Solid-phase synthesis of a library of amphipatic hydantoins. Discovery of new hits for TRPV1 blockade

ACS Combinatorial Science

Volumn 13, Issue 5, 2011, Pages 458-465

  Gerona Navarro, Guillermo ^a   González Muñiz, Rosario ^a   Fernández Carvajal, Asia ^b   González Ros, José M ^b   Ferrer Montiel, Antonio ^b,c   Carreño, Cristina ^c   Albericio, Fernando ^d,e   Royo, Miriam ^e  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^b MIGUEL HERNÁNDEZ UNIVERSITY   (Spain)

^c DiverDrugs SL ^*  (Spain)

^d INSTITUTE FOR RESEARCH IN BIOMEDICINE   (Spain)

^e UNIVERSITY OF BARCELONA   (Spain)

Author keywords

guanidine groups; Hydantoins; pain; solid phase; TRPV1 blockers

Indexed keywords

HYDANTOIN DERIVATIVE; N METHYL DEXTRO ASPARTIC ACID RECEPTOR; TRPV1 RECEPTOR; VANILLOID RECEPTOR;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; DRUG DEVELOPMENT; MOLECULAR LIBRARY; SOLID PHASE SYNTHESIS; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

DRUG DISCOVERY; HYDANTOINS; MOLECULAR STRUCTURE; RECEPTORS, N-METHYL-D-ASPARTATE; SMALL MOLECULE LIBRARIES; SOLID-PHASE SYNTHESIS TECHNIQUES; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP; TRPV CATION CHANNELS;

EID: 80052728666     PISSN: 21568952     EISSN: None     Source Type: Journal    
DOI: 10.1021/co1000986     Document Type: Article

References (60)

