3-(3,4-dihydroisoquinolin-2(1 H)-ylsulfonyl)benzoic acids: Highly potent and selective inhibitors of the type 5 17-β-hydroxysteroid dehydrogenase AKR1C3

Journal of Medicinal Chemistry

Volumn 55, Issue 17, 2012, Pages 7746-7758

  Jamieson, Stephen M F ^a   Brooke, Darby G ^a   Heinrich, Daniel ^a   Atwell, Graham J ^a   Silva, Shevan ^a   Hamilton, Emma J ^a   Turnbull, Andrew P ^b   Rigoreau, Laurent J M ^c   Trivier, Elisabeth ^c   Soudy, Christelle ^c   Samlal, Sharon S ^c   Owen, Paul J ^c   Schroeder, Ewald ^c   Raynham, Tony ^c   Flanagan, Jack U ^a   Denny, William A ^a  

^a UNIVERSITY OF AUCKLAND   (New Zealand)

^b UNIVERSITY OF LONDON   (United Kingdom)

^c UNIVERSITY COLLEGE LONDON   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

3 [3,4 DIHYDROISOQUINOLIN 2(1H)YLSULFONYL]BENZOIC ACID; 3 [[5,6 DIHYDROPYRIDIN 1(2H)YL]SULFONYL]BENZOIC ACID; AMIDE; BENZOIC ACID DERIVATIVE; CARBOXYLIC ACID; FLUFENAMIC ACID; FLURBIPROFEN; IBUPROFEN; INDOMETACIN; MECLOFENAMIC ACID; NAPROXEN; SULFONAMIDE; TESTOSTERONE 17BETA DEHYDROGENASE; UNCLASSIFIED DRUG;

ARTICLE; CELL ACTIVITY; CELL ASSAY; CRYSTAL STRUCTURE; DRUG BINDING; DRUG EFFICACY; DRUG POTENCY; DRUG SCREENING; ENZYME ACTIVITY; ENZYME METABOLISM; HIGH THROUGHPUT SCREENING; HUMAN; HUMAN CELL; HYDROPHOBICITY; IC 50; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION;

3-HYDROXYSTEROID DEHYDROGENASES; BENZOATES; ENZYME INHIBITORS; HUMANS; HYDROXYPROSTAGLANDIN DEHYDROGENASES; MODELS, MOLECULAR; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84866336135     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm3007867     Document Type: Article

References (40)

