Steroidomimetic tetrahydroisoquinolines for the design of new microtubule disruptors

ACS Medicinal Chemistry Letters

Volumn 3, Issue 1, 2012, Pages 5-9

  Leese, Mathew P ^a   Jourdan, Fabrice ^a   Dohle, Wolfgang ^a   Kimberley, Meriel R ^a   Thomas, Mark P ^a   Bai, Ruoli ^b   Hamel, Ernest ^b   Ferrandis, Eric ^c   Potter, Barry V L ^a  

^a University of Bath   (United Kingdom)

^b NATIONAL CANCER INSTITUTE   (United States)

^c IPSEN   (France)

Author keywords

microtubule disruptor; steroidomimetic; structure activity relationship; Tetrahydroisoquinoline

Indexed keywords

COMBRETASTATIN A4; TETRAHYDROISOQUINOLINE DERIVATIVE;

ARTICLE; BURKITT LYMPHOMA; CANCER CELL; CELL PROLIFERATION; CONTROLLED STUDY; HUMAN; HUMAN CELL; HYDROGEN BOND; MICROTUBULE; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PROSTATE CANCER;

EID: 84863422019     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml200232c     Document Type: Article

References (20)

1. Jordan, M. A.; Wilson, L. Microtubules as a target for anticancer drugs Nat. Rev. Cancer 2004, 4, 253-265 (Pubitemid 38525281)
2. Hadfield, J. A.; Ducki, S.; Hirst, N.; McGown, A. T.; Meijer, L.; Jezequel, A.; Roberge, M. Progress in Cell Cycle Research Prog. Cell Cycle Res. 2003, 309-325
3. Reed, M. J.; Purohit, A.; Newman, S. P.; Potter, B. V. L. Steroid sulfatase: molecular biology, regulation, and inhibition Endocr. Rev. 2005, 26, 171-202
4. Purohit, A.; Hejaz, H. A. M.; Walden, L.; MacCarthy-Morrogh, L.; Packham, G.; Potter, B. V. L; Reed, M. J. The effect of 2-methoxyoestrone-3- O -sulphamate on the growth of breast cancer cells and induced mammary tumours Int. J. Cancer 2000, 85, 584-589 (Pubitemid 30075140)
5. Leese, M. P.; Hejaz, H. A. M.; Mahon, M. F.; Newman, S. P.; Purohit, A.; Reed, M. J.; Potter, B. V. L. A-ring-substituted estrogen-3- O -sulfamates: potent multitargeted anticancer agents J. Med. Chem. 2005, 48, 5243-5256 (Pubitemid 41113911)
6. MacCarthy-Morrogh, L.; Townsend, P. A.; Purohit, A.; Hejaz, H. A. M.; Potter, B. V. L; Reed, M. J.; Packham, G. Differential effects of estrone and estrone-3- O -sulfamate derivatives on mitotic arrest, apoptosis, and microtubule assembly in human breast cancer cells Cancer Res. 2000, 60, 5441-5450
7. Ireson, C. R.; Chander, S. K.; Purohit, A.; Perera, S.; Newman, S. P.; Parish, D.; Leese, M. P.; Smith, A. C.; Potter, B. V. L; Reed, R. J. Pharmacokinetics and efficacy of 2-methoxyoestradiol and 2-methoxyoestradiol- bis-sulphamate in vivo in rodents Br. J. Cancer 2004, 90, 932-937 (Pubitemid 38406609)
8. Jourdan, F.; Leese, M. P.; Dohle, W.; Hamel, E.; Ferrandis, E.; Newman, S. P.; Purohit, A.; Reed, M. J.; Potter, B. V. L. Synthesis, Antitubulin, and Antiproliferative SAR of Analogues of 2-Methoxyestradiol-3,17- O, O -bis-sulfamate J. Med. Chem. 2010, 53, 2942-2951
9. Leese, M. P.; Newman, S. P.; Purohit, A.; Reed, M. J.; Potter, B. V. L. 2-Alkylsulfanyl estrogen derivatives: synthesis of a novel class of multi-targeted anti-tumour agents Bioorg. Med. Chem. Lett. 2004, 14, 3135-3138 (Pubitemid 38624578)
