Searching for novel applications of the benzohomoadamantane scaffold in medicinal chemistry: Synthesis of novel 11β-HSD1 inhibitors

Bioorganic and Medicinal Chemistry

Volumn 23, Issue 24, 2015, Pages 7607-7617

  Valverde, Elena ^a   Seira, Constantí ^a   McBride, Andrew ^b   Binnie, Margaret ^b   Luque, F Javier ^a   Webster, Scott P ^b   Bidon Chanal, Axel ^a   Vázquez, Santiago ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

^b UNIVERSITY OF EDINBURGH   (United Kingdom)

Author keywords

11 HSD1 inhibitors; Adamantane; Cage compounds; Drug discovery; Molecular dynamics

Indexed keywords

1 ETHYL N (9 FLUORO 6,7,8,9,10,11 HEXAHYDRO 5H 5,9:7,11 DIMETHANOBENZO[9]ANNULEN 7 YL)PYRROLIDINE 2 CARBOXAMIDE; 1 ETHYL N (9 HYDROXY 6,7,8,9,10,11 HEXAHYDRO 5H 5,9:7,11 DIMETHANOBENZO[9]ANNULEN 7 YL)PYRROLIDINE 2 CARBOXAMIDE; 1 ETHYL N (9 METHYL 6,7,8,9,10,11 HEXAHYDRO 5H 5,9:7,11 DIMETHANOBENZO[9]ANNULEN 7 YL)PYRROLIDINE 2 CARBOXAMIDE; 11 BETA HYDROXYSTEROID DEHYDROGENASE 1 INHIBITOR DERIVATIVE; 4 AMINO 3,5 DICHLORO N (9 HYDROXY 6,7,8,9,10,11 HEXAHYDRO 5H 5,9:7,11 DIMETHANOBENZO[9]ANNULEN 7 YL)BENZAMIDE; 4 AMINO 3,5 DICHLORO N (9 METHYL 6,7,8,9,10,11 HEXAHYDRO 5H 5,9:7,11 DIMETHANOBENZO[9]ANNULEN 7 YL)BENZAMIDE; 5,5 DIMETHYL 2 [(9 METHYL 5,6,8,9,10,11 HEXAHYDRO 5H 5,9:7,11 DIMETHANOBENZO[9]ANNULEN 7 YL)AMINO]THIAZOL 4 (5H)ONE; AGENTS AFFECTING METABOLISM; BENZOHOMOADAMANTANE; ENZYME INHIBITOR; MOLECULAR SCAFFOLD; N (9 FLUORO 6,7,8,9,10,11 HEXAHYDRO 5H 5,9:7,11 DIMETHANOBENZO[9]ANNULEN 7 YL)PIPERIDINE 1 CARBOXAMIDE; N (9 HYDROXY 6,7,8,9,10,11 HEXAHYDRO 5H 5,9:7,11 DIMETHANOBENZO[9]ANNULEN 7 YL)PIPERIDINE 1 CARBOXAMIDE; N (9 HYDROXY 6,7,8,9,10,11 HEXAHYDRO 5H 5,9:7,11 DIMETHANOBENZO[9]ANNULEN 7 YL)PYRROLIDINE 2 CARBOXAMIDE; N (9 METHOXY 6,7,8,9,10,11 HEXAHYDRO 5H 5,9:7,11 DIMETHANOBENZO[9]ANNULEN 7 YL)PIPERIDINE 1 CARBOXAMIDE; N (9 METHYL 5,6,8,9,10,11 HEXAHYDRO 5H 5,9:7,11 DIMETHANOBENZO[9]ANNULEN 7 YL)CYCLOHEXANECARBOXAMIDE; N (9 METHYL 5,6,8,9,10,11 HEXAHYDRO 5H 5,9:7,11 DIMETHANOBENZO[9]ANNULEN 7 YL)THIOUREA; N (9 METHYL 6,7,8,9,10,11 HEXAHYDRO 5H 5,9:7,11 DIMETHANOBENZO[9]ANNULEN 7 YL)PIPERIDINE 1 CARBOXAMIDE; N (9 METHYL 6,7,8,9,10,11 HEXAHYDRO 5H 5,9:7,11 DIMETHANOBENZO[9]ANNULEN 7 YL)PYRROLIDINE 2 CARBOXAMIDE; PF 877423; TERT BUTYL 2 [(9 HYDROXY 6,7,8,9,10,11 HEXAHYDRO 5H 5,9:7,11 DIMETHANOBENZO[9]ANNULEN 7 YL)CARBAMOYL]PYRROLIDINE 1 CARBOXYLATE; TERT BUTYL 2 [(9 METHYL 6,7,8,9,10,11 HEXAHYDRO 5H 5,9:7,11 DIMETHANOBENZO[9]ANNULEN 7 YL)CARBAMOYL]PYRROLIDINE 1 CARBOXYLATE; UNCLASSIFIED DRUG; 11BETA HYDROXYSTEROID DEHYDROGENASE 1; ADAMANTANE;

