824389-35-7Relevant academic research and scientific papers
Synthesis and biological evaluation of fenobam analogs as mGlu5 receptor antagonists
Jaeschke, Georg,Porter, Richard,Buettelmann, Bernd,Ceccarelli, Simona M.,Guba, Wolfgang,Kuhn, Bernd,Kolczewski, Sabine,Huwyler, Joerg,Mutel, Vincent,Peters, Jens-Uwe,Ballard, Theresa,Prinssen, Eric,Vieira, Eric,Wichmann, Juergen,Spooren, Will
, p. 1307 - 1311 (2007)
Optimization of affinity and microsomal stability led to identification of the potent, metabolically stable fenobam analog 4l. Robust in vivo efficacy of 4l was demonstrated in four different models of anxiety. Additionally, a ligand based pharmacophore a
Synthesis and receptor assay of aromatic-ethynyl-aromatic derivatives with potent mGluR5 antagonist activity
Alagille, David,Baldwin, Ronald M.,Roth, Bryan L.,Wroblewski, Jarda T.,Grajkowska, Ewa,Tamagnan, Gilles D.
, p. 197 - 209 (2007/10/03)
Noncompetitive antagonists of the human metabotropic glutamate receptor subtype 5 (mGluR5) have been implicated as potential therapeutics for the treatment of a variety of nervous system disorders, including pain, anxiety, and drug addiction. To discover novel noncompetitive antagonists to the mGluR5, we initiated an SAR study around the known lead compounds MPEP and M-MPEP. Our results pointed out the critical role of the para position of the two aromatic rings, which leads to inactive products and permitted the discovery of potent mGluR5 antagonists (e.g., 16, 25, 28, 34 IC50 = 13.5, 11.9, 21, 15 nM, respectively). Noncompetitive antagonists of the human metabotropic glutamate receptor subtype 5 (mGluR5) have been implicated as potential therapeutics for the treatment of a variety of nervous system disorders, including pain, anxiety, and drug addiction. To discover novel noncompetitive antagonists to the mGluR5, we initiated an SAR study around the known lead compounds MPEP and M-MPEP. Our results pointed out the critical role of the para position of the two aromatic rings, which leads to inactive products and permitted the discovery of potent mGluR5 antagonists (e.g., 16, 25, 28, 34 IC50 = 13.5, 11.9, 21, 15 nM, respectively).
Double elimination protocol for the synthesis of arylene ethynylenes containing heteroaromatic rings
Orita, Akihiro,Ye, Fangguo,Babu, Govindarajulu,Ikemoto, Tomohiro,Otera, Junzo
, p. 716 - 727 (2007/10/03)
The double elimination reaction of β-substituted sulfones offers a versatile strategy for synthesis of arylene ethynylene kits containing heteroaromatic rings. A sequence of aldol reaction between α-sulfonyl carbanion and aldehyde, trapping the resulting aldolate to give β-substituted sulfone, and double elimination of this intermediate can be integrated in one pot. This protocol allows thiophene, pyridine, and ferrocene units to be accommodated in phenylene ethynylene arrays.
