5779-47-5Relevant articles and documents
Structure-Activity Relationships of Estrogenic Ligands: Synthesis and Evaluation of (17α,20E)- and (17α,20Z)-21-Halo-19-norpregna-1,3,5(10),20-tetraene-3,17β-diols
Napolitano, Elio,Fiaschi, Rita,Hanson, Robert N.
, p. 2754 - 2759 (1991)
As part our program to probe the molecular requirement for estrogen-receptor binding we undertook the synthesis and evaluation of the 17α,E and 17α,Z halovinyl estradiols.By use of an improved variation of the existing synthetic strategy, the targeted compounds were prepared stereospecifically and in 92-98percent yields from the corresponding 17α,E or 17α,Z estradiol 3-acetates.The novel estradiol derivatives were evaluated for their relative binding affinity (RBA) for the estrogen receptor with use of a rat uterine preparation.The results demonstrated a marked difference between the E and Z isomers and among the halogen employed.The Z isomers possessed significantly higher RBA values and the larger halogens (I, Br) were more effective than the smaller Cl substituent.These results modify the previous interpretations of estrogen-receptor binding for steroidal ligands.As a result, our design of (radio)halogenated ligands will incorporate this concern for Z vs E stereochemistry.
ESTRADIOL-RELATED COMPOUNDS AND METHODS OF USE AS ANTI-TUMOR AGENTS
-
Page/Page column 16, (2008/06/13)
This invention relates to new estradiol-related compounds that can be used to treat various types of cancer including prostate and breast cancers.
HYPERVALENT IODINE OXIDATION OF ETHYNYLCARBINOLS: A SHORT AND EFFICIENT CONVERSION OF DIHYDROXYACETONYL GROUPS FROM KETO GROUPS
Kita, Yasuyuki,Yakura, Takayuki,Terashi, Hiroaki,Haruta, Jun-ichi,Tamura, Yasumitsu
, p. 891 - 894 (2007/10/02)
Oxidation of ethynylcarbinols (4a-g), prepared easily from ketones, with a hypervalent iodine reagent, phenyliodosyl bis(trifluoroacetate) (PIFA), in chloroform-acetonitrile-water gave the dihydroxyacetonyl compounds (6a-g) in high yields.Keywords: phenyliodosyl bis(trifluoroacetate); ethynylcarbinol; dihydroxyacetone; terminal alkyne; α-hydroxyketone