113642-05-0Relevant academic research and scientific papers
Discovery and optimization of potent broad-spectrum arenavirus inhibitors derived from benzimidazole and related heterocycles
Burgeson, James R.,Moore, Amy L.,Gharaibeh, Dima N.,Larson, Ryan A.,Cerruti, Natasha R.,Amberg, Sean M.,Hruby, Dennis E.,Dai, Dongcheng
, p. 750 - 756 (2013/02/25)
A series of potent arenavirus inhibitors sharing a benzimidazole core were previously reported by our group. SAR studies were expanded beyond the previous analysis, which involved the attached phenyl rings and methylamino linker portion, to include modifications focused on the benzimidazole core. These changes included the introduction of various substituents to the bicyclic benzimidazole ring system along with alternate core heterocycles. Many of the analogs containing alternate nitrogen-based bicyclic ring systems were found to retain antiviral potency compared to the benzimidazole series from which we derived our lead compound, ST-193. In fact, 21h, built on an imidazopyridine core, possessed a near tenfold increase in potency against Lassa virus pseudotypes compared to ST-193. As found with the benzimidazole series, broad-spectrum arenavirus activity was also observed for a number of the analogs discovered during this study.
Atroposelective radical aryl migration reactions from sulfur to carbon
Schulte, Birte,Fr?hlich, Roland,Studer, Armido
experimental part, p. 11852 - 11859 (2009/04/07)
The paper describes stereoselective radical aryl migration reactions from sulfur in sulfonates to aryl radicals for the synthesis of axially chiral biaryls. A chirality center in secondary benzylic sulfonates is used to diastereoselectively (atroposelectively) install a stereogenic axis via a 1,5 aryl migration reaction. Atroposelectivity has not been investigated in stereoselective radical chemistry before. Good yields (53-82%) but low selectivities (up to 2 to 1) were obtained.
SUBSTITUTED PIPERAZINES, (1,4) DIASZEPINES, AND 2,5-DIAZABICYCLO (2.2.1) HEPTANES AS HISTAMINE H1 AND/OR H3 ANTAGONISTS OR HISTAMINE H3 REVERSE ANTAGONISTS
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Page 25-26, (2008/06/13)
The present invention relates to novel piperazine and azepine derivatives having pharmacological activity, processes for their preparation, to compositions containing them and to their use in the treatment of neurodegenerative disorders including Alzheimer's disease.
Synthesis of Benzocarbacephem and Benzocarbapenem Derivatives by Copper-promoted Intramolecular Aromatic Substitution
Joyeau, Roger,Yadav, Lal D. S.,Wakselman, Michel
, p. 1899 - 1908 (2007/10/02)
Copper-mediated cyclisation of 4-azetidinones and 4-azetidinones proved to be a route to benzocarbacephem and benzocarbapenem derivatives respectively.The effect of functionalities present in the alkyl part of the ring to be formed was considered with regard to cyclisation efficiency and further chemical modifications.Conversion, into halide, of the diastereoisomeric mixture (4R,6S; 4S,6R; 4R,6R; and 4S,6S) of t-butyl 2-hydroxybenzocarbacephem-4'-carboxylate (14f) afforded either the chloride (17a) as racemic diastereoisomers or the fluoride (17c) as a single racemic diastereoisomer.The corresponding free carboxylic acids (18a, c) were designed as inactivators of beta-lactamases.