ARTICLE; BINDING AFFINITY; BINDING SITE; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; DRUG DESIGN; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME INHIBITION; HUMAN; HUMAN CELL; HYDROGEN BOND; HYDROPHOBICITY; IN VITRO STUDY; INFRARED SPECTROSCOPY; LIVER MICROSOME; MASS SPECTROMETRY; MEDICINAL CHEMISTRY; MOLECULAR DYNAMICS; MOLECULAR MODEL; PARTICLE SIZE; PHYSICAL CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; ANALOGS AND DERIVATIVES; ANTAGONISTS AND INHIBITORS; CHEMISTRY; DRUG DEVELOPMENT; METABOLISM; SYNTHESIS;

11-BETA-HYDROXYSTEROID DEHYDROGENASE TYPE 1; ADAMANTANE; DRUG DISCOVERY; ENZYME INHIBITORS; HUMANS; MOLECULAR DYNAMICS SIMULATION;

EID: 84949527636     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2015.11.004     Document Type: Article

References (59)

1. S. Landa Chem. Listy 27 1933 415
2. S. Landa Chem. Listy 27 1933 443
3. R.C. Fort Jr., R. von, and P. Schleyer Chem. Rev. 64 1964 277
4. G. Lamoureux, and G. Artavia Curr. Med. Chem. 17 2010 2967
5. L. Wanka, K. Iqbal, and P.R. Schreiner Chem. Rev. 113 2013 3516
6. T.P. Stockdale, and C.M. Williams Chem. Soc. Rev. 44 2015 7737
7. W.L. Davies, R.R. Grunert, R.F. Haff, J.W. McGahen, E.M. Neumayer, M. Paulshock, J.C. Watts, T.R. Wood, E.C. Hermann, and C.E. Hoffmann Science 144 1964 862
8. A. Tsunoda, H.F. Maassab, K.W. Cochran, and W.C. Eveland Antimicrob. Agents Chemother. (1961-70) 5 1965 553
9. W. Danysz, and C.G. Parsons Br. J. Pharmacol. 167 2012 324
10. E.B. Villhauer, J.A. Brinkman, G.B. Naderi, B.F. Burkey, B.E. Dunning, K. Prasad, B.L. Mangold, M.E. Russell, and T.E. Hughes J. Med. Chem. 46 2003 2774
11. D.J. Augeri, J.A. Robl, D.A. Betebenner, D.R. Magnin, A. Khanna, J.G. Robertson, A. Wang, L.M. Simpkins, P. Taunk, Q. Huang, S.-P. Han, B. Abboa-Offei, M. Cap, L. Xin, L. Tao, E. Tozzo, G.E. Welzel, D.M. Egan, J. Marcinkeviciene, S.Y. Chang, S.A. Biller, M.S. Kirby, R.A. Parker, and L.G. Hamann J. Med. Chem. 48 2005 5025
12. A. Anderson, and B.R. Walker Drugs 73 2013 1385
13. J.S. Scott, F.W. Goldberg, and A.V. Turnbull J. Med. Chem. 57 2014 4466
14. J.D. Imig, and B.D. Hammock Nat. Rev. Drug Disc. 8 2009 794
15. H.C. Shen, and B.D. Hammock J. Med. Chem. 55 2012 1789
16. T. Duflot, C. Roche, F. Lamoureux, D. Guerrot, and J. Bellien Expert Opin. Drug Discov. 9 2014 229
17. C. Fotsch, and M. Wang J. Med. Chem. 51 2008 4851
18. M. Wang Drug Dev. Res. 67 2006 567
19. S.M. Grundy, H.B. Brewer, J.I. Cleeman, S.C. Smith, and C. Lenfant Circulation 109 2004 433
20. G. Valsamakis, A. Anwar, J.W. Tomlinson, C.H.L. Shackleton, P.G. McTernan, R. Chetty, P.J. Wood, A.K. Banerjee, G. Holder, A.H. Barnett, P.M. Stewart, and S. Kumar J. Clin. Endocrinol. Metab. 89 2004 4755
21. J.S. Scott, and J. Chooramun 11β-Hydroxysteroid Dehydrogenase Type 1 (11β-HSD1) inhibitors in Development R.M. Jones, New Therapeutic Strategies for Type 2 Diabetes Small Molecule Approaches, RSC Drug Discovery Series No Vol. 27 2012 Royal Society of Chemistry Cambridge 109 141
