33797-36-3Relevant academic research and scientific papers
HETEROCYCLIC CARBOXYLIC ACIDS AS ACTIVATORS OF SOLUBLE GUANYLATE CYCLASE
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, (2016/02/18)
The present invention relates to compounds of formula I: and pharmaceutically acceptable salts thereof, wherein R1, R2, R3, R5, R6, R7, R8, R9, B, V, W, X, Y, Z and m are as defined herein. The invention also relates to pharmaceutical compositions comprising these compounds, methods of using these compounds in the treatment of various diseases and disorders, processes for preparing these compounds and intermediates useful in these processes.
Synthesis of Functionalized Dihydrobenzofurans by Direct Aryl C?O Bond Formation under Mild Conditions
Alvarado, Joseph,Fournier, Jeremy,Zakarian, Armen
, p. 11625 - 11628 (2016/10/24)
A method for the synthesis of dihydrobenzofurans by a direct aryl C?O bond formation is described. A mechanistic pathway for the reaction, distinct from previously described similar transformations, allows for mild reaction conditions that are expected to be compatible with functionalized substrates.
Navigating CYP1A Induction and Arylhydrocarbon Receptor Agonism in Drug Discovery. A Case History with S1P1 Agonists
Taylor, Simon J.,Demont, Emmanuel H.,Gray, James,Deeks, Nigel,Patel, Aarti,Nguyen, Dung,Taylor, Maxine,Hood, Steve,Watson, Robert J.,Bit, Rino A.,McClure, Fiona,Ashall, Holly,Witherington, Jason
, p. 8236 - 8256 (2015/11/09)
This article describes the finding of substantial upregulation of mRNA and enzymes of the cytochrome P450 1A family during a lead optimization campaign for small molecule S1P1 agonists. Fold changes in mRNA up to 10 000-fold for CYP1A1 in vivo
Inverting the regioselectivity of the berberine bridge enzyme by employing customized fluorine-containing substrates
Resch, Verena,Lechner, Horst,Schrittwieser, Joerg H.,Wallner, Silvia,Gruber, Karl,MacHeroux, Peter,Kroutil, Wolfgang
supporting information, p. 13173 - 13179 (2013/01/15)
Fluorine is commonly applied in pharmaceuticals to block the degradation of bioactive compounds at a specific site of the molecule. Blocking of the reaction center of the enzyme-catalyzed ring closure of 1,2,3,4- tetrahydrobenzylisoquinolines by a fluoro moiety allowed redirecting the berberine bridge enzyme (BBE)-catalyzed transformation of these compounds to give the formation of an alternative regioisomeric product namely 11-hydroxy-functionalized tetrahydroprotoberberines instead of the commonly formed 9-hydroxy-functionalized products. Alternative strategies to change the regioselectivity of the enzyme, such as protein engineering, were not applicable in this special case due to missing substrate-enzyme interactions. Medium engineering, as another possible strategy, had clear influence on the regioselectivity of the reaction pathway, but did not lead to perfect selectivity. Thus, only substrate tuning by introducing a fluoro moiety at one potential reactive carbon center switched the reaction to the formation of exclusively one regioisomer with perfect enantioselectivity. Custom-made substrates: Employing customized substrates with a fluoro atom at the normally preferred reaction site switched the regioselectivity of the berberine-bridged enzyme. With this strategy, it was possible to get access to (S)-11-hydroxy-functionalized berbines in an asymmetric fashion by using the wild-type enzyme (see scheme). Copyright
Juncunol : Revision of structure and synthesis
Cossey, Ailsa L.,Gunter, Maxwell J.,Mander, Lewis N.
, p. 3309 - 3312 (2007/10/02)
Synthetic studies have shown that juncunol is 2-hydroxy-1,7-dimethyl-5-vinyl-9,10-dihydrophenanthrene 18, and not the 1,6-dimethyl-7-vinyl isomer 2 as originally assumed.
