Nonsteroidal androgen receptor ligands: Versatile syntheses and biological data

ACS Medicinal Chemistry Letters

Volumn 3, Issue 6, 2012, Pages 454-458

  Varchi, Greta ^a   Guerrini, Andrea ^a   Tesei, Anna ^b   Brigliadori, Giovanni ^b   Bertucci, Carlo ^c   Di Donato, Marzia ^d   Castoria, Gabriella ^d  

^a CNR   (Italy)

^b DEPARTMENT OF MEDICAL ONCOLOGY   (Italy)

^c UNIVERSITY OF BOLOGNA   (Italy)

^d UNIVERSITY OF NAPLES FEDERICO II   (Italy)

Author keywords

androgen receptor; enantiopure antiandrogens; hormone refractory prostate cancer; sulfinylimino propanamides

Indexed keywords

ANTIANDROGEN; BICALUTAMIDE; LIGAND; NITROGEN; OXYGEN;

APOPTOSIS; ARTICLE; BIOLOGICAL ACTIVITY; CONTROLLED STUDY; CYCLIZATION; CYTOTOXICITY; DRUG EFFECT; DRUG RECEPTOR BINDING; DRUG STRUCTURE; DRUG SYNTHESIS; FLOW CYTOMETRY; HUMAN; HUMAN CELL; LIGAND BINDING; PRIORITY JOURNAL;

EID: 84862275888     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml3000269     Document Type: Article

References (26)

