Benzoxazole derivatives as novel 5-HT3 receptor partial agonists in the gut

Journal of Medicinal Chemistry

Volumn 41, Issue 16, 1998, Pages 3015-3021

  Sato, Yasuo ^a,b   Yamada, Megumi ^a   Yoshida, Satoshi ^a   Soneda, Tomoko ^a   Ishikawa, Midori ^a   Nizato, Tetsutaro ^a   Suzuki, Kokichi ^a   Konno, Fukio ^a  

^a Cent Res Lab   (Japan)

^b YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 CHLORO 7 METHYL 2 (4 METHYL 1 HOMOPIPERAZINYL)BENZOXAZOLE; BENZOXAZOLE DERIVATIVE; GRANISETRON; PARTIAL AGONIST; SEROTONIN 3 AGONIST; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CONTROLLED STUDY; DESCENDING COLON; DIARRHEA; DRUG ACTIVITY; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; GUINEA PIG; INTRAVENOUS DRUG ADMINISTRATION; IRRITABLE COLON; MALE; MOUSE; NONHUMAN; RAT; RECEPTOR AFFINITY;

ANIMALS; BENZOXAZOLES; CEREBRAL CORTEX; COLON; DIARRHEA; GASTROINTESTINAL TRANSIT; GUINEA PIGS; ILEUM; INTESTINES; MALE; MICE; MUSCLE CONTRACTION; MUSCLE, SMOOTH; PIPERAZINES; RATS; RATS, WISTAR; RECEPTORS, SEROTONIN; RECEPTORS, SEROTONIN, 5-HT3; REFLEX; SEROTONIN AGONISTS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0032581493     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9801004     Document Type: Article

References (38)

