32460-02-9Relevant articles and documents
Thiophene-core estrogen receptor ligands having superagonist activity
Min, Jian,Wang, Pengcheng,Srinivasan, Sathish,Nwachukwu, Jerome C.,Guo, Pu,Huang, Minjian,Carlson, Kathryn E.,Katzenellenbogen, John A.,Nettles, Kendall W.,Zhou, Hai-Bing
, p. 3346 - 3366 (2013/06/04)
To probe the importance of the heterocyclic core of estrogen receptor (ER) ligands, we prepared a series of thiophene-core ligands by Suzuki cross-coupling of aryl boronic acids with bromo-thiophenes and we assessed their receptor binding and cell biological activities. The disposition of the phenol substituents on the thiophene core, at alternate or adjacent sites, and the nature of substituents on these phenols, all contribute to binding affinity and subtype selectivity. Most of the bis(hydroxyphenyl)-thiophenes were ERβ selective, whereas the tris(hydroxyphenyl)-thiophenes were ERα selective; analogous furan-core compounds generally have lower affinity and less selectivity. Some diarylthiophenes show distinct superagonist activity in reporter gene assays, giving maximal activities 2-3 times that of estradiol, and modeling suggests that these ligands have a different interaction with a hydrogen-bonding residue in helix-11. Ligand-core modification may be a new strategy for developing ER ligands whose selectivity is based on having transcriptional activity greater than that of estradiol.
Total synthesis of 5,5′,6,6′-tetrahydroxy-3,3′-biindolyl, the proposed structure of a potent antioxidant found in beetroot (Beta vulgaris)
Mee, Simon P. H.,Lee, Victor,Baldwin, Jack E.,Cowley, Andrew
, p. 3695 - 3712 (2007/10/03)
5,5′,6,6′-Tetrahydroxy-3,3′-biindolyl, the proposed structure of a phenolic antioxidant isolated from the red beetroot (Beta vulgaris), has been synthesised. The spectroscopic data of the synthetic material is not consistent with that reported for the natural product.
Synthesis of polysubstituted 3-thiofurans by regiospecific mono-ipso-substitution and ortho-metallation from 3,4-dibromofuran
Alvarez-Ibarra, Carlos,Quiroga, Maria L.,Toledano, Emilio
, p. 4065 - 4078 (2007/10/03)
The synthetic potential of 3,4-dibromofuran has been assessed by its conversion into 3,4-disubstituted furans via mono-S-ipso-substitution. The ability of 3-methylthio and 3-phenylthio substituents for directing the metallation at position α-relative to the substituent has allowed the regiospecific alkylation. It provides a straightforward approach to several 3-monothiosubstituted furans which are receiving increasing interest as odour and flavour chemicals.