New and efficient synthesis of 2-alkoxyapomorphines

Letters in Organic Chemistry

Volumn 4, Issue 1, 2007, Pages 32-34

  Berényi, Sándor ^a   Csutorás, Csaba ^b   Sipos, Attila ^a   Gyulai, Zsuzsanna ^a  

^a UNIVERSITY OF DEBRECEN   (Hungary)

^b ESZTERHÁZY KÁROLY UNIVERSITY   (Hungary)

Author keywords

2 alkoxyapomorphines; Acid catalyzed rearrangement; Dopamine receptor binding affinity; O demethylation; Oripavine

Indexed keywords

EID: 33947187197     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017807780037397     Document Type: Article

References (19)

1. Apomorphine in the treatment of Erectile Dysfunction, see for example: Heaton, J. P. W. Int. J. Impot. Res., 2001, 13(Suppl 3) S35;
2. Padma-Nathan, H.; Auerbach, S.; Lewis, R. J. Urol., 2001, 165(Suppl), 224;
3. Martinez, R.; Puigvert, A.; Pomerol, J. M.; Rodriguez-Villalba, R. J. Urol., 2003, 170, 2352;
4. Perimenis, P.; Gyftopoulos, K.; Giannitsas, K.; Markou, S. A.; Tsota, I.; Chrysanthopoulou, A.; Athanasopoulos, A.; Barbalias, G. Int. J. Impotence Res., 2004, 16, 2.
5. Apomorphine in the treatment of Parkinson's Disease, see for example: Schwab, R. S.; Amador, L. V.; Lettvin, J. Y. Trans. Am. Neurol. Assoc., 1951, 76, 251;
6. Muguet, D.; Cotzias, G. C.; Papavasiliou, P. S.; Tolosa, E. S.; Mendez, J. S.; Bell-Midura, M. N. Engl. J. Med., 1976, 294, 567;
7. Broussolle, E.; Chazot, G. Biomed. Pharmacother., 1995, 49, 197;
8. Sit, S. Y. Curr. Pharm. Des., 2000, 6, 1211;
9. Poewe, W.; Wenning, G. K. Mov. Disorders, 2000, 15, 789.
10. Structure-activity relationship for dopamine receptors, see for example: Ramsby, S.; Neumeyer, J. L.; Grigoriadis, D.; Seeman, P. J. Med. Chem., 1989, 32, 1198;
11. Csutorás, Cs.; Zhang, A.; Zhang, K.; Kula, N. S.; Baldessarini, R. J.; Neumeyer, J. L. Bioorg. Med. Chem., 2004, 12, 3553;
12. Tóth, M.; Berényi, S.; Csutorás, Cs.; Kula, N. S.; Zhang, K.; Baldessarini, R. J.; Neumeyer, J. L. Bioorg. Med. Chem., 2006, 14, 1918;
13. Zhang A.; Csutorás Cs.; Zong R.; Neumeyer J. L. Org. Lett., 2005, 15, 3239.
14. Gao, Y.; Baldessarini, R. J.; Kula, N. S.; Neumeyer, J. L. J. Med. Chem., 1990, 33, 1800.
15. Berényi, S.; Czirják, M.; Makleit, S. J. Chem. Soc. Perkin Trans. I, 1993, 2137
16. Csutorás, Cs.; Berényi, S.; Makleit, S. Synth. Commun., 1996, 26, 2251
17. Coop, A.; Janetka, W. J.; Lewis, J. W.; Rice, K. C. J. Org, Chem., 1998, 63, 4392; L-Selectride (1 M of lithium-tri-secbutylborohydride in THF) was purchased from Aldrich and used undiluted.
18. Elemental analyses were found to be satisfactory for all new compounds.
19. Neumeyer, J. L.; Arana, G. W.; Vishnu, J. R.; Kula, N. S.; Baldessarini, R. J. J. Med. Chem., 1982, 25, 990.