1056015-76-9

Upstream product

• 533-58-4 2-Iodophenol 
• 39684-80-5 2-(tert-butoxycarbonylamino)ethyl bromide 
• 26690-80-2 2-(N-tert-butoxycarbonylamino)ethanol 
• 459817-82-4 2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester 
• 71999-74-1 tert-butyl N-(2-chloroethyl)carbamate 
• 24424-99-5 di-tert-butyl dicarbonate 

Relevant academic research and scientific papers

Synthesis of Heteroaryl ortho -Phenoxyethylamines via Suzuki Cross-Coupling: Easy Access to New Potential Scaffolds in Medicinal Chemistry

Heteroaryl ortho-phenoxyethylamines have been extensively employed in medicinal chemistry as privileged scaffolds for the design of highly potent and selective ligands. Herein an efficient, fast, and general method for the synthesis of heteroaryl phenoxyethylamines via Suzuki cross-coupling is reported. This approach offers the opportunity to obtain a large variety of biaryls incorporating five-membered (thiophene, furan, thiazole, pyrazole, imidazole) or six-membered (pyridine, pyrimidine) heteroaromatic rings for appropriate libraries of ligands. All the compounds presented here have never been synthesized before and a full structural characterization is given.

Identification of a Potent and Selective 5-HT1AReceptor Agonist with in Vitro and in Vivo Antinociceptive Activity

Opioids are the gold standard drugs for the treatment of acute and chronic severe pain, although their serious side effects constitute a big limitation. In the search for new and safer drugs, 5-HT1AR agonists are emerging as potential candidates in pain relief therapy. In this work, we evaluated the affinity and activity of enantiomers of the two newly synthesized, potent 5-HT1AR agonists N-[(2,2-diphenyl-1,3-dioxolan-4-yl)methyl]-2-[2-(pyridin-4-yl)phenoxy]ethan-1-ammonium hydrogenoxalate (rac-1) and N-((2,2-diphenyl-1,3-dioxolan-4-yl)methyl)-2-(2-(1-methyl-1H-imidazol-5-yl)phenoxy)ethan-1-ammonium hydrogenoxalate (rac-2) in vitro and in vivo. The role of chirality in the interaction with 5-HT1AR was evaluated by molecular docking. The activity of the rac-1 was tested in mouse models of acute pain (hot plate) and severe tonic nociceptive stimulation (intraplantar formalin test). Rac-1 was active in the formalin test with a reduction in paw licking in both phases at 10 mg/kg, and its effect was abolished by the selective 5-HT1AR antagonist, WAY-100635. The eutomer (S)-1, but not the racemate, was active during the hot plate test at 10 and 20 mg/kg, and this effect was abolished by 30 min treatment with WAY-100635 at 30 min. Similarly to 8-OH-DPAT, (S)-1 evoked a slow outward current and depressed spontaneous glutamatergic transmission in superficial dorsal horn neurons, more effectively than rac-1. The eutomer (S)-1 showed promising developability properties, such as high selectivity over 5-HT subtypes, no interaction with the μ receptors, and low hepato- and cardiotoxicity. Therefore, (S)-1 may represent a potential candidate for the treatment of acute and chronic pain without having the adverse effects that are commonly associated with the classic opioid drugs.

Copper-catalysed cross-coupling affected by the Smiles rearrangement: A new chapter on diversifying the synthesis of chiral fluorinated 1,4-benzoxazine derivatives

Synthesis of different chiral fluorinated Boc-[1,4]benzoxazins from their open chain precursors were investigated. The NMR spectra and crystallographic data showed the presence of the Smiles Rearrangement (SR) followed by copper catalysed coupling. The in

Fluorescence and hybridization properties of peptide nucleic acid containing a substituted phenylpyrrolocytosine designed to engage guanine with an additional H-bond

A new pyrrolocytosine derivative has been designed to selectively interact with guanine and has been evaluated in peptide nucleic acid where it imparts increased selective binding affinity for complementary oligonucleotides. The modified nucleobase also possesses an exceptionally high fluorescence quantum yield that is responsive to hybridization. Copyright