research and scientific papers
Synthesis and PGE2 inhibitory activity of novel diarylheptanoids
McLane, Richard D.,Le Cozannet-Laidin, Léon,Boyle, Maxwell S.,Lanzillotta, Lindsey,Taylor, Zachary L.,Anthony, Sarah R.,Tranter, Michael,Onorato, Amber J.
, p. 334 - 338 (2018/02/15)
Prostaglandin E2 (PGE2) is a lipid mediator of inflammation and its inhibition has become a popular drug target due to its harmful physiological roles. Diarylheptanoids are one class of compounds that have shown successful inhibition of PGE2. This paper reports the synthesis and PGE2 inhibitory activity of a series of analogues of a naturally occurring diarylheptanoid. The most efficacious compounds were examined for dose-dependent PGE2 inhibition. Among several promising compounds, the lead candidate exhibited an IC50 value of 0.56 ng/μL or 1.7 μM with no detectable toxicity at the highest dose of 10 ng/μL.
A short and efficient synthesis of a novel diarylheptanoid isolated from pleuranthodium racemigerum
Chang, Ching-Yao
, p. 286 - 289 (2011/10/13)
The first total synthesis of the linear diarylheptanoid 1-(4"-methoxyphenyl)-7-(4′-hydroxyphenyl)-(E)-hept-2-ene, which has a uniquely nonconjugated olefin, was achieved. The synthetic route employed an olefin cross-metathesis as a key step. Beginning wit
Studies on the Synthesis of Aphidicolin. Preparation of Aromatic Precursors for Spirocyclic Dienone Formation
Bell, Vivien L.,Giddings, Peter J.,Holmes, Andrew B.,Mock, Graham A.,Raphael, Ralph A.
, p. 1515 - 1522 (2007/10/02)
Novel syntheses of the alkanediones (12; R=Me, or CH2Ph) and the corresponding epoxides (13) are described.Attempts to cyclise these compounds to the spirocyclic dienone (4) were unsuccessful.Model studies on the phenolic keto cyano toluene-p-sulphonate (24) showed that the cyclopropane(25) was formed preferentially.A variety of related model compounds (29), (31), (32), and (37) were prepared and studied, but none could be cyclised to spirocyclic dienones.
FLASH VACUUM THERMOLYSIS OF SPIROCYCLOHEXADIENONES
Jenneskens, Leonardus W.,Wolf, Willem H. De,Bickelhaupt, Friedrich
, p. 3779 - 3784 (2007/10/02)
In an attempt to prepare short-bridged hydroxymetacyclophanes 1b-d, the spirocyclohexadienones 2b-d were pyrolyzed by flash vacuum thermolysis (FVT).Instead of 1b-d,variable amounts of 4-(5-hexenyl)phenol (4b) , β-hydroxybenzocycloalkenes (5b-d) and 4-(trans-1-alkenyl)phenols (6c-d) were obtained.The formation of these products is explained by invoking cleavage of a spiro bond in 2 under formation of the intermediate diradical 3 which, depending on the length of the aliphatic chain and on the temperature, has several pathways open for isomerization to spin-paired products.