1. Gooren, L. J. G.; Bunck, M. C. M. Androgen Replacement Therapy: Present and Future Drugs 2004, 64, 1861-1891 (Pubitemid 39243569)
2. Gao, W.; Dalton, J. T. Expanding the therapeutic use of androgens via selective androgen receptor modulators (SARMs) Drug Discovery Today 2007, 12, 241-248
3. Kelly, W. K.; Scher, H. I. Prostate specific antigen decline after antiandrogen withdrawal: The flutamide withdrawal syndrome J. Urol. 1993, 149, 607-609 (Pubitemid 23094069)
4. Schellhammer, P. F.; Venner, P.; Haas, G. P.; Small, E. J.; Nieh, P. T.; Seabaugh, D. R.; Patterson, A. L.; Klein, E.; Wajsman, Z.; Furr, B.; Chen, Y.; Kolvenbag, G. J. Prostate Specific Antigen Decreases After Withdrawal of Antiandrogen Therapy with Bicalutamide or Flutamide in Patients Receiving Combined Androgen Blockade J. Urol. 1997, 157, 1731-1735 (Pubitemid 27171763)
5. Jung, M.; Ouk, S.; Yoo, D.; Sawyers, C.; Chen, C.; Tran, C.; Wongvipat, J. Structure-Activity Relationship for Thiohydantoin Androgen Receptor Antagonists for Castration-Resistant Prostate Cancer (CRPC) J. Med. Chem. 2010, 53, 2779-2796
6. Chen, C. D.; Welsbie, D. S.; Tran, C.; Baek, S. H.; Chen, R.; Vessella, R.; Rosenfeld, M. G.; Sawyers, C. L. Molecular determinants of resistance to antiandrogen therapy Nat. Med. 2004, 10, 33-39 (Pubitemid 38524696)
7. Marhefka, C. A.; Gao, W.; Chung, K.; Kim, J.; He, Y.; Yin, D.; Bohl, C.; Dalton, J. T.; Miller, D. D. Design, Synthesis, and Biological Characterization of Metabolically Stable Selective Androgen Receptor Modulators J. Med. Chem. 2004, 47, 993-998 (Pubitemid 38176802)
8. Dalton, J.; Miller, D.; Rakov, I.; Bohl, C. Selective Androgen Receptor Modulators, analogs and derivatives threof and uses thereof. WO/2008/011,072, 2008.
9. Jones, A.; Chen, J.; Hwang, D.; Miller, D.; Dalton, J. Preclinical Characterization of a (S)-N -(4-Cyano-3-Trifluoromethyl-Phenyl)-3-(3-Fluoro, 4-Chlorophenoxy)-2-Hydroxy -2-Methyl-Propanamide: A Selective Androgen Receptor Modulator for Hormonal Male Contraception Endocrinology 2009, 150, 385-39
10. Hwang, D.; Yang, J.; Xu, H.; Rakov, I.; Mohler, M.; Dalton, J.; Miller, D. Arylisothiocyanato selective androgen receptor modulators (SARMs) for prostate cancer Bioorg. Med. Chem. 2006, 14, 6525-6538 (Pubitemid 44233324)
11. Cogan, D. A.; Liu, G.; Kim, K.; Backes, B. J.; Ellman, J. A. Catalytic Asymmetric Oxidation of tert -Butyl Disulfide. Synthesis of tert -Butanesulfinamides, tert -Butyl Sulfoxides, and tert -Butanesulfin imines J. Am. Chem. Soc. 1998, 120, 8011-8019
12. Liu, G.; Cogan, D. A.; Owens, T. D.; Tang, T. P.; Ellman, J. A. Synthesis of Enantiomerically Pure N-tert -Butanesulfinyl Imines (tert -Butanesulfin imines) by the Direct Condensation of tert -Butanesulfinamide with Aldehydes and Ketones J. Org. Chem. 1999, 64, 1278-1284 (Pubitemid 29098570)
13. Ellman, J. A.; Robak, M. T.; Herbage, M. A. Synthesis and Applications of tert -Butanesulfinamide Chem. Rev. 2010, 110, 3600-3740 and references therein
14. Chen, B.; Zhao, R.; Gove, S.; Wang, B.; Sundeen, J. E.; Salvati, M. E.; Barrish, J. C. Nucleophilic Aromatic Substitution of Methacrylamide Anion and Its Application to the Synthesis of the Anticancer Drug Bicalutamide J. Org. Chem. 2003, 68, 10181-10182 (Pubitemid 38017882)
15. James, K.; Ekwuribe, N. A Two-step Synthesis of the Anti-cancer Drug (R, S)-Bicalutamide Synthesis 2002, 850-853
16. Parent, E. E.; Dence, C. S.; Jenks, C.; Sharp, T. L.; Welch, M. J.; Katzenellenbogen, J. A. Synthesis and Biological Evaluation of [18F]Bicalutamide, 4-[76Br]Bromobicalutamide, and 4-[76Br] Bromo- thiobicalutamide as Non-Steroidal Androgens for Prostate Cancer Imaging J. Med. Chem. 2007, 1028-1040 (Pubitemid 46394005)
17. Liu, J.; Hu, J. Highly Diastereoselective Synthesis of a-Difluoromethyl Amines from N-tert-Butylsulfinyl Ketimines and Difluoromethyl Phenyl Sulfone Chem.-Eur. J. 2010, 16, 11443-11454
18. Veldscholte, J.; Berrevoets, C.; Ris-Stalpers, C. The Androgen receptor contains a mutation in the ligand binding domain which affects steroid binding characteristics and response to antiandrogens J. Steroid Biochem. Mol. Biol. 1992, 41, 665-669
19. Horoszewics, J. S.; Leong, S. S.; Kawinski, E.; Karr, J. P.; Rosenthal, H.; Chu, T. M.; Miraud, E. A.; Murphy, G. P. LNCaP Model of Human Prostatic Carcinoma Cancer Res. 1983, 48, 1809-1818 (Pubitemid 13122588)
20. Sawyers, C. L.; Jung, M. E.; Chen, C. D.; Ouk, S.; Welsbie, D.; Tran, C.; Wongvipat, J.; Yoo, D. Diarylhydantoin compounds. U.S. Patent Appl. 20070004753, 2007.
21. Higano, C. S.; Beer, T. M.; Hung, D. T.; Scher, H. I.; Jung, M. E.; Sawyers, C. L. Development of a Second-Generation Antiandrogen for Treatment of Advanced Prostate Cancer Science 2009, 324, 787-790
22. Chen, Y.; Clegg, N.; Scher, H. Anti-androgens and androgen-depleting therapies in prostate cancer: new agents for an established target Lancet Oncol. 2009, 10, 981-991
23. Skehan, P.; Storeng, R.; Scudiero, D.; Monks, A.; McMahon, J.; Vistica, D. New colorimetric cytotoxicity assay for anticancer-drug screening J. Natl. Cancer Inst. 1990, 82, 1107-12 (Pubitemid 20213250)
24. Castoria, G.; D'Amato, L.; Ciociola, A.; Giovannelli, P.; Giraldi, T.; Sepe, L.; Paolella, G.; Barone, M. V.; Migliaccio, A.; Auricchio, F. Androgen-induced cell migration: role of androgen receptor/filamin A association PLoS One 2011, 6, e17218
25. Concellón, J. M.; Rodríguez-Solla, H.; Bernad, P. L.; Simal, C. Addition Reactions of Chloro- or Iodomethyllithium to Imines. Synthesis of Enantiopure Aziridines and b-Chloroamines J. Org. Chem. 2009, 74, 2452-2459
26. Colpaert, F.; Mangelinckx, S.; Leemans, E.; Denolf, B.; De Kimpe, N. Asymmetric synthesis of new chiral N -sulfinyl 2,2-disubstituted aziridines by Grignard additions across α-chloro N -sulfinyl ketimines Org. Biomol. Chem. 2010, 8, 3251-3258