Synthesis of 1-arylpiperazyl-2-phenylcyclopropanes designed as antidopaminergic agents: Cyclopropane-based conformationally restricted analogs of haloperidol

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 19, 2008, Pages 8875-8881

  Yamaguchi, Kazuya ^a   Kazuta, Yuji ^a   Hirano, Kazufumi ^b   Yamada, Shizuo ^b   Matsuda, Akira ^a   Shuto, Satoshi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b UNIVERSITY OF SHIZUOKA   (Japan)

Author keywords

Conformational restriction; Cyclopropane; Dopamine receptor

Indexed keywords

1 ARYLPIPERAZYL 2 PHENYLCYCLOPROPANE DERIVATIVE; CYCLOPROPANE DERIVATIVE; DOPAMINE 2 RECEPTOR; DOPAMINE 4 RECEPTOR; DOPAMINE RECEPTOR BLOCKING AGENT; HALOPERIDOL; IMINE; TERT BUTANESULFINYL IMINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CONFORMATIONAL TRANSITION; CONTROLLED STUDY; DOPAMINE RECEPTOR BLOCKING; DOPAMINE RELEASE; DRUG CONFORMATION; DRUG DESIGN; DRUG EFFICACY; DRUG FORMULATION; DRUG SELECTIVITY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN TISSUE; MALE; MOUSE; NONHUMAN;

BUTANES; CYCLOPROPANES; DOPAMINE ANTAGONISTS; DRUG DESIGN; HALOPERIDOL; IMINES; MOLECULAR CONFORMATION; PIPERAZINES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 52949115643     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.08.061     Document Type: Article

References (48)