1. Barski, O. A.; Tipparaju, S. M.; Bhatnagar, A. The aldo-keto reductase superfamily and its role in drug metabolism and detoxification Drug Met. Rev. 2008, 40, 553-624
2. Penning, T. M.; Burczynski, M. E.; Jez, J. M.; Hung, C.-F.; Lin, H.-K.; Ma, H.; Moore, M.; Palackal, N.; Ratnam, K. Human 3α-hydroxysteroid dehydrogenase isoforms (AKR1C1-AKR1C4) of the aldo-keto reductase superfamily: functional plasticity and tissue distribution reveals roles in the inactivation and formation of male and female sex hormones Biochem. J. 2000, 351, 67-77
3. Komoto, J.; Yamada, T.; Watanabe, K.; Takusagawa, F. Crystal structure of human prostaglandin F synthase (AKR1C3) Biochemistry 2004, 43, 2188-2198 (Pubitemid 38279964)
4. Desmond, J. C.; Mountford, J. C.; Drayson, M. T.; Walker, E. A.; Hewison, M.; Ride, J. P.; Luong, Q. T.; Hayden, R. E.; Vanin, E. F.; Bunce, C. M. The aldo-keto reductase AKR1C3 is a novel suppressor of cell differentiation that provides a plausible target for the non-cyclooxygenase-dependent antineoplastic actions of nonsteroidal anti-inflammatory drugs Cancer Res. 2003, 63, 505-512 (Pubitemid 36152514)
5. Novotna, R.; Wsol, V.; Xiong, G.; Maser, E.. Inactivation of the anticancer drugs doxorubicin and oracin by aldo-keto reductase (AKR)1C3 Toxicol. Lett. 2008, 181, 1-6
6. Guise, C. P.; Abbattista, M. R.; Singleton, R. S.; Holford, S. D.; Connolly, J.; Dachs, G. U.; Fox, S. B.; Pollock, R.; Harvey, J.; Guilford, P.; Donate, F.; Wilson, W. R.; Patterson, A. V. The bioreductive prodrug PR-104A is activated under aerobic conditions by human aldo-keto reductase 1C3 Cancer Res. 2010, 70, 1573-1584
7. Steckelbroeck, S.; Jin, Y.; Gopishetty, S.; Oyesanmi, B.; Penning, T. M. Human cytosolic 3α-hydroxysteroid dehydrogenases of the aldo-keto reductase superfamily display significant 3β-hydroxysteroid dehydrogenase activity: implications for steroid hormone metabolism and action J. Biol. Chem. 2003, 279, 10784-10795 (Pubitemid 38379543)
8. Penning, T. M.; Steckelbroeck, S.; Bauman, D. R.; Miller, M. W.; Jin, Y.; Peehl, D. M.; Fung, K. M.; Lin, H. K. Aldo-keto reductase AKR1C3: role in prostate disease and the development of specific inhibitors Mol. Cell. Endocrinol. 2006, 248 (1-2) 182-191
9. Brozic, P.; Turk, S.; Rizner, T. L.; Gobec, S. Inhibitors of aldo-keto reductases AKR1C1-AKR1C4 Curr. Med. Chem. 2011, 18, 2554-2565
10. Byrns, M. C.; Jin, Y.; Penning, T. M. Inhibitors of type 5 17β-hydroxysteroid dehydrogenase (AKR1C3): Overview and structural insight J. Steroid Biochem. Mol. Biol. 2011, 125, 95-104
11. Davies, N. J.; Hayden, R. E.; Simpson, P. J.; Birtwistle, J.; Mayer, K.; Ride, J. P.; Bunce, C. M. AKR1C isoforms represent a novel cellular target for jasmonates alongside their mitochondrial-mediated effects Cancer Res. 2009, 69, 4769-4775
12. Stefane, B.; Brozic, P.; Vehovc, M.; Rizner, T. L.; Gobec, S. New cyclopentane derivatives as inhibitors of steroid metabolizing enzymes AKR1C1 and AKR1C3 Eur. J. Med. Chem. 2009, 44, 2563-2571
13. Adeniji, A. O.; Twenter, B. M.; Byrns, M. C.; Jin, Y.; Chen, M.; Winkler, J. D.; Penning, T. M. Development of potent and selective inhibitors of aldo-keto reductase 1C3 (type 5 17β-hydroxysteroid dehydrogenase) based on N-phenyl-aminobenzoates and their structure-activity relationships J. Med. Chem. 2012, 55, 2311-2323
14. Komoto, J.; Yamada, T.; Watanabe, K.; Takusagawa, F. Crystal structure of human prostaglandin F synthase (AKR1C3) Biochemistry 2004, 43, 2188-2198 (Pubitemid 38279964)
15. Skarydova, L.; Zivna, L.; Xiong, G.; Maser, E.; Wsol, V. AKR1C3 as a potential target for the inhibitory effect of dietary flavonoids Chem.-Biol. Interact. 2009, 178, 138-144
16. Endo, S.; Matsunaga, T.; Kanamori, A.; Otsuji, Y.; Nagai, H.; Sundaram, K.; El-Kabbani, O.; Toyooka, N.; Ohta, S.; Hara, A. Selective inhibition of human type-5 17β-hydroxysteroid dehydrogenase (AKR1C3) by baccharin, a component of Brazilian propolis J. Nat. Prod. 2012, 75, 716-721
17. Adeniji, A. O.; Twenter, B. M.; Byrns, M. C.; Jin, Y.; Winkler, J. D.; Penning, T. M. Discovery of substituted 3-(phenylamino)benzoic acids as potent and selective inhibitors of type 5 17β-hydroxysteroid dehydrogenase (AKR1C3) Bioorg. Med. Chem. Lett. 2011, 21, 1464-1468
18. Xu, X. C. Cox-2 inhibitors in cancer treatment and prevention, a recent development Anti-Cancer Drugs 2002, 13, 127-137
19. Lovering, A. L.; Ride, J. P.; Bunce, C. M.; Desmond, J. C.; Cummings, S. M.; White, S. A. Crystal structures of prostaglandin D2 11-ketoreductase (AKR1C3) in complex with the nonsteroidal anti-inflammatory drugs flufenamic acid and indomethacin Cancer Res. 2004, 64, 1802-1810 (Pubitemid 38428705)
