Synthesis and 5α-reductase inhibitory activities of benzofuran derivatives with a carbamoyl group

Bioorganic and Medicinal Chemistry Letters

Volumn 8, Issue 6, 1998, Pages 561-566

  Ishibashi, Koki ^a   Nakajima, Katsuyoshi ^a   Sugioka, Yuki ^a   Sugiyama, Mitsuo ^a   Hamada, Takakazu ^a   Horikoshi, Hiroyoshi ^a   Nishi, Takahide ^a  

^a DAIICHI SANKYO CO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOFURAN DERIVATIVE; STEROID 5ALPHA REDUCTASE;

ARTICLE; CYCLIZATION; DRUG ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HUMAN; NONHUMAN; RAT; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

ANIMALS; BENZOFURANS; CARBAMATES; ENZYME INHIBITORS; HUMANS; MODELS, CHEMICAL; MODELS, MOLECULAR; RATS; TESTOSTERONE 5-ALPHA-REDUCTASE;

EID: 0032539793     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(98)00001-8     Document Type: Article

References (19)

1. 1) Siiteri, P. K.; Wilson, J. D. J. Clin. Invest. 1970, 49, 1737.
2. 2) Abell, A. D.; Henderson, B. R. Curr. Med. Chem. 1995, 2, 583.
3. 3) a) Liang, T.; Liao, S. Biochem. J. 1992, 28, 557.
4. b) Hartmann, R. W.; Reichart, M.; Gohring, S. Eur. J. Med. Chem. 1994, 29, 807.
5. c) Kattner, L.; Gohring, S.; Hartmann, R. W. Arch. Pharm. 1995, 328, 239.
6. d) Kumazawa, T.; Takami, H.; Kishibayashi, N.; Ishii, A.; Nagahara, Y.; Hirayama, N.; Obase, H. J. Med. Chem. 1995, 38, 2887.
7. e) Holt, D. A.; Yamashita, D. S.; Koniarian-Beck, A. L.; Luengo, J. I.; Abell, A. D.; Bergsma, D. J.; Brandt, M.; Levy, M. A. J. Med. Chem. 1996, 38, 13.
8. f) Nakai, H.; Terashima, H.; Arai, Y. Ono Pharmaceutical Co., Ltd., EP 0291245 (1988); Chem. Abstr. 1989, 110, 212384t.
9. f) Nakai, H.; Terashima, H.; Arai, Y. Ono Pharmaceutical Co., Ltd., EP 0291245 (1988); Chem. Abstr. 1989, 110, 212384t.
10. g) Okada, S.; Sawada, N.; Kayakiri, N.; Sawada, Y.; Tanaka, H.; Hashimoto, M. Fujisawa Pharmaceutical Co., Ltd., WO 930301-A1 (1992); Chem. Abstr. 1993, 119, 49227u.
11. g) Okada, S.; Sawada, N.; Kayakiri, N.; Sawada, Y.; Tanaka, H.; Hashimoto, M. Fujisawa Pharmaceutical Co., Ltd., WO 930301-A1 (1992); Chem. Abstr. 1993, 119, 49227u.
12. 4) a) Kojima, K.; Kurata, H.; Ishibashi, K.; Hamada, T.; Horikoshi, H. Sankyo Co., Ltd., EP 565271-A2 (1993); Chem. Abstr. 1994, 120, 134929q.
13. 4) a) Kojima, K.; Kurata, H.; Ishibashi, K.; Hamada, T.; Horikoshi, H. Sankyo Co., Ltd., EP 565271-A2 (1993); Chem. Abstr. 1994, 120, 134929q.
14. b) Kurata, H.; Ishibashi, K.; Saito, S.; Hamada, T.; Horikoshi, H.; Furukawa, Y.; Kojima, K. Chem. Pharm. Bull. 1996, 44, 115.
15. 5) Mooradian, A.; Dupont, P. E. J. Heterocyclic Chem. 1967, 4, 441.
16. 6) Kurata, H.; Ishibashi, K.; Kojima, K. Synlett. 1996, 517.
17. 7) Hiroya, K.; Hashimura, K.; Ogasawara, K. Heterocycles 1994, 38, 2463.
18. 3, Z=8, R=0.067, Rw=0.066. Full X-ray crystallographic data will be deposited with the Cambridge Crystallographic Data Centre.
19. 14C] testosterone, 1 mM dithiothreitol and 1mM NADPH. Test sample was added in 5 mM of dimethyl sulfoxide (DMSO) and the control tube received the same volume of DMSO. The reaction was carried out for 15 min at 37°C and then stopped with 2 ml of ethyl acetate containing testosterone, 5α-dihydrotestosterone and androstenedione (10 μg each). The following procedure was the same as that described in the reference 4b.