32454-33-4Relevant articles and documents
N-Phenyl-1,2,3,4-tetrahydroisoquinoline: An Alternative Scaffold for the Design of 17β-Hydroxysteroid Dehydrogenase 1 Inhibitors
Mottinelli, Marco,Sinreih, Ma?a,Ri?ner, Tea L.,Leese, Mathew P.,Potter, Barry V. L.
, p. 259 - 291 (2020/12/07)
17β-Hydroxysteroid dehydrogenases catalyse interconversion at the C17 position between oxidized and reduced forms of steroidal nuclear receptor ligands. The type 1 enzyme, expressed in malignant cells, catalyses reduction of the less-active estrone to estradiol, and inhibitors have therapeutic potential in estrogen-dependent diseases such as breast and ovarian cancers and in endometriosis. Synthetic decoration of the nonsteroidal N-phenyl-1,2,3,4-tetrahydroisoquinoline (THIQ) template was pursued by using Pomeranz-Fritsch-Bobbitt, Pictet-Spengler and Bischler-Napieralski approaches to explore the viability of this scaffold as a steroid mimic. Derivatives were evaluated biologically in vitro as type 1 enzyme inhibitors in a bacterial cell homogenate as source of recombinant protein. Structure-activity relationships are discussed. THIQs possessing a 6-hydroxy group, lipophilic substitutions at the 1- or 4-positions in combination with N-4′-chlorophenyl substitution were most favourable for activity. Of these, one compound had an IC50 of ca. 350 nM as a racemate, testifying to the applicability of this novel approach.
α-arylation of esters catalyzed by the Pd(I) dimer [P(t-Bu)3Pd(μ-Br)]
Huang, David S.,DeLuca, Ryan J.,Hartwig, John. F.
, p. 4 - 13 (2014/04/03)
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Arylation of esters catalyzed by the Pd(I) dimer {[P(t-Bu)]PdBr}
Hama, Takuo,Hartwig, John F.
supporting information; experimental part, p. 1545 - 1548 (2009/04/07)
Conditions for the coupling of bromoarenes with esters using a single base and catalyst with improved turnover numbers are described. These general conditions were made possible by using the Pd(l) catalyst {[P(f-Bu) 3]PdBr}2. Reactions of acetates, propionates, and isobutyrates are presented, and reactions of all three classes of esters on a 10 g scale are described.
