152835-32-0Relevant academic research and scientific papers
Structure-activity relationships of the estrogenic sesquiterpene ester ferutinin. Modification of the terpenoid core
Appendino, Giovanni,Spagliardi, Paola,Sterner, Olov,Milligan, Stuart
, p. 1557 - 1564 (2007/10/03)
Esterification of p-hydroxybenzoic acid, a very weak estrogenic compound, with the daucane alcohol jaeschkeanadiol (1b) leads to a spectacular magnification of the estrogenic activity. To identify the structural elements responsible for this effect, the terpenoid core of jaeschkeanadiol p-hydroxybenzoate (ferutinin, 1a) was modified, capitalizing on the presence of two functionalities, the monoacylated, hydrogen-bonded 1,3-diol system and the double bond. The hydrogen bonding, while possibly useful, was not critical for activity, while hydrogenation and cyclopropanation of the double bond were tolerated. Conversely, oxidative modifications of the double bond that placed a hydroxyl on the α-face of the molecule proved detrimental. Taken together, these observations identified the substitution at C-8/C-9 as critical for activity.
Daucane phytoestrogens: A structure-activity study
Appendino, Giovanni,Spagliardi, Paola,Cravotto, Giancarlo,Pocock, Victoria,Milligan, Stuart
, p. 1612 - 1615 (2007/10/03)
The estrogenic activity of a series of analogues of the daucane ester ferutinin (1a) modified at the acyl moiety was investigated in a yeast screen containing the human estrogen receptor α. Rather strict structure - activity relationships were observed. T
PROSTANOIDS. LVIII. NEW α,ω-NORANALOGS OF PROSTAGLANDINS FROM FERUTINOL
Tolstikov, G. A.,Akbutina, F. A.,Dembitskii, A. D.,Valeev, F. A.,Miftakhov, M. S.
, p. 1666 - 1673 (2007/10/02)
The chemical transformations of ferutinol aimed at the construction of structures that are of pharmacological interest were studied.
