1-Oxo-5-hydroxytryptamine: A surprisingly potent agonist of the 5-HT 3 (serotonin) receptor

Organic Letters

Volumn 9, Issue 17, 2007, Pages 3205-3207

  Kedrowski, Sean M A ^a   Bower, Kiowa S ^a   Dougherty, Dennis A ^a  

^a California Institute of Technology

Author keywords

[No Author keywords available]

Indexed keywords

1 OXO 5 HYDROXYTRYPTAMINE; 1-OXO-5-HYDROXYTRYPTAMINE; BENZOFURAN; BENZOFURAN DERIVATIVE; DRUG DERIVATIVE; SEROTONIN; SEROTONIN AGONIST; SEROTONIN RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG EFFECT; HUMAN; SYNTHESIS;

BENZOFURANS; HUMANS; RECEPTORS, SEROTONIN; SEROTONIN; SEROTONIN AGONISTS;

EID: 34548181843     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol071083s     Document Type: Article

References (29)

1. Rapport, M. M.; Green, A. A.; Page, I. H. J, Biol. Chem. 1948, 176, 1243-1251.
2. (a) Bloom, F. E.; Kupfer, D. J. Psychopharmacology: the fourth generation of progress, 4th ed., official publication of the American College of Neuropsychopharmacology; Raven Press: New York, 1995.
3. (b) Davis, K. L. Neuropsychopharmacology: the fifth generation of progress, official publication of the American College of Neuropsychopharmacology; Lippincott/Williams & Wilkins: Philadelphia, PA, 2002.
4. Paterson, D. S.; Trachtenberg, F. L.; Thompson, E. G.; Belliveau, R. A.; Beggs, A. H.; Darnall, R.; Chadwick, A. E.; Kraus, H. F.; Kinney, H. C. JAMA, J. Am. Med. Assoc. 2006, 296, 2124-2132.
5. For reviews of 5-HT receptors, see ref 2 and: (a) Meltzer, H. Y.; Li, Z.; Kaneda, Y. Prog. Neuro-Psychopharmacol. Biol. Psychiatry 2003, 27, 1159-1172.
6. (b) Barnes, N. M.; Sharp, T. Neuropharmacology 1999, 38, 1083.
7. (c) Pucadyil, T. J.; Kalipatnapu, S.; Chattopadhyay, A. Cell Mol. Neurobiol. 2005, 25, 553.
8. (d) Leopoldo, A. Curr. Med. Chem. 2004, 11, 629.
9. (e) Bishop, M. J.; Nilsson, B. M. Expert Opin. Ther. Pat. 2003, 13, 1691.
10. (f) Poissonet, G.; Parmentier, J. G.; Boutin, J. A. Expert Opin. Ther. Pat. 2004, 4, 325.
11. (g) Thomas, D. R. Pharmacol. Therapeut. 2006, 111, 707.
12. (a) Thompson, A. J.; Lummis, S. C. R. Curr. Pharm. Des. 2006, 12, 3615.
13. (b) Reeves, D. C.; Lummis, S. C. R. Mol. Memb. Biol. 2002, 19, 11.
14. (c) Maricq, A. V.; Peterson, A. S.; Brake, A. J.; Myers, R. M.; Julius, D. Science 1991, 254, 432-437.
15. (d) Greenshaw, A. J. Trends Pharmacol. Sci. 1993, 14, 265-270.
16. (e) Gyermek, L. J. Clin. Pharmacol. 1995, 35, 845-855.
17. (a) Beene, D. L.; Price, K. L.; Lester, H. A.; Dougherty, D. A.; Lummis, S. C. R. J. Neurosci. 2004, 24, 9097-9104.
18. (b) Bower, K. S.; Price, K. L.; Sturdee, L. F.; Dougherty, D. A.; Lummis, S. Submitted for publication.
19. Hallmann, G.; Hagele, K. Leibigs. Ann. Chem. 1963, 662, 147.
20. There is one published pharmacological experiment on 1-OT (ref 9): the drug was assayed by measuring the rate of muscular contraction following drug application to surgically removed rat fundus strips.
21. Pinder, R. M.; Green, D. M.; Thompson, P. B. J. Med. Chem. 1971, 14, 626-628.
22. (a) Domschke, G. J. Prankt. Chem. 1966, 32, 144.
23. (b) Yadav, J. S.; Reddy, B. V. S.; Kondaji, G. Synthesis 2003, 1100-1104.
24. Zhou, G.; Corey, E. J. J. Am. Chem. Soc. 2005, 127, 11958-11959.
25. (a) Nomura, Y.; Ogawa, K.; Takeuchi, Y.; Tomoda, S. Chem. Lett. 1977, 693-696.
26. (b) Kraus, G. A.; Neuenschwander, K. J. Org. Chem. 1981, 46, 4791-4792.
27. (c) Marais, W.; Holzapfel, C. W. Synth. Commun. 1998, 28, 3681-3691.
28. It is further worth noting that when pure 6 was subjected to the isomerization conditions in the presence of quinone 3, no product 8 could be observed.
29. Kan, T.; Fukuyama, T. Chem. Commun. 2004, 353-359.