10. Leese, M. P.; Leblond, B.; Newman, S. P.; Purohit, A.; Reed, M. J.; Potter, B. V. L. Anti-cancer activities of novel D-ring modified 2-substituted estrogen-3- O -sulfamates J. Steroid Biochem. Mol. Biol. 2005, 94, 239-251 (Pubitemid 40614537)
11. Leese, M. P.; Leblond, B.; Smith, A.; Newman, S. P.; Di Fiore, A.; De Simone, G.; Supuran, C. T.; Purohit, A.; Reed, M. J.; Potter, B. V. L. 2-Substituted estradiol bis-sulfamates, multitargeted antitumor agents: synthesis, in vitro SAR, protein crystallography, and in vivo activity J. Med. Chem. 2006, 49, 7683-7696 (Pubitemid 46033660)
12. Leese, M. P.; Jourdan, F. L.; Gaukroger, K.; Mahon, M. F.; Newman, S. P.; Foster, P. A.; Stengel, C.; Regis-Lydi, S.; Ferrandis, E.; Di Fiore, A.; De Simone, G.; Supuran, C. T.; Purohit, A.; Reed, M. J.; Potter, B. V. L. Structure-activity relationships of C-17 cyano-substituted estratrienes as anticancer agents. J. Med. Chem. 2008, 51, 1295-1308 (Pubitemid 351480390)
13. Jourdan, F.; Bubert, C.; Leese, M. P.; Smith, A.; Ferrandis, E.; Regis-Lydi, S.; Newman, S. P.; Purohit, A.; Reed, M. J.; Potter, B. V. L. Effects of C-17 heterocyclic substituents on the anticancer activity of 2-ethylestra-1,3,5(10)-triene-3- O -sulfamates: synthesis, in vitro evaluation and computational modelling Org. Biomol. Chem. 2008, 6, 4108-4119
14. Bubert, C.; Leese, M. P.; Mahon, M. F.; Ferrandis, E.; Regis-Lydi, S.; Kasprzyk, P. G.; Newman, S. P.; Ho, Y. T.; Purohit, A.; Reed, M. J.; Potter, B. V. L. 3,17-Disubstituted 2-alkylestra-1,3,5(10)-trien-3-ol derivatives: synthesis, in vitro and in vivo anticancer activity J. Med. Chem. 2007, 50, 4431-4443 (Pubitemid 47378840)
15. Chesworth, R.; Zawistoski, M. P.; Lefker, B. A.; Cameron, K. O.; Day, R. F.; Mangano, M.; Rosati, R. L.; Colella, S.; Petersen, D. N.; Brault, A.; Lu, B. H.; Pan, L. C.; Perry, P.; Ng, O.; Castleberry, T. A.; Owen, T. A.; Brown, T. A.; Thompson, D. D.; DaSilva-Jardine, P. Tetrahydroisoquinolines as subtype selective estrogen agonists/antagonists Bioorg. Med. Chem. Lett. 2004, 14, 2729-2733 (Pubitemid 38569728)
16. Leese, M. P.; Jourdan, F.; Kimberley, M. R.; Cozier, G. E.; Thiyagarajan, N.; Stengel, C.; Regis-Lydi, S.; Foster, P. A.; Newman, S. P.; Acharya, K. R.; Ferrandis, E.; Purohit, A.; Reed, M. J.; Potter, B. V. L. Chimeric microtubule disruptors Chem. Comm. 2010, 46, 2907-2909
17. Cox, E. D.; Cook, J. M. The Pictet-Spengler condensation: a new direction for an old reaction Chem. Rev. 1995, 95, 1797-1842
18. Schlosser, M.; Simig, G.; Geneste, H. Three complementary methods offering access to 5-substituted 1,2,3,4-tetrahydroisoquinolines Tetrahedron 1998, 54, 9023-9032 (Pubitemid 28319965)
19. Zhong, H. M.; Villani, F. J.; Marzouq, R. Improved and Practical Synthesis of 6-Methoxy-1,2,3,4-tetrahydroisoquinoline Hydrochloride Org. Process Res. Dev. 2007, 11, 463-465
20. Cruz-Monserrate, Z.; Vervoort, H. C.; Bai, R. L.; Newman, D. J.; Howell, S. B.; Los, G.; Mullaney, J. T.; Williams, M. D.; Pettit, G. R.; Fenical, W.; Hamel, E. Diazonamide A and a Synthetic Structural Analog: Disruptive Effects on Mitosis and Cellular Microtubules and Analysis of Their Interactions with Tubulin Mol. Pharmacol. 2003, 63, 1273-1280 (Pubitemid 36627221)