Synthesis of 4-Aza-3-oxo-androstane-17β-carboxylic Acid, a Key Intermediate for the Preparation of Potent 5α-Reductase Inhibitors

Chinese Pharmaceutical Journal

Volumn 55, Issue 3, 2003, Pages 213-219

  Kan, Wai Ming ^a   Yek, Yung Lee ^b   Wang, Yao Hsien ^c   Chern, Ching Yuh ^c  

^a NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

^b TAINAN SIN LAU HOSPITAL   (Taiwan)

^c NATIONAL CHIAYI UNIVERSITY   (Taiwan)

Author keywords

4 Aza steroids; Lactam; p Toluenesulfonic acid

Indexed keywords

CARBOXYLIC ACIDS; SYNTHESIS (CHEMICAL);

LACTAM FORMATION;

DRUG PRODUCTS;

4 AZA 3 OXO ANDROSTANE 17BETA CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; LACTAM; METHYL 3 (2,4 DIMETHOXYLBENZYLAMINE) 5 OXO A NOR 3,4 SECO ANDROSTANE 17BETA CARBOXYLATE; METHYL 3 OXO 4 ANDROSTENE 17BETA CARBOXYLIC ACID; STEROID; STEROID 5ALPHA REDUCTASE INHIBITOR; TOLUENESULFONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BENZYLATION; CHEMICAL MODIFICATION; CHEMICAL REACTION; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME SYNTHESIS; REACTION ANALYSIS;

EID: 2342418009     PISSN: 10161015     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (11)

1. Kenny, B.; Ballard, S.; Blagg, J; Fox, D. Pharmacological options in the treatment of benign prostatic hyperplasia. J. Med. Chem. 1997, 40, 1291.
2. Bolt, C. C. Darstellung Von Sterolderivaten Mit Kernsubstituiertem Stickstoff. Trav. Chim. Pays-Bas. 1938, 57, 905.
3. Windaus, A. Windas: Über Cholesterin. XXV. Mitteilung. Ber. 1917, 50, 133.
4. Miller, R. A.; Humphrey, G. B.; Thrompson, A. S. Stereocomplementary Reductions of Ring Fused Enelactams. Tetrahedron Lett. 1995, 36, 7949.
5. Bakshi, R. K.; Patel, G. F.; Rasmussen, G. H.; Baginsky, W. F.; Cimis, G.; Ellsworth, K.; Chang, B.; Bull, H.; Tolman, R. L.; Harris, G. S. 4,7-beta-Dimethyl-4-azacholestan-3-one (MK-386) and related 4-azasteroids as selective inhibitors of human type 15 alpha-reductase. J. Med. Chem. 1994, 37, 3871.
6. Hasserodt, J.; Janda, K. D.; Lerner, R. A. A class of 4-aza-lithocholic acid-derived haptens for the generation of catalytic antibodies with steroid synthase capabilities. Bioorg. Med. Chem. 2000, 8, 995.
7. Kurata, H.; Ishibaahi, K.; Saito, S.; Hamada, T.; Horikoshi, H.; Furukawa, Y.; Kojima, K. Synthesis and testosterone 5-a reductase-Inhibiotry Activity or 4-Aza-5a-androstane-17-carbaxamide Compound with an Aromatic Moiety in the C-17 Carbamoyl Group. Chem. Pharm. Bull. 1996, 44, 115.
8. Rasmussen, G. H.; Reynolds, G. F.; Steinberg, N. G.; Watson, E.; Patel, G. F.; Liang, T.; Cassieri, M. A.; Cheung, A. H.; Brooks, J. R.; Berman, C. Azasteroids: structure-activity relationships for inhibition of 5 alpha-reductase and of androgen receptor binding. J. Med. Chem. 1986, 29, 2298.
9. Fontane, E.; Angiuli, P.; Pignatti, A.; Panzeri, A.; Dostert, P. Synthesis of carbon-14 labelled 1-[4-methyl-3-mxo-4-AZA-5-androstane-17-carbonyl]-1,3-diisopropylurea (turosteride), a new 5-reductase inhibitor. J. Laballed Compd. Radiopharm. 1996, 38, 667.
10. Xia, P.; Yang, Z.-Y.; Xia, Y.; Zhang, H.-B.; Zhang, K.-H.; Sun, X.; Chen, Y.; Zheng, Y.-Q. Medicinal Foodstuffs. XIII. Saponin Constituents with Adjuvant Activity from Hyacinth Bean, The Seeds of Dolichos Lablab L. (2): Structures of Lablabosides D, E, and F. Heterocycles 1998, 47, 703.
11. Chern, C.-Y.; Huang, Y.-P.; Kan, W. M. Selective N-debenzylation of amides with p-TsOH. Tetrahedron Lett. 2003, 44, 1039.