1. 3 Receptors. Med. Chem. Res. Rev. 1990, 10, 441-475 and references therein.
2. Gerhardt, C. C.; Heerikhuizen, H. Functional Characteristics of Heterologously Expressed 5-HT Receptors. Eur. J. Pharmacol. 1997, 334, 1-23.
3. Boess, F. G.; Martin, I. L. Molecular Biology of 5-HT Receptors. Neuropharmacology 1994, 33, 275-317.
4. 3 receptors: Pharmacologie and Therapeutic Aspects. J. Clin. Pharmacol. 1995, 35, 845-855.
5. Hoyer, D.; Clarke, D. E.; Fozard, J. R. International Union Pharmacology Classification of Receptors for 5-Hydroxytryptamine (Serotonin). Pharmacol. Rev. 1994, 46, 157-203.
6. 3 Receptor Antagonists. Exp. Opin. Ther. Pat. 1994, 4, 669-680.
7. 3 Receptor Antagonists, an Overview of Their Present Status and Future Potential in Cancer Therapy-Induced Emesis. Drugs 1991, 42, 551-568.
8. Sanger, G. J.; Nelson, G. R. Selective and Functional 5-Hydroxytriptamine Receptor Antagonism by BRL43694. Eur. J. Pharmacol. 1989, 159, 113-124.
9. 3 Receptors. Br. J. Pharmacol. 1988, 94, 387-412.
10. Richardson, B. P.; Engel, G.; Donatsch, P.; Stadler, P. A. Identification of Serotonin m-Receptor Subtypes and Their Specific Blockade by a New Class of Drugs. Nature 1985, 316, 126-131.
11. 3 Receptor Antagonists. Drugs 1997, 53, 20-39.
12. 3 Receptor Antagonists: a Critical Update on Therapeutic Potential. Trends Pharmacol. Sci. 1993, 14, 265-270.
13. 3 Receptor Ligand: Agonistic Activities on Gastroenteric Motility. Biol. Pharm. Bull. 1997, 20, 752-755.
14. Talley, N. J. 5-Hydroxytriptamine Agonists and Antagonists in the Modulation of Gastrointestinal Motility and Sensation: Clinical Implications. Aliment. Pharmacol. Ther. 1992, 6, 273-289.
15. Steadman, C. J.; Talley, N. J.; Phillips, S. F.; Zinsmeister, A. R. Selective 5-Hydroxytryptamine Type 3 Receptor Antagonism with Ondancetron as Treatment for Diarrhoea-predominant Irritable Bowel Syndrome - A Pilot Study. Mayo Clin. Proc. 1992, 67, 732-738.
16. Sanger, G. J. 5-Hydroxytriptamine and Functional Bowel Disorders. Neurogastroenterol. Mot. 1996, 8, 319-331.
17. Glennon, R. A.; Dukat, M. Serotonin. Update 1992. Curr. Drugs 1992, 1-45.
18. 3 Receptor Agonist Action in the Gut. Chem. Pharm. Bull. 1998, 46, 445-451.
19. Dunner, J. Ueber das Produkt der Einwirkung von Schwefelkohleustoff auf das Orthoamidophenol. Ber. 1876, 9, 465-466.
20. Orjales, A.; Bordell, M.; Rubio, V. Synthesis and Structure -activity Relationship of New Piperidinyl and Piperazinyl Derivatives as Antiallergics. J. Heterocycl. Chem. 1995, 32, 707-718.
21. 3 Receptors in Rat Brain Using Radiorigand Binding. Nature 1987, 330, 746-748.
22. 4 Agonist Properties. J. Med. Chem. 1994, 37, 1320-1325.
23. Fozard, J. R.; Host, M. Selective Inhibition of the Bezold-Jarisch Effect of 5-HT in the Rat by Antagonists at Neuronal 5-HT Receptors. Br. J. Pharmacol. 1982, 77, 520P.
24. 3H]RS-42358-197: Evidence for Receptor Heterogeneity. J. Neurochem. 1993, 5, 1927-1932.
25. 3 Receptors of the Rat, Mouce and Guinea-pig Superior Cervical Ganglion May be Different. Br. J. Pharmacol. 1991, 102, 615-620.
26. 3 Receptors in Three Isolated Preparations Derived from Guinea-pig Tissues. Br. J. Pharmacol. 1990, 101, 591-598.
27. 3 Receptor Channel. Annu. Rev. Physiol. 1995, 57, 447-468.
28. 4 Receptor Dual Antagonist. On Colonie Function in vivo. J. Pharmacol. Exp. Ther. 1993, 266, 74-80.
29. 2-Adrenoceptor Agonists upon Colonie Propulsion. Drug Dev. Res. 1986, 9, 241-247.
30. Gibson, G. P. Nitro-Derivatives of o-Cresol. J. Chem. Soc. 1925, 127t1, 42-48.
31. Clewley, R. G.; Cross, G. G.; Fischer, A.; Henderson, G. N. Formation of 4-Halo-4-nitrocyclohexa-2,5-dienones on Nitration of p-Halophenols and p-Halophenyl Acetates. Tetrahedron 1989, 5, 1299-1310.
32. Kiyomine, A.; Ogawa, M.; Tagami, H.; Yoshiwara, T.; Kawase, J.; Tamura, T.; Nishizawa, Y.; Matsunaga, K. JP Patent 6-80542, March 22, 1994.
33. Masilamani, D.; Rogic, M. Sulfuryl Chloride as a Reagent for Selective Chlorination of Symmetrical Ketones and Phenols. J. Org. Chem. 1981, 46, 4486-4489.
34. Bloomfield, C.; Manglik, A. K; Moodie, R. B.; Schofield, K.; Tobin, G. D. Electrophilic Aromatic Substitution. Part 28. The Mechanism of Nitration of Some 4-Substituted Anisoles and Phenols, and of Rearrangement of the Intermediate 4-Nitro-4-substituted-cyclohexa-2,5-dienones. J. Chem. Soc., Perkin Trans. II 1983, 75-82.
35. Kano, F.; Yamane, K.; Yamashita, K.; Hosoe, K.; Kiyoshi, W. JP Patent 64-6279, Jan. 10, 1989.
36. Diepolder, E. Uber Derivate des 1,2-Dimethyl-benzols. II. Ber. 1911, 2498-2503.
37. Cross, G. G.; Fischer, A.; Henderson, G. N.; Smyth, T. A. ipso-Nitration. XXIV. Nitration of 2-Methylphenols. Formation and Rearrangement of 6-Methyl-6-Nitrocyclohexa-2,4-dienones. Can. J. Chem. 1984, 62, 1446-1451.
38. 50) of an Enzymatic Reaction. Biochem. Pharmacol. 1973, 92, 881-894.