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Volume 68
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Scientia Pharmaceutica is published by MDPI from Volume 84 Issue 3 (2016). Previous articles were published by another publisher in Open Access under a CC-BY (or CC-BY-NC-ND) licence, and they are hosted by MDPI on mdpi.com as a courtesy and upon agreement with Austrian Pharmaceutical Society (Österreichische Pharmazeutische Gesellschaft, ÖPhG).
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Article

Thieno[2,3-b)pyridinones as Antagonists on the Glycine Site of the N-methyl-ᴅ-aspartate Receptor - Binding Studies, Molecular Modeling and structure-Activity-Relationships †

by
H.-P. Buchstaller
2,1,
C.D. Siebert
2,
R.H. Lyssy
2,
G. Ecker
3,
M. Krug
1,
M.L. Berger
4,
R. Gottschlic
1 and
C.R. Noe
2,3,*
1
Merck KGaA, D-64271 Darmstadt, Germany
2
Institute of Pharmaceutical Chemistry, Johann Wolfgang Goethe University, D-60439 Frankfurt, Germany
3
Institute of Pharmaceutical Chemistry, University of Vienna, A-1090 Wien, Austria
4
Institute of Biochemical Pharmacology, University of Vienna, A-1090 Wien, Austria
*
Author to whom correspondence should be addressed.
†
Dedicated to Univ.-Prof. Dr. W. Kubelka with our best wishes on the occasion of his 65th birthday
Sci. Pharm. 2000, 68(1), 1-14; https://doi.org/10.3797/scipharm.aut-00-01
Submission received: 18 February 2000 / Revised: 3 March 2000 / Accepted: 3 March 2000 / Published: 4 March 2000
Versions Notes

Abstract

Within the frame of the synthesis of glycine antagonists, a series of novel thieno[2,3- b]pyridinones with substituted phenyl residues in position 5 were synthesised to investigate the importance of the torsion angle between the pyridinone skeleton and the phenyl ring for binding affinity. The parent compound, 4-hydroxy-5-phenylthieno[2,3-b]pyridine-6(7H)-one, and its thienyl analogue, exhibited highest potencies, whereas compounds with ortho-substituted aryl moieties in position 5 showed decreased activities. This seems to be due to unfavourable steric interactions and increased torsion angles between the thieno[2,3- b]pyridinone system and the aryl substituent in position 5. Further evidence is drawn by QSAR studies, which showed an inverse relationship between the size of the ortho-substituent and the binding affinity.
Keywords: NMDA-receptor; glycine binding site; thieno[2,3-b]pyridinone; QSAR NMDA-receptor; glycine binding site; thieno[2,3-b]pyridinone; QSAR

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MDPI and ACS Style

Buchstaller, H.-P.; Siebert, C.D.; Lyssy, R.H.; Ecker, G.; Krug, M.; Berger, M.L.; Gottschlic, R.; Noe, C.R. Thieno[2,3-b)pyridinones as Antagonists on the Glycine Site of the N-methyl-ᴅ-aspartate Receptor - Binding Studies, Molecular Modeling and structure-Activity-Relationships. Sci. Pharm. 2000, 68, 1-14. https://doi.org/10.3797/scipharm.aut-00-01

AMA Style

Buchstaller H-P, Siebert CD, Lyssy RH, Ecker G, Krug M, Berger ML, Gottschlic R, Noe CR. Thieno[2,3-b)pyridinones as Antagonists on the Glycine Site of the N-methyl-ᴅ-aspartate Receptor - Binding Studies, Molecular Modeling and structure-Activity-Relationships. Scientia Pharmaceutica. 2000; 68(1):1-14. https://doi.org/10.3797/scipharm.aut-00-01

Chicago/Turabian Style

Buchstaller, H.-P., C.D. Siebert, R.H. Lyssy, G. Ecker, M. Krug, M.L. Berger, R. Gottschlic, and C.R. Noe. 2000. "Thieno[2,3-b)pyridinones as Antagonists on the Glycine Site of the N-methyl-ᴅ-aspartate Receptor - Binding Studies, Molecular Modeling and structure-Activity-Relationships" Scientia Pharmaceutica 68, no. 1: 1-14. https://doi.org/10.3797/scipharm.aut-00-01

APA Style

Buchstaller, H.-P., Siebert, C. D., Lyssy, R. H., Ecker, G., Krug, M., Berger, M. L., Gottschlic, R., & Noe, C. R. (2000). Thieno[2,3-b)pyridinones as Antagonists on the Glycine Site of the N-methyl-ᴅ-aspartate Receptor - Binding Studies, Molecular Modeling and structure-Activity-Relationships. Scientia Pharmaceutica, 68(1), 1-14. https://doi.org/10.3797/scipharm.aut-00-01

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