Enantioselective synthesis and absolute configuration of (-)-1-(benzofuran-2-yl)-2-propylaminopentane, ((-)-BPAP), a highly potent and selective catecholaminergic activity enhancer

Bioorganic and Medicinal Chemistry

Volumn 9, Issue 5, 2001, Pages 1213-1219

  Oka, Takahiro ^a   Yasusa, Takuya ^a   Ando, Takashi ^a   Watanabe, Mayumi ^a   Yoneda, Fumio ^a   Ishida, Toshimasa ^b   Knoll, Joseph ^c  

^a Fujimoto Pharmaceutical Corporation   (Japan)

^b OSAKA MEDICAL COLLEGE   (Japan)

^c SEMMELWEIS UNIVERSITY OF MEDICINE   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

1 (BENZOFURAN 2 YL) 2 PROPYLAMINOPENTANE; BENZOFURAN DERIVATIVE; N METHOXY N METHYLNORVALIAMIDE; N TOSYL 2 PROPYLAZIRIZINE; NORVALINE; UNCLASSIFIED DRUG;

ARTICLE; CATECHOLAMINERGIC SYSTEM; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; ENANTIOMER; REACTION ANALYSIS; X RAY CRYSTALLOGRAPHY;

AZIRINES; BENZOFURANS; CATECHOLAMINES; CRYSTALLOGRAPHY, X-RAY; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 0035008575     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(00)00341-2     Document Type: Article

References (26)

1. Knoll J., Miklya I. Life Sci. 56:1995;611.
2. Knoll J. Pharmacol. Toxicol. 75:1994;65.
3. Knoll J. Biomed. & Pharmacother. 49:1995;187.
4. Knoll J. Exp. Gerontol. 32:1997;539.
5. Knoll J. Neurobiology. 8:2000;179.
6. Knoll J., Magyar K. Adv. Bioch. Psychopharmacol. 5:1972;393.
7. Knoll J., Knoll B., Török Z., Timár J., Yasar S. Arch. int. Pharmacodyn. Thér. 316:1992;5.
8. Knoll J. Mech. Ageing & Dev. 46:1988;237.
9. Tatton W.G., Grenwood C.E. J. Neurosci. Res. 30:1991;666.
10. Terud J.W., Langston J.W. Science. 245:1989;519.
11. New. Engl. J. Med. 321:1989;1364.
12. Sano M., Ernesto C., Thomas R.G., Klauber M.R., Schafer K., Grundman M., Woodbury P., Growdon J., Cotman C.W., Pfeiffer E., Schneider L.S., Thal L. J. New Engl. J. Med. 336:1997;1216.
13. Knoll J. Pharmacol. Toxicol. 82:1998;57.
14. Knoll J., Yoneda F., Knoll B., Ohde H., Miklya I. British J. Pharm. 128:1999;1723.
15. Yoneda, F.; Moto, T.; Sakae, M.; Ohde, H.; Knoll, B.; Miklya, I.; Knoll, J. Bioorg. Med. Chem. 2001, 9, in press.
16. Gschwend H.W., Rodriguez H.R. Org. React. (N.Y.). 26:1972;1.
17. Oppolzer W., Flaskamp E. Hel. Chim. Acta. 22:1977;204.
18. Farmer J.J., Attygalle A.B., Smedley S.R., Eisner T., Meinwald J. Tetrahedron Lett. 38:1997;2787.
19. Edwards P.D., Wolanin D.J., Andisk D.W., Davis M.W. J. Med. Chem. 38:1995;76.
20. Sun G., Slavica M., Uretsky N.J., Wallace L.J., Shams G., Weinstein D.M., Miller J.C., Millar D.D. J. Med. Chem. 41:1998;1034.
21. Conditions for analytical chromatography of 1: column, CHIRALPAK AD-RH (0.46 cm×1.5 cm); eluent, 20 mM phosphate buffer (pH 8.0):acetonitrile=3:2; flow rate, 1.0 mL/min; detection, UV 249 nm; retention times 35 (R) and 39 min (S). The (R)-1·HCl obtained by two methods was in high optical purity (>98% ee).
22. Dina G.D., Otto M.J., Treasurywala A.M., McKinlay M.A., Oglesby R.C., Maliski E.G., Rossmann M.G., Smith T.J. J. Med. Chem. 31:1988;540.
23. Davis F.A., Zhou P., Liang C.-H, Reddy R.E. Tetrahedron: Asymmetry. 6:1995;1511.
24. Izumiya N., Yamashita T. J. Biochem. 46:1959;19.
25. Sheldrick, G. M., SHELXS 97. Programs for the Solution of Crystral Structure, University of Göttingen, Germany, 1997.
26. International Tables for X-ray Crystallography, Vol. C, Kluwer Academic Publishers, 1992.