ChemInform Abstract: Synthesis and Evaluation of 17α‐E‐20‐(Heteroaryl)norpregn‐1,3,5 (10),20‐tetraene‐3,17β‐diols [17α‐(Heteroaryl)vinyl Estradiols] as Ligands for the Estrogen Receptor‐α Ligand Binding Domain (ERα‐LBD).

Abstract

Synthesis and Evaluation of 17α-E-20-(Heteroaryl)norpregn-1,3,5(10),20-tetraene-3,17β-diols [17α-(Heteroaryl)vinyl Estradiols] as Ligands for the EstrogenReceptor-α Ligand Binding Domain (ERα-LBD). -A series of 17α-(heteroaryl)vinyl estradiols (III) is synthesized to evaluate the influence of heteroatom on the affinity and efficacy of estrogenic ligands for the estrogen receptor-alpha ligand binding domain. The Stille coupling strategy is chosen because Suzuki coupling between 17α-E-iodovinyl estradiol and the corresponding heteroaryl boronic acid gives no satisfying results. The reaction works with both iodo-and bromoheteroarenes. -(OLMSTED, S. L.; TONGCHAROENSIRIKUL, P.; MCCASKILL, E.; GANDIAGA, K.; LABAREE, D.; HOCHBERG, R. B.; HANSON*, R. N.; Bioorg. Med. Chem. Lett. 22 (2012) 2, 977-979, http://dx.