82413-27-2Relevant academic research and scientific papers
Highly Stereoselective Synthesis of Tetrasubstituted Acyclic All-Carbon Olefins via Enol Tosylation and Suzuki-Miyaura Coupling
Li, Beryl X.,Le, Diane N.,Mack, Kyle A.,McClory, Andrew,Lim, Ngiap-Kie,Cravillion, Theresa,Savage, Scott,Han, Chong,Collum, David B.,Zhang, Haiming,Gosselin, Francis
supporting information, p. 10777 - 10783 (2017/08/15)
A highly stereocontrolled synthesis of tetrasubstituted acyclic all-carbon olefins has been developed via a stereoselective enolization and tosylate formation, followed by a palladium-catalyzed Suzuki-Miyaura cross-coupling of the tosylates and pinacol boronic esters in the presence of a Pd(OAc)2/RuPhos catalytic system. Both the enol tosylation and Suzuki-Miyaura coupling reactions tolerate an array of electronically and sterically diverse substituents and generate high yield and stereoselectivity of the olefin products. Judicious choice of substrate and coupling partner provides access to either the E- or Z-olefin with excellent yield and stereochemical fidelity. Olefin isomerization was observed during the Suzuki-Miyaura coupling. However, under the optimized cross-coupling reaction conditions, the isomerization was suppressed to 5% in most cases. Mechanistic probes indicate that the olefin isomerization occurs via an intermediate, possibly a zwitterionic palladium carbenoid species.
1,1,2-Triphenylbut-1-enes: Relationship between Structure, Estradiol Receptor Affinity, and Mammary Tumor Inhibiting Properties
Schneider, Martin R.,Angerer, Erwin von,Schoenenberger, Helmut,Michel, Ralf Th.,Fortmeyer, H. P.
, p. 1070 - 1077 (2007/10/02)
1,1,2-Triphenylbut-1-enes, which are substituted with acetoxy groups on one, two, or three aromatic rings in the para and/or meta positions, were synthesized.The identity of the occurring E and Z isomers were established by 1H NMR spectroscopy.A study on structure-activity relationships was carried out with regard to estradiol receptor affinity and to inhibiting effects on the growth of a postmenopausal human mammary carcinoma implanted in nude mice.The para-substituted compounds generally exhibited a higher receptor affinity and a better antitumor activity than the corresponding meta-substituted ones.The E isomers were superior to the respective Z isomers in those two properties.The tumor-inhibiting effect of the mono-and disubstituted compounds was better than that of the trisubstituted ones.Except for the trisubstituted compounds, they all showed a good correlation between estradiol receptor affinity and antitumor activity.One of the compounds was also tested on the 9,10-dimethylbenzanthracene-induced, hormone-dependent mammary carcinoma of the Spraque-Dawley rat, and the results corresponded to those obtained in the xenograft tumor.
Estrogenic and Antiestrogenic Activity of Monophenolic Analogues of Tamoxifen, (Z)-2--N,N-dimethylethylamine
Ruenitz, Peter C.,Bagley, Jerome R.,Mokler, Corwin M.
, p. 1056 - 1060 (2007/10/02)
Five hydroxylated analogues of tamoxifen -N,N-dimethylethylamine> and its geometric isomer were prepared by reaction of protected hydroxy-α-ethyldeoxybenzoins with 4-phenylmagnesium bromide, followed by acid-catalyzed dehydration-deprotection and chromatographic separation of isomer mixtures.Estrogen receptor binding affinity and estrogenic and antiestrogenic activity of each of the compounds were determined in the rat, in comparison with 4-hydroxytamoxifen (2).The new compounds had a wide rangeof receptor binding affinities, with that of 3-hydroxytamoxifen (6c), the most strongly bound, approaching that of estradiol.The trans isomers 6a,b were more strongly bound than were the cis isomers 7a,b.Antiestrogenic activity was seen in all compounds except 7b.This was also true for estrogenic activity, except that in 6c this activity was also substantially reduced.Maximal antiestrogenic effectiveness of 6c occurred at a 10-fold greater daily dose (50 μg/rat) than that required for maximal effect of 2.
