Design, synthesis, and structure-activity relationships of acetylene- based histamine H3 receptor antagonists

Journal of Medicinal Chemistry

Volumn 42, Issue 5, 1999, Pages 903-909

  Ali, Syed M ^a   Tedford, Clark E ^a   Gregory, Rosilyn ^a   Handley, Michael K ^a   Yates, Stephen L ^a   Hirth, Walter W ^a   Phillips, James G ^a  

^a GUILFORD PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; HISTAMINE H3 RECEPTOR ANTAGONIST;

ARTICLE; DRUG DESIGN; DRUG POTENCY; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; RECEPTOR AFFINITY; RECEPTOR BINDING; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ACETYLENE; ANIMALS; CEREBRAL CORTEX; DRUG DESIGN; HISTAMINE ANTAGONISTS; IMIDAZOLES; RATS; RECEPTORS, HISTAMINE H3; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0033545582     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm980310g     Document Type: Article

References (34)

1. 3) of histamine receptors. Nature 1983, 302, 832-837.
2. 3 receptors. Nature 1987, 327, 117-123.
3. 3 receptors control histamine release in human brain. J. Neurochem. 1988, 51, 105-108.
4. 3 receptors. Neuroscience 1987, 23, 149-157.
5. Mochizuki, T.; Yamatodani, A.; Okakura, K.; Takemura, M.; Inagakin, N.; Wada, H. In vivo release of neuronal histamine in the hypothalamus of rats measured by microdialysis. Naunyn-Schmiedburg's Arch. Pharmacol. 1991, 343, 190-195.
6. 3 receptors in the inhibitory effect of histamine on serotonin release in the rat brain cortex. Naunyn-Schmiedburg's Arch. Pharmacol. 1990, 342, 513-519.
7. 3 receptor subtypes. Br. J. Pharmacol. 1992, 107, 919-923.
8. 3 receptors. Naunyn-Schmiedburg's Arch. Pharmacol. 1992, 346, 46-50.
9. 3 receptors. J. Neural. Transm. Gen. Sect. 1993, 93, 1-10.
10. 3 receptors controlling nonadrenergic noncholinergic contractions of the guinea pig isolated ileum. Br. J. Pharmacol. 1992, 105, 667-674.
11. Prinz, C.; Kajimura, M.; Scott, D. R.; Mercier, F.; Helander, H.; Sachs, G. Histamine secretion from rat enterochromaffin. Gastroenterology 1998, 105, 449-461.
12. 3-receptors on cholinergic nerves in human airways. Eur. J. Pharmacol. 1989, 163, 383-386.
13. 3-receptor in the human heart. Circ. Res. 1995, 77, 206-210.
14. 3 receptor on sleep and wakefulness. Eur. J. Pharmacol. 1991, 205, 283-287.
15. 3 receptor ligands in the cat. Brain Res. 1990, 523, 325-330.
16. 3 receptor antagonist, on electrically induced convulsions in mice. Eur. J. Pharmacol. 1993, 234, 129-133
17. 3 receptor antagonist: in vitro and in vivo studies. J. Pharmacol. Exp. Ther. 1995, 275, 598-604.
18. 3 receptor. In Progress in Drug Research; Jucker, E., Eds.; Birkhauser Verlag: Basel, Switzerland, 1995; Vol. 45, pp 107-165.
19. 3 receptor antagonists. Drugs Future 1996, 21, 507-520.
20. 3 Receptor as a Target for New Drugs; Leurs, R., Timmerman, H., Eds.; Elsevier: Amsterdam, 1998; Vol. 30, pp 197-222.
21. 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.
22. 3 receptor. Eur. J. Med. Chem. 1992, 27, 511-517.
23. 3-antagonist from the marine sponge Verongula gigantea. J. Nat. Prod. 1994, 57, 175-177.
24. 3 receptor antagonists derived from the marine natural product verongamine. Bioorg. Med. Chem. Lett. 1998, 8, 1133-1138.
25. (a) Topliss, J. G. Utilization of operational schemes for analogue synthesis in drug design. J. Med. Chem. 1972, 15, 1006-1011.
26. (b) Topliss, J. G. A manual method for applying the Hanch Approach to Drug Design. J. Med. Chem. 1977, 20, 463-469.
27. Burger, A.; Bernabe, M.; Collins, P. W. 2-(4-Imidazolyl)cyclopropylamine. J. Med. Chem. 1970, 13, 33-55.
28. The enantiomers (1R,2R)trans-butyl 2-(1-(triphenylmethyl)-1H-imidazol-4-yl)cyclopropanecarboxylate and (1S,2S)-trans-butyl 2-(1-(triphenylmethyl)-1H-imidazol-4-yl)cyclopropanecarboxy-late could be separated on a multigram scale using chiral column technology. Using a Chiralcel OD column, Regis Technologies serial #0112201, and an eluent of 90:10 hexanes:isopropyl alcohol, flow rate 1 mL/min, the (1R,2R) enantiomer had a retention time of 5.787 min, whereas its (1S,2S) analogue had a retention time of 7.815 min.
29. 3 receptor agents. Bioorg. Med. Chem. Lett. 1997, 7, 3017-3022.
30. 3 receptor antagonists derived from Verongamine. Abstracts of Papers; Medicinal Chemistry Gordon Conference, Colby Sawyer College, New London, NH, 1996.
31. 3 receptor antagonists derived from Verongamine. Presented at the 11th Camerino-Noordwijkerhout Symposium on Perspectives in Receptor Research, Noordwijkerhout, The Netherlands, 1997.
32. 3 receptor. J. Med. Chem. 1996, 39, 1220-1226.
33. 3 receptor ligands. J. Pharmacol. Exp. Ther. 1999, in press.
34. 3 receptor antagonists. Eur. J. Pharmacol. 1998, 351, 307-311.