1. López, C. A.; Trigo, G. G. In Advances in Heterocyclic Chemistry; Brown, C., Davidson, R. M., Eds.; Academic Press: New York, 1985; Vol. 38, pp 177-228.
2. Kiec-Kononowicz, K.; Szymanska, E. Antimycobacterial activity of 5-arylidene derivatives of hydantoin Il Farmaco 2002, 57, 909-916
3. Carmi, C.; Cavazzoni, A.; Zuliani, V.; Lodola, A.; Bordi, F.; Plazzi, P. V.; Alfieri, R. R.; Petroni, P. G.; Mor, M. 5-Benzylidene-hydantoins as new EGFR inhibitors with antiproliferative activity Bioorg. Med. Chem. Lett. 2006, 16, 4021-4025 (Pubitemid 43903211)
4. Bakalova, A.; Buyukliev, R.; Tcholakova, I.; Momekov, G.; Kostantinov, S.; Karavanova, M. Synthesis, physicochemical investigation and cytotoxic activity of new Pt(II) complexes with hydantoin ligands Eur. J. Med. Chem. 2003, 38, 627-632 (Pubitemid 36773867)
5. Opacic, N.; Barbaric, M.; Zorc, B.; Cetina, M.; Nagl, A.; Frkovic, D.; Kralj, M.; Pavelic, K.; Balzarini, J.; Andrei, G.; Snoeck, R.; De Clercq, E.; Raic-Malic, S.; Mintas, M. Peptidyl 3-substituted 1-hydroxyureas as isosteric analogues of succinylhydroxamate MMP inhibitors J. Med. Chem. 2005, 48, 475-482
6. Jansen, M.; Potschka, H.; Brandt, C.; Löscher, W.; Dannhardt, G. Hydantoin-substituted 4,6-dichloroindole-2-carboxylic acids as ligands with high affinity for the glycine binding site of the NMDA receptor J. Med. Chem. 2003, 46, 64-73 (Pubitemid 36050069)
7. Zha, C.; Brown, G. B.; Brouillette, W. J. Synthesis and SAR studies for hydantoins and analogues as voltage-gated sodium channel ligands J. Med. Chem. 2004, 47, 6519-6528 (Pubitemid 39657314)
8. Last-Barney, K.; Davidson, W.; Cardozo, M.; Frye, L. L.; Grygon, C. A.; Hopkins, J. L.; Jeanfavre, D. D.; Pav, S.; Quian, C.; Stevenson, J. M.; Tong, L.; Zindell, R.; Kelly, T. A. Binding site elucidation of hydantoin-based antagonists of LFA-1 using multidisciplinary technologies: evidence for the allosteric inhibition of a protein-protein interaction J. Am. Chem. Soc. 2001, 123, 5643-5650 (Pubitemid 32904697)
9. Potin, D.; Launay, M.; Nicolai, E.; Fabreguette, M.; Malabre, P.; Caussade, F.; Besse, D.; Skala, S.; Stetsko, D. K.; Todderud, G.; Reno, B. R.; Cheney, D. L.; Chang, C. J.; Sheriff, S.; Hollenbaugh, D. L.; Barrish, J. C.; Iwanowicz, E. J.; Suchard, S. J.; Dhar, T. G. M. De novo design, synthesis, and in vitro activity of LFA-1 antagonists based on a bicyclic[5.5]hydantoin scaffold Bioorg. Med. Chem. Lett. 2005, 15, 1161-1164 (Pubitemid 40458666)
10. Evans, B. E.; Rittle, K. E.; Bock, M. G.; DiPardo, R. M.; Freidinger, R. M.; Whitter, W. L.; Lundell, G. F.; Veber, D. F.; Anderson, P. S.; Chang, R. S. L.; Lotti, V. J.; Cerino, D. J.; Chen, T. B.; Kling, P. J.; Kunkel, K. A.; Springer, J. P.; Hirsfield, J. Methods for drug discovery: development of potent, selective, orally effective cholecystokinin antagonists J. Med. Chem. 1988, 31, 2235-2246 (Pubitemid 19001640)
11. Meusel, M.; Gütschow, M. Recent Developments in Hydantoin Chemistry. A Review Org. Prep. Proced. Int. 2004, 36, 391-443 (Pubitemid 39531414)
12. Reyes, S.; Burgess, K. On Formation of Thiohydantoins from Amino Acids under Acylation Conditions J. Org. Chem. 2006, 71, 2507
13. Murray, R. G.; Whitehead, D.; Le Strat, F.; Conway, S. J. Facile one-pot synthesis of 5-substituted hydantoins Org. Biomol. Chem. 2008, 6, 988
14. Hulme, C.; Ma, L.; Romano, J. J.; Morton, G.; Tang, S.-Y.; Cherrier, M.-P.; Choi, S.; Salvino, J.; Labaudiniere, R. Novel applications of convertible isonitriles for the synthesis of mono and bicyclic γ -lactams via a UDC strategy Tetrahedron Lett. 2000, 41, 1889-1893
15. Zhang, W.; Lu, Y.; Chen, H.-T.; Zeng, L.; Kassel, D. B. Fluorous Mixture Synthesis of Two Libraries with Hydantoin- and Benzodiazepinedione-Fused Heterocyclic Scaffolds J. Comb. Chem. 2006, 8, 687-695 (Pubitemid 44578625)
16. DeWitt, H. S.; Kiely, J. S.; Stankovic, C. J.; Schroeder, M. C.; Cody, D. M. R.; Pavia, M. R. "Diversomers": an approach to nonpeptide, nonoligomeric chemical diversity Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 6909-6913 (Pubitemid 23222357)
