New acetylene based histamine H3 receptor antagonists derived from the marine natural product verongamine

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 10, 1998, Pages 1133-1138

  Ali, Syed M ^a   Tedford, Clark E ^a   Gregory, Rosilyn ^a   Yates, Stephen L ^a   Phillips, James G ^a  

^a GUILFORD PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; AMIDE; HISTAMINE H3 RECEPTOR ANTAGONIST; NATURAL PRODUCT; OXIME DERIVATIVE; UNCLASSIFIED DRUG; VERONGAMINE;

ARTICLE; BLOOD BRAIN BARRIER; DERIVATIZATION; DRUG CONFORMATION; DRUG DESIGN; DRUG PENETRATION; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; MOLECULAR MODEL; PRACTICE GUIDELINE; STRUCTURE ACTIVITY RELATION;

ACETYLENE; ANIMALS; BINDING, COMPETITIVE; DRUG DESIGN; GUINEA PIGS; HEART; HISTAMINE ANTAGONISTS; KINETICS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; OXIMES; RECEPTORS, HISTAMINE H3; STRUCTURE-ACTIVITY RELATIONSHIP; SYNAPTOSOMES; TYROSINE;

EID: 0032546517     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00181-4     Document Type: Article

References (17)

1. 1. Arrang, J. M.; Garbarg, M.; Lancelot, J. C.; Lecomte, J. M.; Pollard, H.; Robba, M. F.; Schunack, W.; Schwartz, J. C. Nature 1987, 327, 117.
2. 2. Leurs, R.; Vollinga, R. C.; Timmerman, H. Prog. Drug Res. 1995, 45, 107.
3. 3. Stark, H.; Schlicker, E.; Schunack, W. Drugs Future 1996, 21, 507.
4. 4 Phillips, J. G.; Ali, S. M. In The Histamine H3 Receptor as Target for New Drugs; Leurs, R.; Timmermen, H., Eds.; Elsevier: Amsterdam 1988; in press.
5. 5 Van der Goot, H.; Schepers, M. J. P.; Sterk, G. J.; Timmerman, H. Eur. J. Med. Chem. 1992, 27, 511.
6. 6. Clitherow, J. W.; Beswick, P.; Irving, W. J.; Scopes, D.; Barnes, J. C.; Clapham, J.; Brown, J.; Evans, D.; Hayes, A. G. Abstracts of Papers, 10th Camerino-Noordwijkerhout Symposium On Perspectives In Receptor Research, Noordwijkerhout, The Netherlands; 1995.
7. 7. Tedford, C. E.; Yates, S. L.; Pawlowski, G. P.; Nalwalk, J. W.; Hough, L. B.; Khan, M. A.; Phillips, J. G.; Durant, G. J.; Frederickson, R. C. A. J. Pharm. Exp. Ther. 1995, 275, 598.
8. 8. (a) Stark, H.; Purand, K.; Huls, A.; Ligneau, X.; Garbarg, M.; Schwartz, J. C.; Schunack, W. J. Med. Chem. 1996, 39, 1220.
9. (b) Ganellin, C. R.; Hosseini, S. K.; Khalaf, Y. S.; Tertiuk, W.; Arrang, J. M.; Garbarg, M.; Ligneau, X.; Schwartz, J. C. J. Med. Chem. 1995, 38, 3342.
10. (c) Ganellin, C. R.; Andersen, B. B.; Khalaf, Y. S.; Arrang, J. M.; Garbarg, M.; Ligneau, X.; Rouleau, A.; Schwartz, J. C. Bioorg. Med. Chem. Lett. 1992, 2, 1231.
11. 9. Mierzwa, R.; King, A.; Conover, M. A.; Tozzi, S.; Puar, M. S.; Patel, M.; Coval, S. J.; Pomponi, S. A. J. Nat. Prod. 1994, 57, 175.
12. 10. The energy minimized conformations of 5 and 6 shown in Figure 1 were obtained using Tripos force field calculations (Sybyl 6.2).
13. 11. Topliss, J. G. J. Med. Chem. 1972, 15, 1006.
14. 12. (a) Phillips, J. G.; Tedford, C. E.; Yates, S. L.; Pawlowski, G. P.; Khan, M. A.; Fadnis, L.; Gregory, R.; Nikiforovich, G. Abstracts of Papers, Medicinal Chemistry Gordon Conference; New Hampshire; 1996, Poster presentation.
15. (b) Phillips, J. G.; Tedford, C. E.; Yates, S. L.; Pawlowski, G. P.; Khan, M. A.; Fadnis, L.; Gregory, R.; Nikiforovich, G.; Ali, S. Presented at 11th Camerino-Noordwijkerhout Symposium On Perspectives In Receptor Research, Noordwijkerhout, The Netherlands, 1997.
16. 13 Taylor, S. J.; Michel, A. D.; Kilpatrick, G. J. Biochem. Pharmacol. 1992, 44, 1261.
17. 14 Seyedi, N.; Win, T.; Lander H. M.; Levi, R. Circulation Res. 1997, 81, 774.