Synthesis of benzo[c]quinolizin-3-ones: Selective non-steroidal inhibitors of steroid 5α-reductase 1

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 20, 1998, Pages 2871-2876

  Guarna, Antonio ^a   Occhiato, Ernesto G ^a   Scarpi, Dina ^a   Tsai, Ruey ^b   Danza, Giovanna ^a   Comerci, Alessandra ^a   Mancina, Rosa ^a   Serio, Mario ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

^b Serono International SA   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

2,3,5,6 TETRAHYDRO 1H BENZO[C]QUINOLIZIN 3 ONE; AZASTEROID; FINASTERIDE; STEROID 5ALPHA REDUCTASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG CONFORMATION; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME INHIBITION; ENZYME SPECIFICITY; HUMAN; MALE TYPE ALOPECIA; STRUCTURE ACTIVITY RELATION;

ALOPECIA; ENZYME INHIBITORS; HUMANS; INHIBITORY CONCENTRATION 50; ISOENZYMES; MALE; PROSTATE; QUINOLIZINES; TESTOSTERONE 5-ALPHA-REDUCTASE;

EID: 0032552848     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00505-8     Document Type: Article

References (22)

1. 1. For recent reviews on steroid 5α-reductase and its inhibitors see: a) Holt, D. A.; Levy, M. A.; Metcalf, B. W. Adv. Med. Chem. 1993, 2, 1-29;
2. b) Russell, D. W.; Wilson, J. D. Annu. Rev. Biochem. 1994, 63, 25-61;
3. c) Abell, A. D.; Henderson, B. R. Curr. Med. Chem. 1995, 2, 583-97;
4. d) Li, X.; Chen, C.; Singh, S.; Labrie, F. Steroids 1995, 60, 430-41;
5. e) Frye, S.V. Curr. Pharm. Des. 1996, 2, 59-84;
6. f) Kenny, B.; Ballard, S.; Blagg, S.; Fox, D. J. Med. Chem. 1997, 40, 1293-1315.
7. 2. a) Guarna, A.; Poletti, A.; Catrambone, F.; Danza, G.; Marrucci, A.; Serio, M.; Celotti, F.; Martini, L. Bioorg. Med. Chem. Lett. 1996, 6, 1997-2002.
8. b) Guarna, A.; Danza, G.; Bartolucci, G.; Marrucci, A.; Dini, S.; Serio, M. J. Chromatogr., B: Biomed. Appl. 1995, 674, 197-204.
9. 3. Guarna, A.; Marrucci, A.; Danza, G.; Serio, M. Int. Congr. Ser. 1994, 1064, 93-108.
10. 4. Guarna, A.; Belle, C.; Machetti, F.; Occhiato, E. G.; Payne, A. H.; Cassiani, C.; Comerci, A.; Danza, G.; De Bellis, A.; Dini, S.; Marrucci, A.; Serio, M. J. Med. Chem. 1997, 40, 1112-1129.
11. 5. Guarna, A.; Occhiato, E. G.; Machetti, F.; Marrucci, A.; Danza, G.; Serio, M.; Paoli, P. J. Med. Chem. 1997, 40, 3466-3477.
12. 6. Mayer, F.; Van Zutphen, L.; Philips, H. Chem. Ber. 1927, 60, 858-864.
13. 7. Pilli, R. A.; Dias, L.C.; Maldaner, A. O. J. Org. Chem 1995, 60, 717-722.
14. 8. Zaugg, H. E. Synthesis 1984, 181-212 and references therein.
15. 9. Guarna, A.; Occhiato, E. G.; Machetti, F.; Scarpi, D. J. Org. Chem. 1998, 63, 4111-4115.
16. 10. All new compounds gave spectral data and elemental analysis consistent with the assigned structure.
17. 11. Jung, M. E.; McCombs, C. A. Organic Syntheses 1978, 58, 163-167.
18. 12. Leonard, N. J.; Hay, A. S.; Fulmer, R. W.; Gash, V. W. J. Am. Chem. Soc. 1955, 50, 4429-4432.
19. 13. Thigpen, A. E.; Cala, K. M.; Russell, D. W. J. Biol. Chem. 1993, 268, 17404-17412.
20. 14. Abell, A. D.; Erhard, K. F.; Yen, H. K.; Yamashita, D. S.; Brandt, M.; Mohammed, H.; Levy, M. A.; Holt, D. A. Bioorg. Med. Chem. Lett. 1994, 4, 1365-1368.
21. 15. Mook, R. A., Jr.; Lackey, K.; Bennett, C. Tetrahedron Lett. 1995, 36, 3969-3972.
22. 16 Abell, A. D.; Brandt, M.; Levy, M. A.; Holt, D. A. Bioorg. Med Chem. Lett. 1994, 4, 2327-2330.