Synthesis and NMDA receptor affinity of dexoxadrol analogues with modifications in position 4 of the piperidine ring

MedChemComm

Volumn 1, Issue 1, 2010, Pages 87-102

  Banerjee, Ashutosh ^a   Fröhlich, Roland ^a   Schepmann, Dirk ^a   Wünsch, Bernhard ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

2 (2,2 DIPHENYL 1,3 DIOXOLAN 4 YL) 4 METHOXYPIPERIDINE; 2 (2,2 DIPHENYL 1,3 DIOXOLAN 4 YL) N METHYLPIPERIDIN 4 AMINE; 2 (2,2 DIPHENYL 1,3 DIOXOLAN 4 YL)PIPERIDIN 4 AMINE; 2 (2,2 DIPHENYL 1,3 DIOXOLAN 4 YL)PIPERIDIN 4 OL; BENZYL 2 (2,2 DIPHENYL 1,3 DIOXOLAN 4 YL) 4 METHOXYPIPERIDINE 1 CARBOXYLATE; BENZYL 2 (2,2 DIPHENYL 1,3 DIOXOLAN 4 YL) 4 METHYLAMINOPIPERIDINE 1 CARBOXYLATE; BENZYL 4 BENZYLAMINO 2 (2,2 DIPHENYL 1,3 DIOXOLAN 4 YL)PIPERIDINE 1 CARBOXYLATE; DEXOXADROL; DIOXADROL; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; N METHYL DEXTRO ASPARTIC ACID RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG; WMS 2508;

ANIMAL CELL; ANIMAL TISSUE; ARTICLE; BINDING AFFINITY; BINDING SITE; CHEMICAL MODIFICATION; DRUG RECEPTOR BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; MOUSE; NONHUMAN; PRIORITY JOURNAL;

ALNUS;

EID: 79952514101     PISSN: 20402503     EISSN: 20402511     Source Type: Journal    
DOI: 10.1039/c0md00017e     Document Type: Article

References (30)

1. H. Bräuner-Osborne J. Egebjerg E. O. Nielsen U. Madsen P. Krogsgaard-Larsen J. Med. Chem. 2000 43 2609 2645
2. W. P. Danysz C. G. Bresink I. Quack G. Drug News Persp. 1995 261 277
3. D. Lodge, in Excitatory Amino Acid Receptors- Design of Agonists and Antagonists, ed., P. Krogsgaard-Larsen,,, J. J. Hansen,, Ellis Harwood Ltd., Chichester, 1992, pp 201 215
4. S. A. Lipton Nat. Rev. Drug Discovery 2006 5 160 170
5. W. R. Hardie J. Hidalgo I. F. Halverstadt R. E. Allen J. Med. Chem. 1966 9 127 136
6. A. E. Jacobson E. A. Harrison, Jr. M. V. Mattson M. F. Rafferty K. C. Rice J. H. Woods G. Winger R. E. Solomon R. A. Lessor J. V. Silverton J. Pharmacol. Exp. Ther. 1987 243 110 117
7. A. Thurkauf M. V. Mattson S. Richardson S. Mirsadeghi P. L. Ornstein E. A. Harrison, Jr. K. C. Rice A. E. Jacobson J. A. Monn J. Med. Chem. 1992 35 1323 1329
8. M. Aepkers B. Wünsch Bioorg. Med. Chem. 2005 13 6836 6849
9. M. Sax B. Wünsch Curr. Top. Med. Chem. 2006 6 723 732
10. M. Sax K. Ebert D. Schepmann B. Wibbeling B. Wünsch Bioorg. Med. Chem. 2006 14 5955 5962
11. M. Sax R. Fröhlich D. Schepmann B. Wünsch Eur. J. Org. Chem. 2008 6015 6028
12. G. A. Patani E. J. LaVoie Chem. Rev. 1996 96 3147 3176
13. A. J. Mancuso D. Swern Synthesis 1981 165 185
14. S. Danishefsky Acc. Chem. Res. 1981 14 400 406
15. L. Hansson R. Carlson Acta Chem. Scand. 1989 43 188 192
16. P. Buonora J. C. Olsen T. Oh Tetrahedron 2001 57 6099 6138
17. S. K. Malhotra F. Johnson J. Am. Chem. Soc. 1965 87 5493 5495
18. E. E. Sugg J. F. Griffin P. S. Portoghese J. Org. Chem. 1985 50 5032 5037
19. A. F. Abdel-Magid S. J. Mehrman Org. Process Res. Dev. 2006 10 971 1031
20. R. M. McKernan S. Castro J. A. Poat E. H. F. Wong J. Neurochem. 1989 52 777 785
21. U. Wirt D. Schepmann B. Wünsch Eur. J. Org. Chem. 2007 462 475
22. D. Schepmann B. Frehland K. Lehmkuhl B. Tewes B. Wünsch J. Pharm. Biomed. Anal. 2010 10.1016/JPBA-D-09-01731R3
23. F. I. Carroll P. Abraham K. Parham X. Bai X. Zhang G. A. Brine S. W. Mascarella B. R. Martin E. L. May C. Sauss L. Di Paolo P. Wallace J. M. Walker W. D. Bowen J. Med. Chem. 1992 35 2812 2818
24. E. L. May M. D. Aceto E. R. Bowman C. Bentley B. R. Martin L. S. Harris F. Medzihradsky M. V. Mattson A. E. Jacobson J. Med. Chem. 1994 37 3408 3418
25. C. A. Maier B. Wünsch J. Med. Chem. 2002 45 438 448
26. C. A. Maier B. Wünsch J. Med. Chem. 2002 45 4923 4930
27. R. Holl D. Schepmann R. Fröhlich R. Grünert P. J. Bednarski B. Wünsch J. Med. Chem. 2009 52 2126 2137
28. Y.-C. Cheng W. H. Prusoff Biochem. Pharmacol. 1973 22 3099 3108
29. Y. Ueda H. Nakanishi K. Yoshida Life Sci. 1999 65 1477 1484
30. M. M. Bradford Anal. Biochem. 1976 72 248 254