22. D.J. Hosfield, Y. Wu, R.J. Skene, M. Hilgers, A. Jennings, G.P. Snell, and K. Aertgeerts J. Biol. Chem. 280 2005 4639
23. J. Zhang, T.D. Osslund, M.H. Plant, C.L. Clogston, R.E. Nybo, F. Xiong, J.M. Delaney, and S.R. Jordan Biochemistry 44 2005 6948
24. M.P. Thomas, and B.V.L. Potter Future Med. Chem. 3 2011 367
25. S.P. Webster, and T.D. Pallin Expert Opin. Ther. Pat. 17 2007 1407
26. F.A. Rubio, N. Choma, and E.K. Fukuda J. Chromatogr. 497 1989 147
27. H. Su, D.W. Boulton, Anthony Barros Jr., L. Wang, K. Cao, S.J. Bonacorsi Jr., R.A. Iyer, W.G. Humphreys, and L.J. Christopher Drug Metab. Dispos. 40 2012 1345
28. X. Gu, J. Dragovic, G.C. Koo, S.L. Koprak, C. Legrand, S.S. Mundt, K. Shah, M.S. Springer, E.Y. Tan, R. Thieringer, A. Hermanowski-Vosatka, H.J. Zokian, J.M. Balkovec, and S.T. Waddell Bioorg. Med. Chem. Lett. 15 2005 5266
29. L. Johansson, C. Fotsch, M.D. Bartberger, V.M. Castro, M. Chen, M. Emery, S. Gustafsson, C. Hale, D. Hickman, E. Homan, S.R. Jordan, R. Komorowski, A. Li, K. McRae, G. Moniz, G. Matsumoto, C. Orihuela, G. Palm, M. Veniant, M. Wang, M. Williams, and J. Zhang J. Med. Chem. 51 2008 2933
30. M.M. Véniant, C. Hale, R.W. Hungate, K. Gahm, M.G. Emery, J. Jona, S. Joseph, J. Adams, A. Hague, G. Moniz, J. Zhang, M.D. Bartberger, V. Li, R. Syed, S. Jordan, R. Komorowski, M.M. Chen, R. Cupples, K.W. Kim, D.J. St Jean, L. Johansson, M.A. Henriksson, M. Williams, J. Vallgårda, C. Fotsch, and M. Wang J. Med. Chem. 53 2010 4481
31. M. Maletic, A. Leeman, M. Szymonifka, S.S. Mundt, H.J. Zokian, K. Shah, J. Dragovic, K. Lyons, R. Thieringer, A.H. Vosatka, J. Balkovec, and S.T. Waddell Bioorg. Med. Chem. Lett. 21 2011 2568
32. X.-Y. Ye, S.Y. Chen, A. Nayeem, R. Golla, R. Seethala, M. Wang, T. Harper, B.G. Sleczka, B. He, D.A. Gordon, and J.A. Robl Bioorg. Med. Chem. Lett. 21 2011 6699
33. G. Xia, L. Liu, M. Xue, H. Liu, J. Yu, P. Li, Q. Chen, B. Xiong, X. Liu, and J. Shen Mol. Cell. Endocrinol. 358 2012 46
34. D.R. Bauman, A. Whitehead, L.C. Contino, J. Cui, M. García-Calvo, X. Gu, N. Kevin, X. Ma, L.-Y. Pai, K. Shah, X. Shen, S. Stribling, H.J. Zokian, J. Metzger, D.E. Shevell, and S.T. Waddell Bioorg. Med. Chem. Lett. 23 2013 3650 3653
35. P. Camps, M.D. Duque, S. Vázquez, L. Naesens, E. De Clercq, F.S. Sureda, M. López-Querol, A. Camins, M. Pallàs, S.R. Prathalingam, J.M. Kelly, V. Romero, D. Ivorra, and D. Cortés Bioorg. Med. Chem. 16 2008 9925
36. M.D. Duque, P. Camps, L. Profire, S. Montaner, S. Vázquez, F.S. Sureda, J. Mallol, M. López-Querol, L. Naesens, E. De Clercq, S.R. Prathalingam, and J.M. Kelly Bioorg. Med. Chem. 17 2009 3198
37. M.D. Duque, C. Ma, E. Torres, J. Wang, L. Naesens, J. Juárez-Jiménez, P. Camps, F.J. Luque, W.F. DeGrado, R.A. Lamb, L.H. Pinto, and S. Vázquez J. Med. Chem. 54 2011 2646
38. M. Rey-Carrizo, E. Torres, C. Ma, M. Barniol-Xicota, J. Wang, Y. Wu, L. Naesens, W.F. DeGrado, R.A. Lamb, L.H. Pinto, and S. Vázquez J. Med. Chem. 56 2013 9265