1. Silverman R.B. The Organic Chemistry of Drug Design and Drug Action (2004), Academic Press, San Diego
2. In: Kozikowski A. (Ed). Drug Design for Neuroscience (1993), Raven Press, New York
3. In: Wermuth C.G. (Ed). The Practice of Medicinal Chemistry (1996), Academic Press, San Diego
4. Ohmori Y., Yamashita A., Tsujita R., Yamamoto T., Taniuchi K., Matsuda A., and Shuto S. J. Med. Chem. 46 (2003) 5326 and references therein
5. de Meijere A. Angew. Chem., Int. Ed. Engl. 18 (1979) 809
6. Wong H.N.C., Hon M.-Y., Tse C.-W., Yip Y.-C., Tanko J., and Hudlicky T. Chem. Rev. 89 (1989) 165
7. Stammer C.H. Tetrahedron 46 (1990) 2231
8. Small Ring Compounds in Organic Synthesis VI. Topic in Current Chemistry 207; de Meijere, A., Ed.; Springer: Berlin, 1999.
9. For examples see:. Armstrong D.P., and Cannon J.G. J. Med. Chem. 13 (1970) 1037
10. Stammer S.H. Tetrahedron 46 (1990) 2231
11. Shimamoto K., and Ofune Y. J. Med. Chem. 39 (1996) 407
12. Sekiyama T., Hatsuya S., Tanaka Y., Uchiyama M., Ono N., Iwayama S., Oikawa M., Suzuki K., Okunishi M., and Tsuji T. J. Med. Chem. 41 (1998) 1284
13. Martin S.F., Dwyer M.P., Hartmann B., and Knight K.S. J. Org. Chem. 65 (2000) 1305
14. Kazuta Y., Hirano K., Natsume K., Yamada S., Kimura R., Matsumoto S., Furuichi K., Matsuda A., and Shuto S. J. Med. Chem. 46 (2003) 1980
15. Watanabe M., Kazuta Y., Hayashi H., Yamada S., Matsuda A., and Shuto S. J. Med. Chem. 49 (2006) 5587
16. Ono S., Shuto S., and Matsuda A. Tetrahedron Lett. 37 (1996) 221
17. Shuto S., Ono S., Hase Y., Kamiyama N., and Matsuda A. Tetrahedron Lett. 37 (1996) 641
18. Shuto S., Ono S., Hase Y., Kamiyama N., Takada H., Yamashita K., and Matsuda A. J. Org. Chem. 61 (1996) 915
19. Shuto S., Ono S., Hase Y., Ueno Y., Noguchi T., Yoshii K., and Matsuda A. J. Med. Chem. 39 (1996) 4844
20. Shuto S., Ono S., Imoto H., Yoshii K., and Matsuda A. J. Med. Chem. 41 (1998) 3507
21. Noguchi T., Ishii K., Imoto H., Otubo Y., Shuto S., Ono S., Matsuda A., and Yoshii K. Synapse 31 (1999) 87
22. Uchino S., Watanabe W., Nakamura T., Shuto S., Kazuta Y., Matsuda A., Nakajima-Iijima S., Kohsaka S., Kudo Y., and Mishina M. FEBS Lett. 69 (2001) 2007
23. Kazuta Y., Tsujita R., Ogawa K., Hokonohara T., Yamashita K., Morino K., Matsuda A., and Shuto S. Bioorg. Med. Chem. 10 (2002) 1777
24. Kazuta Y., Tsujita R., Uchino S., Kamiyama N., Mochizuki D., Yamashita K., Ohmori Y., Yamashita A., Yamamoto T., Uchino S., Kohsaka S., Matsuda A., and Shuto S. J. Chem. Soc., Perkin Trans. 1 (2002) 1199
25. Ono S., Ogawa K., Yamashita K., Yamamoto T., Kazuta Y., Matsuda A., and Shuto S. Chem. Pharm. Bull. 50 (2002) 966
26. Kazuta Y., Tsujita R., Yamashita K., Uchino S., Kohsaka S., Matsuda A., and Shuto S. Bioorg. Med. Chem. 10 (2002) 3829
27. Shuto S., Takada H., Mochizuki D., Tsujita R., Hase Y., Ono S., Shibuya N., and Matsuda A. J. Med. Chem. 38 (1995) 2964
28. In: Neve K.A., and Neve R.L. (Eds). The Dopamine Receptors (1997), Humana Press, Totowa
29. Sibley D.R., and Monsma Jr. F.J. Trends Pharmacol. Sci. 13 (1992) 61
30. Zhang X., Hodgetts K., Rachwal S., Zhao H., Wasley J.W.F., Craven K., Brodbeck R., Kieltyka A., Hoffman D., Bacolod M.D., Girard B., Tran J., and Thurkauf A. J. Med. Chem. 43 (2000) 3923
31. Singh V.K., DattaGupta A., and Sekar G. Synthesis (1997) 137
32. Doyle M.P., and Protopopova M.N. Tetrahedron 54 (1998) 7919
33. Cossy J., Blanchard N., and Meyer C. Synthesis (1999) 1063
34. Lebel H., Marcoux J.-F., Molinaro C., and Charette A.B. Chem. Rev. 103 (2003) 977
35. Muller P., Allenbach Y.F., Chappellet S., and Ghanem A. Synthesis (2006) 1689
36. Kazuta Y., Matsuda A., and Shuto S. J. Org. Chem. 67 (2002) 1669
37. Kazuta Y., Abe H., Yamamoto T., Matsuda A., and Shuto S. J. Org. Chem. 68 (2003) 3511
38. Kazuta Y., Abe H., Yamamoto T., Matsuda A., and Shuto S. Tetrahedron 60 (2004) 6689
39. Kazuta Y., Abe H., Matsuda A., and Shuto S. J. Org. Chem. 69 (2004) 9143 and references therein
40. The cis-analog 3 and its enantiomer ent-3 were synthesized using a stereoselective radical decarboxylation constructing the cis-cyclopropane structure as the key step:. Yamaguchi K., Kazuta Y., Matsuda A., and Shuto S. J. Org. Chem. 68 (2003) 9255
41. Kochi T., Tang T.P., and Ellman J.A. J. Am. Chem. Soc. 124 (2002) 6518
42. McMahon J.P., and Ellman J.A. Org. Lett. 6 (2004) 1645
43. Yoshida K., Yamaguchi K., Sone T., Unno Y., Asai A., Yokosawa H., Matsuda A., Arisawa M., and Shuto S. Org. Lett. 10 (2008) 3571
44. Ohtani I., Kusumi T., Kashman Y., and Kakisawa H. J. Am. Chem. Soc. 113 (1991) 4092
45. Kusumi T., Fukushima T., Ohtani I., and Kakisawa H. Tetrahedron Lett. 32 (1991) 2939
46. Yamada S., Ashizawa N., Ushijima H., Nakayama K., Hayashi E., and Honda K. J. Pharmacol. Exp. Ther. 242 (1987) 326
47. Yamada S., Yamamura H.I., and Roeske W.R. J. Pharmacol. Exp. Ther. 215 (1980) 176
48. Rosenthal H.E. Anal. Biochem. 20 (1967) 525