20. Byrns, M. C.; Penning, T. M. Type 5 17β-hydroxysteroid dehydrogenase/prostaglandin F synthase (AKR1C3): Role in breast cancer and inhibition by non-steroidal anti-inflammatory drug analogs Chem.-Biol. Interact. 2009, 178, 221-227
21. Kakefuda, A.; Kondoh, Y.; Hirano, M.; Kamikawa, A.; Enjo, K.; Furutani, T. Benzimidazole derivatives. WO 2009/014150 A1, published June 29th, 2009.
22. Shearer, B. G.; Patel, H. S.; Billin, A. N.; Way, J. M.; Winegar, D. A.; Lambert, M. H.; Xu, R. X.; Leesnitzer, L. M.; Merrihew, R. V.; Huet, S.; Willson, T. M. Discovery of a novel class of PPARδ partial agonists Bioorg. Med. Chem. Lett. 2008, 18, 5018-5022
23. Isabel, E.; Black, W. C.; Bayly, C. I.; Grimm, E. L.; Janes, M. K.; McKay, D. J.; Nicholson, D. W.; Rasper, D. M.; Renaud, J.; Roy, S.; Tam, J.; Thornberry, N. A.; Vaillancourt, J. P.; Xanthoudakis, S.; Zamboni, R. Nicotinyl aspartyl ketones as inhibitors of caspase-3 Bioorg. Med. Chem. Lett. 2003, 13, 2137-2140 (Pubitemid 36694291)
24. Black, C.; Grimm, E. L.; Isabel, E.; Renaud, J. Nicotinyl aspartyl ketones as inhibitors of caspase-3. Patent WO 01/27085 A1, 2001.
25. Pu, Y.-M.; Christesen, A.; Ku, Y.-Y. A simple and highly effective oxidative chlorination protocol for the preparation of arenesulfonyl chlorides Tetrahedron Lett. 2010, 51, 418
26. Byrns, M. C.; Steckelbroeck, S.; Penning, T. M. An indomethacin analogue, N -(4-chlorobenzoyl)-melatonin, is a selective inhibitor of aldo-keto reductase 1C3 (type 2 3α-HSD, type 5 17β-HSD, and prostaglandin F synthase), a potential target for the treatment of hormone dependent and hormone independent malignancies Biochem. Pharmacol. 2008, 75, 484-493 (Pubitemid 350298472)
27. Orazi, O. O.; Corral, R. A.; Giaccio, H. Synthesis of fused heterocycles: 1,2,3,4-tetrahydroisoquinolines and ring homologues via sulphonamidomethylation J. Chem. Soc., Perkin Trans. 1 1986, 1977
28. Feng, D.-J.; Wang, P.; Li, X.-Q.; Li, Z.-T. Self-assembly of hydrazide-based heterodimers driven by hydrogen bonding and donor-acceptor interaction Chin. J. Chem. 2006, 24, 1200-1208
29. Myers, A. G.; Dragovich, P. S. Synthesis of functionalises enynes by palladium/copper-catalyzed coupling reactions of acetylenes with (Z)-2,3-dibromopropenoic acid ethyl ester: (Z)-2-bromo-5-(trimethylsilyl)-2- penten-4-ynoic acid ethyl ester Org. Synth. 1995, 72, 104-111
30. Nicolaou, K. C.; Tang, Y.; Wang, J. Total synthesis of sporolide B Angew. Chem., Int. Ed. 2009, 48, 3449-3453
31. Gu, Z.; Li, Z.; Liu, Z.; Wang, Y.; Liu, C.; Xiang, J. Simple, efficient copper-free Sonogashira coupling of haloaryl carboxylic acids or unactivated aryl bromides with terminal alkynes Catal. Commun. 2008, 9, 2154-2157
32. Nakamura, T.; Sato, M.; Kakinuma, H.; Miyata, N.; Taniguchi, K.; Bando, K.; Koda, A.; Kameo, K. Pyrazole and isoxazole derivatives as new, potent, and selective 20-hydroxy-5,8.11,14-eicosatetraenoic acid synthase inhibitors J. Med. Chem. 2003, 46, 5416-5427 (Pubitemid 37490374)
33. Zhou, M.; Wei Qiu, W.; Chang, H.-J.; Gangloff, A.; Lin, S.-X. Purification, crystallization and preliminary X-ray diffraction results of human 17β-hydroxysteroid dehydrogenase type 5 Acta Crystallogr. 2002, D58, 1048-1050 (Pubitemid 34653040)
34. McCoy, A. J.; Grosse-Kunstleve, R. W.; Adams, P. D.; Winn, M. D.; Storoni, L. C.; Read, R. J. Phaser crystallographic software J. Appl. Crystallogr. 2007, 40, 658-674 (Pubitemid 47080256)
35. Emsley, P.; Cowtan, K. Coot: model-building tools for molecular graphics Acta Crystallogr. 2004, D60, 2126-2132 (Pubitemid 41742764)
36. Murshudov, G. N.; Lebedev, A.; Vagin, A. A.; Wilson, K. S.; Dodson, E. J. Efficient anisotropic refinement of Macromolecular structures using FFT Acta Crystallogr. 1999, D55, 247-255 (Pubitemid 29053823)
37. Yee, D. J.; Balsanek, V.; Sames, D. New tools for molecular imaging of redox metabolism: development of a fluorogenic probe for 3α-hydroxysteroid dehydrogenases J. Am. Chem. Soc. 2004, 126, 2282-2283 (Pubitemid 38295689)
38. Yang, S.; Atwell, G. J.; Denny, W. A. Synthesis of asymmetric halomesylate mustards with aziridineethanol/alkali metal halides: application to an improved synthesis of the hypoxia prodrug PR-104 Tetrahedron 2007, 63, 5470-5476 (Pubitemid 46778867)
39. 2H4-labelled versions of the hypoxia-activated pre-prodrug 2-[(2-bromoethyl)-2,4-dinitro-6-[[[2-(phosphonooxy)ethyl]amino] carbonyl]anilino]ethyl methanesulfonate (PR-104) J. Labelled Compd. Radiopharm. 2007, 50, 7-12 (Pubitemid 46456784)
40. Singleton, R. S.; Guise, C. P.; Ferry, D. M.; Pullen, S. M.; Dorie, M. J.; Brown, J. M.; Patterson, A. V.; Wilson, W. R. DNA cross-links in human tumor cells exposed to the prodrug PR-104A: relationships to hypoxia, bioreductive metabolism, and cytotoxicity Cancer Res. 2009, 69, 3884-3891