39. E. Torres, R. Leiva, S. Gazzarrini, M. Rey-Carrizo, M. Frigolé-Vivas, A. Moroni, L. Naesens, and S. Vázquez ACS Med. Chem. Lett. 5 2014 831
40. M. Rey-Carrizo, M. Barniol-Xicota, C. Ma, M. Frigolé-Vivas, E. Torres, L. Naesens, S. Llabrés, J. Juárez-Jiménez, F.J. Luque, W.F. DeGrado, R.A. Lamb, L.H. Pinto, and S. Vázquez J. Med. Chem. 57 2014 5738
41. M. Rey-Carrizo, S. Gazzarrini, S. Llabrés, M. Frigolé-Vivas, J. Juárez-Jiménez, M. Font-Bardia, L. Naesens, A. Moroni, F.J. Luque, and S. Vázquez Eur. J. Med. Chem. 96 2015 318
42. M.D. Duque, P. Camps, E. Torres, E. Valverde, F.X. Sureda, M. López-Querol, A. Camins, S.R. Prathalingam, J.M. Kelly, and S. Vázquez Bioorg. Med. Chem. 18 2010 46
43. E. Torres, M.D. Duque, M. López-Querol, M.C. Taylor, L. Naesens, C. Ma, L.H. Pinto, F.X. Sureda, J.M. Kelly, and S. Vázquez Bioorg. Med. Chem. 20 2012 942
44. E. Valverde, F.X. Sureda, and S. Vázquez Bioorg. Med. Chem. 22 2014 2678
45. S. Richards, B. Sorensen, H. Jae, M. Winn, Y. Chen, J. Wang, S. Fung, K. Monzon, E.U. Frevert, P. Jacobson, H. Sham, and J.T. Link Bioorg. Med. Chem. Lett. 16 2006 6241
46. H. Cheng, J. Hoffman, P. Le, S.K. Nair, S. Cripps, J. Matthews, C. Smith, M. Yang, S. Kupchinsky, K. Dress, M. Edwards, B. Cole, E. Walters, C. Loh, J. Ermolieff, A. Fanjul, G.B. Bhat, J. Herrera, T. Pauly, N. Hosea, G. Paderes, and P. Rejto Bioorg. Med. Chem. Lett. 20 2010 2897
47. C.M. Tice, W. Zhao, Z. Xu, S.T. Cacatian, R.D. Simpson, Y.-J. Ye, S.B. Singh, B.M. McKeever, P. Lindblom, J. Guo, P.M. Krosky, B.A. Kruk, J. Berbaum, R.K. Harrison, J.J. Johnson, Y. Bukhtiyarov, R. Panemangalore, B.B. Scott, Y. Zhao, J.G. Bruno, L. Zhuang, G.M. McGeehan, W. He, and D.A. Claremon Bioorg. Med. Chem. Lett. 20 2010 881
48. R. Leiva, C. Seira, A. McBride, M. Binnie, F.J. Luque, A. Bidon-Chanal, S.P. Webster, and S. Vázquez Bioorg. Med. Chem. Lett. 25 2015 4250
49. R.A. Friesner, R.B. Murphy, M.P. Repasky, L.L. Frye, J.R. Greenwood, T.A. Halgren, P.C. Sanschagrin, and D.T. Mainz J. Med. Chem. 49 2006 6177
50. M. Gülden, S. Mörchel, and H. Seibert Toxicol. In Vitro 15 2001 233
51. C. Curutchet, M. Orozco, and F.J. Luque J. Comput. Chem. 22 2001 1180
52. F.W. Goldberg, A.G. Leach, J.S. Scott, W.L. Snelson, S.D. Groombridge, C.S. Donald, S.N.L. Bennett, C. Bodin, P. Morentin Gutierrez, and A.C. Gyte J. Med. Chem. 55 2012 10652
53. W.L. Jorgensen, J. Chandrasekhar, J.D. Madura, R.W. Impey, and M.L. Klein J. Chem. Phys. 79 1983 926
54. V. Hornak, R. Abel, A. Okur, B. Strockbine, A. Roitberg, and C. Simmerling Proteins 65 2006 712
55. K. Lindorff-Larsen, S. Piana, K. Palmo, P. Maragakis, J.L. Klepeis, R.O. Dror, and D.E. Shaw Proteins 78 2010 1950
56. J. Wang, R.M. Wolf, J.W. Caldwell, P.A. Kollman, and D.A. Case J. Comput. Chem. 25 2004 1157
57. J.-P. Ryckaert, G. Ciccotti, and H.J.C. Berendsen J. Comput. Phys. 23 1977 327
58. I. Soteras, C. Curutchet, A. Bidon-Chanal, M. Orozco, and F.J. Luque J. Mol. Struct. Theochem. 727 2005 29
59. M. Kolar, J. Fanfril, M. Lepsik, F. Fort, F.J. Luque, and P. Hobza J. Phys. Chem. B 117 2013 5950