4815-25-2Relevant academic research and scientific papers
Synthesis of novel 2-(1-adamantanylcarboxamido)thiophene derivatives. Selective cannabinoid type 2 (CB2) receptor agonists as potential agents for the treatment of skin inflammatory disease
Mugnaini, Claudia,Rabbito, Alessandro,Brizzi, Antonella,Palombi, Nastasja,Petrosino, Stefania,Verde, Roberta,Di Marzo, Vincenzo,Ligresti, Alessia,Corelli, Federico
, p. 239 - 251 (2018/10/24)
A set of CB2R ligands, based on the thiophene scaffold, was synthesized and evaluated in in vitro assays. Compounds 8c-i, k, l, bearing the 3-carboxylate and 2-(adamantan-1-yl)carboxamido groups together with apolar alkyl/aryl substituents at 5-position or at 4- and 5-positions of the thiophene ring possess high CB2R affinity at low nanomolar concentration, good receptor selectivity, and agonistic functional activity. The full agonist 8g, showing the best balance between receptor affinity and selectivity, was tested in vitro in an experimental model of allergic contact dermatitis and proved to be able to block the release of MCP-2 in HaCaT cells at 10 μM concentration.
Synthesis and pharmacological characterization of 2-(acylamino)thiophene derivatives as metabolically stable, orally effective, positive allosteric modulators of the GABAB receptor
Mugnaini, Claudia,Pedani, Valentina,Casu, Angelo,Lobina, Carla,Casti, Alberto,MacCioni, Paola,Porcu, Alessandra,Giunta, Daniela,Lamponi, Stefania,Solinas, Maurizio,Dragoni, Stefania,Valoti, Massimo,Colombo, Giancarlo,Castelli, Maria Paola,Gessa, Gian Luigi,Corelli, Federico
, p. 3620 - 3635 (2013/06/27)
Two recently reported hit compounds, COR627 and COR628, underpinned the development of a series of 2-(acylamino)thiophene derivatives. Some of these compounds displayed significant activity in vitro as positive allosteric modulators of the GABAB receptor by potentiating GTPγS stimulation induced by GABA at 2.5 and 25 μM while failing to exhibit intrinsic agonist activity. Compounds were also found to be effective in vivo, potentiating baclofen-induced sedation/hypnosis in DBA mice when administered either intraperitoneally or intragastrically. Although displaying a lower potency in vitro than the reference compound GS39783, the new compounds 6, 10, and 11 exhibited a higher efficacy in vivo: combination of these compounds with a per se nonsedative dose of baclofen resulted in shorter onset and longer duration of the loss of righting reflex in mice. Test compounds showed cytotoxic effects at concentrations comparable to or higher than those of GS39783 or BHF177.
Discovery of novel thieno[2,3-d]pyrimidin-4-yl hydrazone-based inhibitors of Cyclin D1-CDK4: Synthesis, biological evaluation, and structure-activity relationships
Horiuchi, Takao,Chiba, Jun,Uoto, Kouichi,Soga, Tsunehiko
scheme or table, p. 305 - 308 (2011/02/28)
The synthesis and evaluation of new analogues of thieno[2,3-d]pyrimidin-4-yl hydrazones are described. 2-Pyrdinecarboxaldehyde [6-(tert-butyl)thieno[2,3-d]pyrimidine-4-yl]hydrazone derivatives have been identified as cyclin-dependent kinase 4 (CDK4) inhibitors. The potency, selectivity profile, and structure-activity relationship of this series of compounds are discussed.
Gewald synthesis of 2-aminothiophenes on a soluble polymer-support
Zhang, Haiqing,Yang, Guichun,Chen, Jianian,Chen, Zuxing
, p. 360 - 361 (2007/10/03)
A variety of polysubstituted thiophenes have been prepared via a solvent-free one-pot microwave assisted Gewald reaction using poly (ethylene glycol) as a soluble polymer support.
