Novel P45017α inhibitors: 17-(2′-oxazolyl)- and 17-(2′-thiazolyl)-androstene derivatives

Steroids

Volumn 68, Issue 7-8, 2003, Pages 603-611

  Zhu, Na ^a   Ling, Yangzhi ^a   Lei, Xiaoping ^a   Handratta, Venkatesh ^b   Brodie, Angela M H ^b  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^b UNIVERSITY OF MARYLAND SCHOOL OF MEDICINE   (United States)

Author keywords

17 (2 Oxazolyl) androstenes; 17 (2 Thiazolyl) androstenes; P45017 inhibitors; Prostatic cancer

Indexed keywords

17 (2' OXAZOLYL)ANDROSTA 5,16 DIENE; 17 (2' THIAZOLYL)ANDROSTA 5,16 DIENE; 17 (5' ISOXAZOLYL)PREGNA 4,16 DIENE 3,20 DIONE; 3BETA ACETOXY 17 (2' THIAZOLYL)ANDROSTA 5,16 DIENE; 3BETA ACETOXYL 17 (2' OXAZOLYL)ANDROSTA 5,16 DIENE; 3BETA ACETOXYPREGNA 5,16 DIEN 20 ONE; 3BETA HYDROXY 17 (5' METHYL 2' THIAZOLYL)ANDROSTA 5,16 DIENE; ANDROSTANE DERIVATIVE; ANTINEOPLASTIC AGENT; CYTOCHROME P450; CYTOCHROME P450 17ALPHA; CYTOCHROME P450 INHIBITOR; L 39; METHYL GROUP; PHENYL GROUP; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; ENZYME INHIBITOR; RECOMBINANT PROTEIN; STEROID 17ALPHA MONOOXYGENASE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CHEMICAL BOND; CONTROLLED STUDY; DRUG DESIGN; DRUG POTENCY; DRUG SYNTHESIS; ENZYME ASSAY; ENZYME INHIBITION; NONHUMAN; PROSTATE CARCINOMA; STRUCTURE ACTIVITY RELATION; DRUG ANTAGONISM; ESCHERICHIA COLI; GENETICS; HUMAN; MALE; PROSTATE TUMOR; SYNTHESIS;

ANDROSTENES; ANTINEOPLASTIC AGENTS; ENZYME INHIBITORS; ESCHERICHIA COLI; HUMANS; MALE; PROSTATIC NEOPLASMS; RECOMBINANT PROTEINS; STEROID 17-ALPHA-HYDROXYLASE; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0042737909     PISSN: 0039128X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0039-128X(03)00082-5     Document Type: Article

References (17)

1. Njar V.C.O., Brodie A.M.H. Inhibitors of 17α -hydroxylase/17,20-lyase (CYP17): potential agents for the treatment of prostate cancer. Curr. Pharm. Des. 5:1999;163-180.
2. Trachtenberg J. Ketoconazole therapy in advanced prostatic cancer. J. Urol. 132:1984;61-63.
3. Williams G., Kerle D.J., Doble A., Dunlop H., Smith C., Allen J.et al. Objective responses to ketoconazole therapy in patients with relapsed progressive prostatic cancer. Br. J. Urol. 58:1986;45-51.
4. 17α). J. Med. Chem. 40:1997;3297-3304.
5. 17α): potential agents for the treatment of prostate cancer. J. Med. Chem. 41:1998;902-912.
6. 17α by abiraterone (17-(3-pyridyl)androsta-5,16-diene-3β-ol) and related steroidal inhibitors. J. Med. Chem. 41:1998;5375-5381.
7. Urbansky M., Drasar P. Simple syntheses of steroidal 17β-(2′ -thiazolyl) derivatives. Syn. Commun. 23:1993;829-845.
8. Marker R.E., Wagner R.B. The hypoiodite oxidation of pregnanolones and pregnenolones. J. Am. Chem. Soc. 64:1942;1842-1843.
9. 5,16-3β-oxy-ätiocholadiensäure und einige ihrer umwandlungsprodukte. Helv. Chim. Acta. 27:1944;1164.
10. Preparation of bromoacetone. Org Syn Coll 2:88.
11. Hepworth JD. Aminoacetone semicarbazone hydrochloride. Org Synth Ol 45:1-3.
12. 5-aetiocholensäure: ein Beitrag zur verknüpfung der Androsteron mit der corticosteron-Gruppe. Ber. 71:1938;1487-1489.
13. Carroll L. Preparation of 21-pyridinium-3-β -hydroxy-5-pregnene-20-one halides and 3-β -hydroxy-5-androstene-17-carboxylic acid. J. Am. Chem. Soc. 66:1944;1612.
14. Vernin G. General synthetic methods for thiazole and thiazolium salts. In: Metzger JV, editor. Thiazole and its derivatives. New York: Interscience Publication; 1979. p. 169-209.
15. Turchi IJ. Synthesis and reactions of functionalized oxazoles. In: Metzger JV, editor. Oxazole and its derivatives. New York: Interscience Publication; 1979. p. 3.
16. Wipf P., Miller C.P. A new synthesis of highly functionalized oxazoles. J. Org. Chem. 58:1993;3604-3606.
17. 17,20-lyase inhibitors. Anal. Biochem. 267:1999;319-330.