First enantioselective syntheses of the dopamine D1 and D2 receptor modulators, (+)-and (-)-govadine

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 4, 2012, Pages 1557-1559

  Zhai, Huimin ^a   Miller, James ^b   Sammis, Glenn ^a  

^a UNIVERSITY OF BRITISH COLUMBIA   (Canada)

^b Panora Pharmaceuticals Inc   (Canada)

Author keywords

Enantioselective; Govadine; Schizophrenia; Synthesis; Tetrahydroprotoberberine

Indexed keywords

BERBINE DERIVATIVE; DOPAMINE 1 RECEPTOR; DOPAMINE 2 RECEPTOR; GOVADINE; HOMOVANILLIC ACID; NEUROLEPTIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; CRYSTALLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; ENANTIOSELECTIVITY; IN VITRO STUDY; NEGATIVE SYNDROME; POSITIVE SYNDROME;

EID: 84862822299     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.01.005     Document Type: Article

References (33)

1. For a review, see: Freedman, R. N. Engl. J. Med. 2003, 349, 1738.
2. (a) Carlsson, A.; Carlsson, M. L. Dialogues Clin. Neurosci. 2006, 8, 137
3. (b) van Os, J.; Kapur, S. Lancet 2009, 374, 635.
4. (a) Weinberger, D. R.; Egan, M. F.; Bertolino, A.; Callicott, J. H.; Mattay, V. S.; Lipska, B. K.; Berman, K. F.; Goldberg, T. E. Biol. Psychiatry 2001, 50, 825
5. (b) Goldman-Rakic, P. S.; Castner, S. A.; Svensson, T. H.; Siever, L. J.; Williams, G. V. Psychopharmacology 2004, 174, 3.
6. Hsu, B.; Kin, K. C. Arch. Int. Pharmacodyn. 1962, 89, 318.
7. Mo, J.; Guo, Y.; Yang, Y.-S.; Shen, J.-S.; Jin, G.-Z.; Zhen, X. Curr. Med. Chem. 2007, 14, 2996.
8. (a) Jin, G. -Z.; Huang, K.; Sun, B. -C. Neurochem. Int 1992, 20, 175S
9. (b) Jin, G. -Z.; Sun, B. -C. Adv. Exp. Med. Biol. 1995, 363, 27
10. (c) Jin, G. -Z.; Zhu, Z. -T.; Fu, T. Trends Pharmacol. Sci. 2002, 23, 4.
11. (a) Mehra, K.; Garg, H. S.; Bhakuni, D. S.; Khanna, N. M. Indian J. Chem., Sect B 1976, 14B, 216
12. (b) Mehra, K.; Garg, H. S.; Bhakuni, D. S.; Khanna, N. M. Indian J. Chem., Sect B 1976, 14B, 844.
13. Lapish, C. C.; Belardetti, F.; Ashby, D. M.; Ahn, S.; Butts, K. A.; So, K.; Macrae, C. M.; Hynd, J. J.; Miller, J. J.; Phillips, A. G. Int. J. Neuropsychop. in press. Doi: 10.1017/S1461145711001581.
14. (a) Kametani, T.; Satoh, M. J. Pharm. Soc. Jpn 1967, 179
15. (b) Chiang, H.-C.; Brochmann-Hanssen, E. R. J. Org. Chem 1977, 42, 3190
16. (c) Chiang, H.-C.; Cheng, Y.-C.; Liu, J.-C. Taiwan Yaoxue Zazhi 1978, 54, 30
17. (d) Kametani, T.; Ihara, M. J. Chem. Soc., Perkin Trans. 1 1980, 629
18. (e) Yongzhou, H. Chinese J. Med. Chem 1998, 8, 190
19. Bischler, A.; Napieralski, B. Ber. 1893, 26, 1903.
20. Khorna, N.; Markmee, S.; Ingkaninan, K.; Ruchirwat, S.; Kitbunnada, R. J.; Pullagurla, M. R. Med. Chem. Res. 2009, 18, 231.
21. Yang, Y. -S.; Ding, Y.; Sun, P. -H.; Mo, J.; Jin, G. -Z.; , R. -Y. Faming Zhuanli Shenqing Gongkai Shuomingshu 2007. CN 1900075 A.
22. Iwasa, K.; Cui, W.; Takahashi, T.; Nishiyama, Y.; Kamigauchi, M.; Koyama, J.; Takeuchi, A.; Moriyasu, M.; Takeda, K. J. Nat. Prod. 2010, 73, 115.
23. Uematsu, N.; Fujii, A.; Hashiguchi, S.; Ikariya, T.; Noyori, R. J. Chem. Soc. 1996, 118, 4916.
24. (a) Bedejs, E.; Trapencieris, P.; Suna, E. J. Org. Chem. 1999, 64, 6724
25. (b) Tietze, L. F.; Rackelmann, N.; Sekar, G. Angew. Chem., Int. Ed. 2003, 42, 4254
26. (c) Mujahidin, D.; Doye, S. Eur. J. Org. Chem 2005, 2689
27. (d) Werner, F.; Blank, N.; Opatz, T. Eur. J. Org. Chem 2007, 3911.
28. Cheng, J. -J.; Yang, Y. -S. J. Org. Chem. 2009, 74, 9225.
29. Pyo, M. K.; Lee, D. H.; Kim, D. H.; Lee, J. H.; Moon, J. C.; Chang, K. C.; Choi, H. S. Y. Bioorg. Med. Chem. Lett. 2008, 18, 4110.
30. For examples, see: (a) Parvulescu, A. N.; De Vos, D. E.; Jacobs, P. A. Chem. Commun 2005, 42, 5307
31. (b) Parvulescu, A. N.; Jacobs, P. A.; De Vos, D. E. Chem. Eur. J 2007, 13, 2034
32. (c) Parvulescu, A. N.; Van der Eycken, E.; Jacobs, P. A.; De Vos, D. E. J. Catal. 2008, 255, 206
33. (d) Ref. 17.