223651-35-2Relevant academic research and scientific papers
Lipase-mediated resolution of substituted 2-aryl-propanols: Application to the enantioselective synthesis of phenolic sesquiterpenes
Serra, Stefano
, p. 619 - 628 (2011/07/08)
A comprehensive study of the lipase-mediated resolution of substituted 2-aryl-propanols is reported. The latter alcohols were submitted to the irreversible acetylation catalyzed either by PPL, CRL, or lipase PS. The enantioselectivity of these transformations was dependent on the type of lipase used. The type of substituents and particularly their position on the aromatic ring strongly affected the selectivity of the reaction. The experiments described prove that PPL is the more versatile lipase catalyzing the acetylation with an enantiomeric ratio (E) value that ranges from 1 up to 144, depending on the substrate used. Conversely, the same transformations were catalyzed by CRL and lipase PS with an enantiomeric ratio value, which is always less than 5. The remarkable behavior of PPL was exploited in the large scale resolution of some substituted 2-aryl-propanols whose enantiomeric forms are relevant building blocks in the enantioselective synthesis of phenolic sesquiterpenes. By these means, the synthesis of (S)-turmeronol B and the formal syntheses of (R)-curcumene, (R)-curcuphenol, (R)-xanthorrhizol, and (R)-curcuhydroquinone were accomplished.
Potent Kv1.3 inhibitors from correolide - Modification of the C18 position
Bao, Jianming,Miao, Shouwu,Kayser, Frank,Kotliar, Andrew J.,Baker, Robert K.,Doss, George A.,Felix, John P.,Bugianesi, Randal M.,Slaughter, Robert S.,Kaczorowski, Gregory J.,Garcia, Maria L.,Ha, Sookhee N.,Castonguay, Laurie,Koo, Gloria C.,Shah, Kashmira,Springer, Marty S.,Staruch, Mary Jo,Parsons, William H.,Rupprecht, Kathleen M.
, p. 447 - 451 (2007/10/03)
Correolide (1) was converted to a new series of tetracyclic Kv1.3 blockers 2. SAR for this class of compounds in two functional assays, Rb_Kv and human T cell proliferation, is presented herein. Kv1.3, the voltage-gated potassium channel in human T cells, represents a new target for treating immunosuppression and autoimmune diseases. Correolide (1), a pentacyclic natural product, is a potent and selective Kv1.3 channel blocker. Simplification of correolide via removal of its E-ring generates enone 4, whose modification produced a new series of tetracyclic Kv1.3 blockers. The structure-activity relationship for this class of compounds in two functional assays, Rb_Kv and human T cell proliferation, is presented herein. The most potent analog 43 is 15-fold more potent than correolide as inhibitor of human T cell proliferation.
Immunosuppressant tricyclic compounds
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, (2008/06/13)
The compounds of Formula I are useful as immunosuppressive agents.
Furanyl, tetracyclic triterpene derivatives with immunosuppressant activity
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, (2008/06/13)
The compounds of Formula I are useful as immunosuppressive agents.
Tetracyclic triterpene derivatives with immunosuppressant activity
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, (2008/06/13)
The compounds of Formula I are useful as immunosuppressive agents.
