31891-06-2Relevant articles and documents
α,α′-N-boc-substituted Bi- and terthiophenes: Fluorescent precursors for functional materials
Dong, Yanmei,Navarathne, Daminda,Bolduc, Andreanne,McGregor, Nicholas,Skene
, p. 5429 - 5433 (2012)
Fluorescent α,α′-diamide substituted bi- and terthiophene derivatives were prepared by Stille and Suzuki couplings. Their one-pot deprotection and coupling with 2-thiophene carboxaldehyde led to stable conjugated azomethines. These exhibited electrochromic properties, and they were used to fabricate a working electrochromic device.
Synthesis of thienopyridinones via hydrazide-alkyne cyclization
Balci, Metin,Cokol, Nalan Korkmaz,Dengiz, Cagatay,Erden, Kübra,Gunay, Furkan Melih
supporting information, (2020/04/08)
A novel and efficient method for the synthesis of thieno[3,2-c]pyridinones have been developed. The synthetic strategy relies on the synthesis of halothiophene esters utilized as substrates for subsequent Sonogashira cross-coupling reactions. Hydrazinolysis of corresponding esters and following hydrazide-alkyne ring closure transformations resulted in target thienopyridinones in good yields. It is also shown that pure hydrazine monohydrate is required to facilitate the hydrazide formations.
A Thieno[2,3- d]pyrimidine Scaffold Is a Novel Negative Allosteric Modulator of the Dopamine D2 Receptor
Fyfe, Tim J.,Zarzycka, Barbara,Lim, Herman D.,Kellam, Barrie,Mistry, Shailesh N.,Katrich, Vsevolod,Scammells, Peter J.,Lane, J. Robert,Capuano, Ben
, p. 174 - 206 (2018/05/14)
Recently, a novel negative allosteric modulator (NAM) of the D2-like dopamine receptors 1 was identified through virtual ligand screening. This ligand comprises a thieno[2,3-d]pyrimidine scaffold that does not feature in known dopaminergic ligands. Herein, we provide pharmacological validation of an allosteric mode of action for 1, revealing that it is a NAM of dopamine efficacy and identify the structural determinants of this allostery. We find that key structural moieties are important for functional affinity and negative cooperativity, while functionalization of the thienopyrimidine at the 5- and 6-positions results in analogues with divergent cooperativity profiles. Successive compound iterations have yielded analogues exhibiting a 10-fold improvement in functional affinity, as well as enhanced negative cooperativity with dopamine affinity and efficacy. Furthermore, our study reveals a fragment-like core that maintains low μM affinity and robust negative cooperativity with markedly improved ligand efficiency.