181630-93-3Relevant academic research and scientific papers
Role of the hydrogen bonding heteroatom-lys53 interaction between the p38r mitogen-activated protein (map) kinase and pyridinyl-substituted 5-membered heterocyclic ring inhibitors
Thaher, Bassam Abu,Koch, Pierre,Schattel, Verena,Laufer, Stefan
supporting information; experimental part, p. 2613 - 2617 (2010/02/28)
In the framework of investigating the role of heteroatoms in pyridinyl-substituted 5-membered (hetero)cycles as potential p38α MAP kinase inhibitor scaffolds, cyclopentene, pyrrole, furan, and imidazole analogues were synthesized and tested with respect t
SAR of 4-hydroxypiperidine and hydroxyalkyl substituted heterocycles as novel p38 Map kinase inhibitors
Revesz, Laszlo,Di Padova, Franco E.,Buhl, Thomas,Feifel, Roland,Gram, Hermann,Hiestand, Peter,Manning, Ute,Zimmerlin, Alfred G.
, p. 1261 - 1264 (2007/10/03)
The 4-hydroxypiperidine substituent was found to confer high p38 selectivity devoid of COX-1 affinity, when attached to a series of pyridinyl substituted heterocycles. Pyridinyloxazole 11 showed a promising in vivo profile with bioavailability of 64% and
An Investigation of Imidazole and Oxazole Syntheses Using Aryl-Substituted TosMIC Reagents
Sisko, Joseph,Kassick, Andrew J.,Mellinger, Mark,Filan, John J.,Allen, Andrew,Olsen, Mark A.
, p. 1516 - 1524 (2007/10/03)
This article describes efficient and mild protocols for preparing polysubstituted imidazoles in a single pot from aryl-substituted tosylmethyl isocyanide (TosMIC) reagents and imines generated in situ. Traditional imine-forming reactions employing virtually any aldehyde and amine followed by addition of the TosMIC reagent delivers 1,4,5-trisubstituted imidazoles with predictable regiochemistry. Employing chiral amines and aldehydes, particularly those derived from α-amino acids, affords imidazoles with asymmetric centers appended to N-1 or C-5 with excellent retention of chiral purity. 1,4-Disubstituted imidazoles are also readily prepared by a simple variant of the above procedure. Selecting glyoxylic acid as the aldehyde component of this procedure leads to intermediates such as 48, which readily undergo decarboxylation and elimination of the tosyl moiety to deliver 1,4-disubstituted imidazoles in high yields. Alternatively, using NH4OH as the amine component in conjunction with a variety of aldehydes delivers 4,5-disubstituted imidazoles in moderate to good yields in a single pot while avoiding the need for protecting groups. Finally, the facile preparation of mono- and disubstituted oxazoles from these TosMIC reagents and aldehydes is described.
Design and synthesis of potent, selective, and orally bioavailable tetrasubstituted imidazole inhibitors of p38 mitogen-activated protein kinase
Liverton, Nigel J.,Butcher, John W.,Claiborne, Christopher F.,Claremon, David A.,Libby, Brian E.,Nguyen, Kevin T.,Pitzenberger, Steven M.,Selnick, Harold G.,Smith, Garry R.,Tebben, Andrew,Vacca, Joseph P.,Varga, Sandor L.,Agarwal, Lily,Dancheck, Kim,Forsyth, Amy J.,Fletcher, Daniel S.,Frantz, Betsy,Hanlon, William A.,Harper, Coral F.,Hofsess, Scott J.,Kostura, Matthew,Lin, Jiunn,Luell, Sylvie,O'Neill, Edward A.,Orevillo, Chad J.,Pang, Margaret,Parsons, Janey,Rolando, Anna,Sahly, Yousif,Visco, Denise M.,O'Keefe, Stephen J.
, p. 2180 - 2190 (2007/10/03)
Novel potent and selective diarylimidazole inhibitors of p38 MAP (mitogen-activated protein) kinase are described which have activity in both cell-based assays of tumor necrosis factor-α (TNF-α) release and an animal model of rheumatoid arthritis. The SAR
Vicinal bromostannanes as novel building blocks for the preparation of di- and trisubstituted imidazoles
Revesz, Laszlo,Bonne, Frederique,Makavou, Paschalia
, p. 5171 - 5174 (2007/10/03)
Three novel imidazole-based vicinal bromostannanes 5a-c have been developed for the regioselective preparation of 2,4,5-tri- and 4,5- disubstituted imidazoles. The novel building blocks are particularly attractive for Stille and Suzuki couplings that invo
1-Substituted 4-aryl-5-pyridinylimidazoles: A new class of cytokine suppressive drugs with low 5-lipoxygenase and cyclooxygenase inhibitory potency
Boehm, Jeffrey C.,Smietana, Juanita M.,Sorenson, Margaret E.,Garigipati, Ravi S.,Gallagher, Timothy F.,Sheldrake, Peter L.,Bradbeer, Jeremy,Badger, Alison M.,Laydon, Jeffrey T.,Lee, John C.,Hillegass, Leonard M.,Griswold, Donald E.,Breton, John J.,Chabot-Fletcher, Marie C.,Adams, Jerry L.
, p. 3929 - 3937 (2007/10/03)
A series of 1-alkyl- or -aryl-4-aryl-5-pyridinylimidazoles (A) were prepared and tested for their ability to bind to a recently discovered protein kinase termed CSBP and to inhibit lipopolysaccharide (LPS)-stimulated TNF production in mice. The kinase, CS
