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Literature DB >> 17336520

Design and synthesis of novel heterobiaryl amides as metabotropic glutamate receptor subtype 5 antagonists.

Abstract

A series of heterobiaryl amides was designed and synthesized as novel mGluR5 antagonists. The synthesis using palladium catalyzed Suzuki-Miyaura cross-coupling reactions provided an array of compounds with a range of in vitro activities. In particular, compound 9e, 4(3,5-difluorophenyl)-N-(6-methylpyridin-1-yl)picolinamide, exhibited nanomolar affinity at the mGluR5 and will serve as a template for future drug design.

Entities: Chemical Disease Gene

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Year: 2007 PMID： 17336520 PMCID： PMC1924965 DOI： 10.1016/j.bmcl.2006.12.083

Source DB: PubMed Journal: Bioorg Med Chem Lett ISSN： 0960-894X Impact factor: 2.823

26 in total

Review 1. Discovery and characterization of non-competitive antagonists of group I metabotropic glutamate receptors.

Authors: F Gasparini; P Floersheim; P J Flor; M Heinrich; W Inderbitzin; D Ott; A Pagano; C Stierlin; N Stoehr; I Vranesic; R Kuhn
Journal: Farmaco Date: 2001 Jan-Feb

2. A close structural analog of 2-methyl-6-(phenylethynyl)-pyridine acts as a neutral allosteric site ligand on metabotropic glutamate receptor subtype 5 and blocks the effects of multiple allosteric modulators.

Authors: Alice L Rodriguez; Yi Nong; Nishant K Sekaran; David Alagille; Gilles D Tamagnan; P Jeffrey Conn
Journal: Mol Pharmacol Date: 2005-09-09 Impact factor: 4.436

3. Comparison of the binding pockets of two chemically unrelated allosteric antagonists of the mGlu5 receptor and identification of crucial residues involved in the inverse agonism of MPEP.

Authors: Pari Malherbe; Nicole Kratochwil; Andreas Mühlemann; Marie-Thérèse Zenner; Christophe Fischer; Martin Stahl; Paul R Gerber; Georg Jaeschke; Richard H P Porter
Journal: J Neurochem Date: 2006-07 Impact factor: 5.372

4. Design and synthesis of noncompetitive metabotropic glutamate receptor subtype 5 antagonists.

Authors: Santosh S Kulkarni; Barbara Nightingale; Christina M Dersch; Richard B Rothman; Amy Hauck Newman
Journal: Bioorg Med Chem Lett Date: 2006-05-05 Impact factor: 2.823

5. Substituent effects of N-(1,3-diphenyl-1H-pyrazol-5-yl)benzamides on positive allosteric modulation of the metabotropic glutamate-5 receptor in rat cortical astrocytes.

Authors: Tomas de Paulis; Kamondanai Hemstapat; Yelin Chen; Yongqin Zhang; Samir Saleh; David Alagille; Ronald M Baldwin; Gilles D Tamagnan; P Jeffrey Conn
Journal: J Med Chem Date: 2006-06-01 Impact factor: 7.446

6. Metabotropic glutamate 5 receptor antagonism is associated with antidepressant-like effects in mice.

Authors: Xia Li; Anne B Need; Melvyn Baez; Jeffrey M Witkin
Journal: J Pharmacol Exp Ther Date: 2006-06-27 Impact factor: 4.030

7. Catalysts for Suzuki-Miyaura coupling processes: scope and studies of the effect of ligand structure.

Authors: Timothy E Barder; Shawn D Walker; Joseph R Martinelli; Stephen L Buchwald
Journal: J Am Chem Soc Date: 2005-04-06 Impact factor: 15.419

Review 8. Therapeutic implications of the mGluR theory of fragile X mental retardation.

Authors: M F Bear
Journal: Genes Brain Behav Date: 2005-08 Impact factor: 3.449

9. Suppression of two major Fragile X Syndrome mouse model phenotypes by the mGluR5 antagonist MPEP.

Authors: Q J Yan; M Rammal; M Tranfaglia; R P Bauchwitz
Journal: Neuropharmacology Date: 2005-07-27 Impact factor: 5.250

10. Synthesis and structure-activity relationships of 3-[(2-methyl-1,3-thiazol-4-yl)ethynyl]pyridine analogues as potent, noncompetitive metabotropic glutamate receptor subtype 5 antagonists; search for cocaine medications.

Authors: Yasuyoshi Iso; Ewa Grajkowska; Jarda T Wroblewski; Jared Davis; Nicholas E Goeders; Kenneth M Johnson; Subramaniam Sanker; Bryan L Roth; Werner Tueckmantel; Alan P Kozikowski
Journal: J Med Chem Date: 2006-02-09 Impact factor: 7.446

9 in total

1. Discovery of heterobicyclic templates for novel metabotropic glutamate receptor subtype 5 antagonists.

Authors: Santosh S Kulkarni; Amy Hauck Newman
Journal: Bioorg Med Chem Lett Date: 2007-03-24 Impact factor: 2.823

2. Structure-activity relationships comparing N-(6-methylpyridin-yl)-substituted aryl amides to 2-methyl-6-(substituted-arylethynyl)pyridines or 2-methyl-4-(substituted-arylethynyl)thiazoles as novel metabotropic glutamate receptor subtype 5 antagonists.

Authors: Santosh S Kulkarni; Mu-Fa Zou; Jianjing Cao; Jeffrey R Deschamps; Alice L Rodriguez; P Jeffrey Conn; Amy Hauck Newman
Journal: J Med Chem Date: 2009-06-11 Impact factor: 7.446

3. Synthesis and SAR of novel, non-MPEP chemotype mGluR5 NAMs identified by functional HTS.

Authors: Ya Zhou; Alice L Rodriguez; Richard Williams; C David Weaver; P Jeffrey Conn; Craig W Lindsley
Journal: Bioorg Med Chem Lett Date: 2009-10-28 Impact factor: 2.823

4. Structure-activity relationships in a novel series of 7-substituted-aryl quinolines and 5-substituted-aryl benzothiazoles at the metabotropic glutamate receptor subtype 5.

Authors: Peng Zhang; Mu-Fa Zou; Alice L Rodriguez; P Jeffrey Conn; Amy Hauck Newman
Journal: Bioorg Med Chem Date: 2010-03-27 Impact factor: 3.641

5. Recent advances in the design and development of novel negative allosteric modulators of mGlu(5).

Authors: Kyle A Emmitte
Journal: ACS Chem Neurosci Date: 2011-08-17 Impact factor: 4.418

6. Design and synthesis of substituted N-(1,3-diphenyl-1H-pyrazol-5-yl)benzamides as positive allosteric modulators of the metabotropic glutamate receptor subtype 5.

Authors: Mu-Fa Zou; Jianjing Cao; Alice L Rodriguez; P Jeffrey Conn; Amy Hauck Newman
Journal: Bioorg Med Chem Lett Date: 2010-12-28 Impact factor: 2.823