- A significant substituent effect on the regioselectivity in addition of alkynes to 3-substituted pyridines
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A substituent at the 3-position on a pyridine ring significantly affects the regioselectivity during the addition of alkynes to pyridinium salts. When the substituent is an electron-withdrawing group, 1,6-adducts are predominantly produced, whereas, 1,2-a
- Yamada, Shinji,Toshimitsu, Aya,Takahashi, Yasuko
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experimental part
p. 2329 - 2333
(2009/07/11)
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- Synthesis and receptor assay of aromatic-ethynyl-aromatic derivatives with potent mGluR5 antagonist activity
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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).
- Alagille, David,Baldwin, Ronald M.,Roth, Bryan L.,Wroblewski, Jarda T.,Grajkowska, Ewa,Tamagnan, Gilles D.
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p. 197 - 209
(2007/10/03)
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- A Novel Ethynylation of Pyridines by Reissert-Henze Type Reaction
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Reaction of N-benzoyloxypyridinium chloride, Reissert-Henze salt, with silver acetylide gave the pyridine ethynylated selectively at 2-position.The reaction is applicable to various substituted pyridines and pyridine homologs.
- Nishiwaki, Nagatoshi,Minakata, Satoshi,Komatsu, Mitsuo,Ohshiro, Yoshiki
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p. 773 - 776
(2007/10/02)
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