106403-98-9Relevant academic research and scientific papers
Synthesis of α-methylstilbenes using an aqueous Wittig methodology and application toward the development of potent human aromatase inhibitors
Nielsen, Alexander J.,Raez-Villanueva, Sergio,Crankshaw, Denis J.,Holloway, Alison C.,McNulty, James
supporting information, p. 1395 - 1398 (2019/04/03)
The development of aqueous Wittig methodology for the synthesis of α-methylstilbenes using tripropylphosphine-derived phosphonium salts is described. The Wittig olefination reaction was high yielding and allowed isolation of stilbenes by simple filtration and washing with water. The novel phosphonium salts employed were accessed via a highly efficient, regioselective addition of hydrogen bromide to styrenes. Application of the α-methylstilbenes toward the synthesis of a collection of stilbenoid-triazoles is reported and their inhibition of CYP450 19A1 (aromatase) investigated. The overall structure-activity profile provided additional evidence on the aryl halide-ketone bioisostere hypothesis and identified 6c as a potent inhibitor of aromatase in vitro (Ki = 8 nM).
Catalytic asymmetric bromoetherification and desymmetrization of olefinic 1,3-diols with C2-symmetric sulfides
Ke, Zhihai,Tan, Chong Kiat,Chen, Feng,Yeung, Ying-Yeung
, p. 5627 - 5630 (2014/05/06)
An enantioselective and highly diastereoselective bromoetherification and desymmetrization of olefinic 1,3-diols has been developed using a C 2-symmetric cyclic sulfide catalyst. This methodology has been successfully applied to the synthesis of the key intermediate of an orally active antifungal drug posaconazole (Noxafil).
