2166-27-0Relevant articles and documents
Boron Trifluoride-Mediated Cycloaddition of 3-Bromotetrazine and Silyl Enol Ethers: Synthesis of 3-Bromo-pyridazines
Schnell, Simon D.,González, Jorge A.,Sklyaruk, Jan,Linden, Anthony,Gademann, Karl
, p. 12008 - 12023 (2021/08/24)
Pyridazines are important scaffolds for medicinal chemistry or crop protection agents, yet the selective preparation of 3-bromo-pyridazines with high regiocontrol remains difficult. We achieved the Lewis acid-mediated inverse electron demand Diels-Alder reaction between 3-monosubstituted s-tetrazine and silyl enol ethers and obtained functionalized pyridazines. In the case of 1-monosubstituted silyl enol ethers, exclusive regioselectivity was observed. Downstream functionalization of the resulting 3-bromo-pyridazines was demonstrated utilizing several cross-coupling protocols to synthesize 3,4-disubstituted pyridazines with excellent control over the substitution pattern.
Bis(arylvinyl)pyrazines, -pyrimidines, and -pyridazines As imaging agents for tau fibrils and β-Amyloid plaques in alzheimers disease models
Bolaender, Alexander,Kieser, Daniel,Voss, Constantin,Bauer, Silvia,Berger, Robert,Schmidt, Boris,Schoen, Christian,Burgold, Steffen,Bittner, Tobias,Herms, Jochen,Hoelzer, Jana,Hilger, Ingrid,Heyny-Von Haussen, Roland,Mall, Gerhard,Goetschy, Valerie,Czech, Christian,Knust, Henner
, p. 9170 - 9180,11 (2020/10/15)
The in vivo diagnosis of Alzheimers disease (AD) is of high socioeconomic interest and remains a demanding field of research. The biopathological hallmarks of the disease are extracellular plaques consisting of aggregated β-amyloid peptides (Aβ) and tau protein derived intracellular tangles. Here we report the synthesis and evaluation of fluorescent pyrazine, pyrimidine,and pyridazine derivatives in vitro and in vivo aiming at a tau-based diagnosis of AD. The probes were pre-evaluated on human brain tissue by fluorescence microscopy and were found to label all known disease-related alterations at high contrast and specificity. To quantify the binding affinity, a new thiazine red displacement assay was developed and selected candidates were toxicologically profiled. The application in transgenic mouse models demonstrated bioavailability and brain permeability for one compound. In the course of histological testing, we discovered an AD-related deposition of tau aggregates in the Bowmans glands of the olfactory epithelium, which holds potential for an endoscopic diagnosis of AD in the olfactory system.
Preparation and Diels-Alder reaction of a reactive, electron-deficient heterocyclic azadiene: Dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate. 1,2-Diazine (dimethyl 4-phenyl-1,2-diazine-3,6-dicarboxylate) and pyrrole (dimethyl 3-phenylpyrrole-2,5-dicarboxylate) introduction
Boger, Dale L.,Panek, James S.,Patel, Mona
, p. 79 - 79 (2017/05/31)
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