17. Mattews, J.; Rivero, R. A. Base-Promoted Solid-Phase Synthesis of Substituted Hydantoins and Thiohydantoins J. Org. Chem. 1997, 62, 6090-6092 (Pubitemid 27375222)
18. Kim, S. W.; Ahn, S. Y.; Koh, J. S.; Lee, J. H.; Ro, S.; Cho, H. Y. Solid phase synthesis of hydantoin library using a novel cyclization and traceless cleavage step Tetrahedron Lett. 1997, 38, 4603-4606 (Pubitemid 27263312)
19. Kim, S. W.; Koh, J. S.; Lee, E. J.; Ro, S. Solid phase synthesis of benzamidine and butylamine-derived hydantoin libraries Mol. Diversity 1998, 3, 129-132
20. Boeijen, A.; Kruijtzer, J. A. W.; Liskamp, R. M. J. Combinatorial chemistry of hydantoins Bioorg. Med. Chem. Lett. 1998, 8, 2375-2380 (Pubitemid 28551499)
21. Karnbrock, W.; Deeg, M.; Gerhardt, J.; Rapp, W. Solid phase synthesis of hydantoins by thermal cyclization and screening of reaction conditions using APOS 1200 Mol. Diversity 1998, 3, 165-171 (Pubitemid 128514161)
22. Gong, Y.-D.; Najdi, S.; Olmstead, M. M.; Kurth, M. J. Solid-Phase Synthesis: Intramolecular Azomethine Ylide Cycloaddition (→Proline) and Carbanilide Cyclization (→Hydantoin) Reactions J. Org. Chem. 1998, 63, 3081-3086 (Pubitemid 28216696)
23. 3-alkylated hydantoins from solid-phase: synthesis of novel isoxazoloimidazolidinediones Tetrahedron Lett. 1999, 40, 5841-5844 (Pubitemid 29343835)
24. Huang, W.; Cheng, S.; Sun, W. 2-Polystyrylsulfonyl ethanol supports for the solid-phase syntheses of hydantoins and ureas Tetrahedron Lett. 2001, 42, 1973-1974 (Pubitemid 32179582)
25. Park, K.-H.; Ehrler, J.; Spoerri, H.; Kurth, M. J. Preparation of a 990-Member Chemical Compound Library of Hydantoin- and Isoxazoline-Containing Heterocycles Using Multipin Technology J. Comb. Chem. 2001, 3, 171-176 (Pubitemid 33614501)
26. Lamothe, M.; Lannuzel, M.; Perez, M. Solid-Phase Preparation of Hydantoins through a New Cyclization/Cleavage Step J. Comb. Chem. 2002, 4, 73-78
27. Alsina, J.; Scott, W. L.; O'Donnell, M. J. Solid-phase synthesis of α-substituted proline hydantoins and analogs Tetrahedron Lett. 2005, 46, 3131-3135 (Pubitemid 40445449)
28. Kuster, G. J. T.; van Berkom, L. W. A.; Kalmoua, M.; van Loevezijn, A.; Sliedregt, L. A. J. M.; van Steen, B. J.; Kruse, C. G.; Rutjes, F. P. J. T.; Scheeren, H. W. Synthesis of Spirohydantoins and Spiro-2,5-diketopiperazines via Resin-Bound Cyclic α,α-Disubstituted α-Amino Esters J. Comb. Chem. 2006, 8, 85-94 (Pubitemid 43166086)
29. Yeh, W.-P.; Chang, W.-J.; Sun, M.-L.; Sun, C.-M. Microwave-assisted traceless synthesis of hydantion-fused β-carboline scaffold Tetrahedron 2007, 63, 11809-11816 (Pubitemid 47575636)
30. Dressman, B. A.; Spangle, L. A.; Kaldor, S. W. Solid phase synthesis of hydantoins using a carbamate linker and a novel cyclization/cleavage step Tetrahedron Lett. 1996, 37, 937-940
31. Xiao, X.-Y.; Ngu, K.; Chao, C.; Patel, D. V. Selective Solid Phase Synthesis of Ureas and Hydantoins from Common Phenyl Carbamate Intermediates J. Org. Chem. 1997, 62, 6968-6973 (Pubitemid 127494632)
32. Chong, P. Y.; Petillo, P. A. Solid phase hydantoin synthesis: An efficient and direct conversion of Fmoc-protected dipeptides to hydantoins Tetrahedron Lett. 1999, 40, 2493-2496 (Pubitemid 29130515)
33. Bhalay, G.; Cowell, D.; Hone, N. D.; Scobie, M.; Baxter, A. D. Multiple solid-phase synthesis of hydantoins and thiohydantoins Mol. Diversity 1997, 3, 195-198 (Pubitemid 127507553)
34. Nefzi, A.; Dooley, C.; Ostresh, J. M.; Houghten, R. A. Combinatorial chemistry: From peptides and peptidomimetics to small organic and heterocyclic compounds Bioorg. Med. Chem. Lett. 1998, 8, 2273-2278 (Pubitemid 28551482)
35. Nefzi, A.; Ostresh, J. M.; Giulianotti, M.; Houghten, R. A. Efficient solid phase synthesis of 3,5-disubstituted hydantoins Tetrahedron Lett. 1998, 39, 8199-8202 (Pubitemid 28480126)
