766-81-4Relevant articles and documents
Bis(het)aryl-1,2,3-triazole quinuclidines as α7 nicotinic acetylcholine receptor ligands: Synthesis, structure affinity relationships, agonism activity, [18F]-radiolabeling and PET study in rats
Ouach, Aziz,Vercouillie, Johnny,Bertrand, Emilie,Rodrigues, Nuno,Pin, Frederic,Serriere, Sophie,Boiaryna, Liliana,Chartier, Agnes,Percina, Nathalie,Tangpong, Pakorn,Gulhan, Zuhal,Mothes, Celine,Deloye, Jean-Bernard,Guilloteau, Denis,Page, Guylene,Suzenet, Franck,Buron, Frederic,Chalon, Sylvie,Routier, Sylvain
, p. 449 - 469 (2019/07/03)
In this paper we describe the design and synthesis of bis(Het)Aryl-1,2,3-triazole quinuclidine α7R ligands using an efficient three-step sequence including a Suzuki-Miyaura cross coupling reaction with commercially available and home-made boron derivatives. The exploration of SAR required the preparation of uncommon boron derivatives. Forty final drugs were tested for their ability to bind the target and nine of them exhibited Ki values below nanomolar concentrations. The best scores were always obtained when the 5-phenyl-2-thiophenyl core was attached to the triazole. The selectivity of these compounds towards the nicotinic α4β2 and serotoninergic 5HT3 receptors was assessed and their brain penetration was quantified by the preparation and in vivo evaluation of two [18F] radiolabelled derivatives. It can be expected from our results that some of these compounds will be suitable for further developments and will have effects on cognitive disorders.
Metal-free synthesis of imidazole by BF3·Et2O promoted denitrogenative transannulation of N-sulfonyl-1,2,3-triazole
Yang, Dongdong,Shan, Lihong,Xu, Ze-Feng,Li, Chuan-Ying
, p. 1461 - 1464 (2018/03/08)
BF3·Et2O promoted metal-free denitrogenative transannulation of N-sulfonyl-1,2,3-triazole was reported. Rather than transition metals, BF3·Et2O was employed for the first time to promote the formation of α-diazoimines from N-sulfonyl-1,2,3-triazoles in nitriles, leading to the synthesis of various imidazoles. The protocol tolerates a broad range of functional groups and could also be applied to the late-stage modification of bioactive molecules, demonstrating the potential of this protocol in organic synthesis. A plausible mechanism was proposed.
Palladium-catalyzed tandem C-H functionalization/cyclization strategy for the synthesis of 5-hydroxybenzofuran derivatives
Ichake, Sachin S.,Konala, Ashok,Kavala, Veerababurao,Kuo, Chun-Wei,Yao, Ching-Fa
, p. 54 - 57 (2017/11/28)
A palladium-catalyzed benzoquinone C-H functionalization/ cyclization strategy with terminal alkynes was employed for the synthesis of some biologically relevant 2, 3-disubstituted 5-hydroxybenzofuran derivatives. The benzoquinone acts as a reactant as well as an oxidant. During the process, an additional alkyne functionality can be introduced at the C3 position of the benzofuran. Base, ligand, and external oxidant are not required in this protocol.
