40358-31-4Relevant articles and documents
Chalcone-inspired rA1/A2A adenosine receptor ligands: Ring closure as an alternative to a reactive substructure
Aucamp, Janine,Janse van Rensburg, Helena D.,Legoabe, Lesetja J.,Matthee, Chrisna,Terre’Blanche, Gisella
, (2021/12/30)
Over the past few years, great progress has been made in the development of high-affinity adenosine A1 and/or A2A receptor antagonists—promising agents for the potential treatment of Parkinson's disease. Unfortunately, many of these compounds raise structure-related concerns. The present study investigated the effect of ring closures on the rA1/A2A affinity of compounds containing a highly reactive α,β-unsaturated carbonyl system, hence providing insight into the potential of heterocycles to address these concerns. A total of 12 heterocyclic compounds were synthesised and evaluated in silico and in vitro. The test compounds performed well upon qualitative assessment of drug-likeness and were generally found to be free from potentially problematic fragments. Most also showed low/weak cytotoxicity. Results from radioligand binding experiments confirm that heterocycles (particularly 2-substituted 3-cyanopyridines) can replace the promiscuous α,β-unsaturated ketone functional group without compromising A1/A2A affinity. Structure–activity relationships highlighted the importance of hydrogen bonds in binding to the receptors of interest. Compounds 3c (rA1Ki?=?16?nM; rA2AKi?=?65?nM) and 8a (rA1Ki?=?102?nM; rA2AKi?=?37?nM), which both act as A1 antagonists, showed significant dual A1/A2A affinity and may, therefore, inspire further investigation into heterocycles as potentially safe and potent adenosine receptor antagonists.
Microwave assisted synthesis of 1,5-benzothiazepines using greener reaction medium
Kotalwar, Sanjay S.,Kale, Amol D.,Kohire, Ram B.,Jagrut, Vasant B.
, p. 993 - 996 (2019/04/05)
An efficient and eco-friendly synthesis of 1,5-benzothiazepines has been developed by the reaction of various 2-propen-1-ones with 2-aminothiophenol using microwave irradiation in greener reaction medium, glycerol. The clean reaction conditions, shorter r
A practical synthesis of 2,3-dihydro-1,5-benzothiazepines
Albanese, Domenico C. M.,Gaggero, Nicoletta,Fei, Meng
, p. 5703 - 5707 (2017/12/06)
2,3-Dihydro-1,5-benzothiazepines have been obtained through a domino process involving a Michael addition of 2-aminothiophenols to chalcones, followed by in situ cyclization. Up to 98% chemical yields have been obtained at room temperature under essential