36. Nefzi, A.; Giulianotti, M.; Truong, L.; Rattan, S.; Ostresh, J. M.; Houghten, R. A. Solid-Phase Synthesis of Linear Ureas Tethered to Hydantoins and Thiohydantoins J. Comb. Chem. 2002, 4, 175-178
37. Severinsen, R.; Lau, J. F.; Bondensgaard, K.; Hansen, B. S.; Begtrup, M.; Ankersen, M. Parallel solid-phase synthesis of disubstituted (5-biphenyltetrazolyl) hydantoins and thiohydantoins targeting the growth hormone secretagogue receptor Bioorg. Med. Chem. Lett. 2004, 14, 317-320 (Pubitemid 38045113)
38. 3 integrin receptor Tetrahedron Lett. 2001, 42, 7387-7391 (Pubitemid 32913341)
39. 3 Enzyme Subsite ChemMedChem 2008, 3, 979-985
40. Ekelund, S.; Nygren, P.; Larsson, R. Guanidino-containing drugs in cancer chemotherapy: biochemical and clinical pharmacology Biochem. Pharmacol. 2001, 61, 1183-1193 (Pubitemid 32375110)
41. Ravaud, A.; Cerny, T.; Terret, C.; Wanders, J.; Bui, B. N.; Hess, D.; Droz, J.-P.; Fumoleau, P.; Twelves, C. Phase I study and pharmacokinetic of CHS-828, a guanidino-containing compound, administered orally as a single dose every 3 weeks in solid tumours: An ECSG/EORTC study Eur. J. Cancer 2005, 41, 702-707 (Pubitemid 40342552)
42. Sienczyk, M.; Oleksyszyn, J. Inhibition of trypsin and urokinase by Cbz-amino(4-guanidinophenyl)methanephosphonate aromatic ester derivatives: The influence of the ester group on their biological activity Bioorg. Med. Chem. Lett. 2006, 16, 2886-2890 (Pubitemid 44316651)
43. Katsura, Y.; Nishino, Y.; Inoue, Y.; Sakane, K.; Matsumoto, Y.; Morinaga, C.; Ishikawa, H.; Takasugi, H. Anti- Helicobacter pylori agents. 5. 2-(substituted guanidino)-4-arylthiazoles and Aryloxazole Analogues J. Med. Chem. 2002, 45, 143-150
44. Oh, C.-H.; Cho, J.-H. Synthesis and biological evaluation of 1β-methylcarbapenems having guanidino moieties Eur. J. Med. Chem. 2006, 41, 50-55 (Pubitemid 43276058)
45. Masuda, T.; Yoshida, S.; Arai, M.; Kaneko, S.; Yamashita, M.; Honda, T. Synthesis and anti-influenza evaluation of polyvalent pialidase inhibitors bearing 4-guanidino-Neu5Ac2en derivatives Chem. Pharm. Bull. 2003, 51, 1386-1398 (Pubitemid 41694755)
46. Huang, H.; Martasek, P.; Roma, L. J.; Silverman, R. B. Synthesis and evaluation of peptidomimetics as selective inhibitors and active site probes of Nitric Oxide Synthases J. Med. Chem. 2000, 43, 2938-2945 (Pubitemid 30599652)
47. Lam, P. Y. S.; Clark, C. G.; Li, R.; Pinto, D. J. P.; Orwat, M. J.; Galemmo, R. A.; Fevig, J. M.; Teleha, C. A.; Alexander, R. S.; Smallwood, A. M.; Rossi, K. A.; Wright, M. R.; Bai, S. A.; He, K.; Luettgen, J. M.; Wong, P. C.; Knabb, R. M.; Wexler, R. R. Structure-based design of novel guanidine/ benzamidine mimics: potent and orally bioavailable factor Xa inhibitors as novel anticoagulants J. Med. Chem. 2003, 46, 4405-4418 (Pubitemid 37238744)
48. 2 receptor antagonists and synthase Inhibitors J. Med. Chem. 1999, 42, 1235-1249 (Pubitemid 29181146)
49. Lack, S. L.; Chaovignac, C.; Grundt, P.; Miller, C. N.; Wood, S.; Traynor, J. R.; Lewis, J. W.; Husbands, S. M. Guanidino N-substituted and N,N-disubstituted derivatives of the κ-opioid antagonist GNTI J. Med. Chem. 2003, 46, 5505-5511 (Pubitemid 37490381)
50. Suagse, K.; Horikawa, M.; Sugiyama, M.; Ishiguro, M. Restriction of a peptide turn conformation and Conformational analysis of guanidino group using arginine-proline fused amino acids: application to mini Atrial Natriuretic peptide on binding to the receptor J. Med. Chem. 2004, 47, 489-492 (Pubitemid 38057890)
51. + exchanger isoform-1 J. Med. Chem. 2005, 48, 2882-2891 (Pubitemid 40552910)
52. Del Fresno, M.; El-Faham, A.; Carpino, L. A.; Royo, M.; Albericio, F. Substituted guanidines: introducing diversity in combinatorial chemistry Org. Lett. 2000, 2, 3539-3542
53. Vázquez, J.; Royo, M.; Albericio, F. Re-evaluation of a solid-phase hydantoin synthesis Lett. Org. Chem. 2004, 1, 224-226
54. Caterina, M. J.; Julius, D. The Vanilloid receptor: a molecular gateway to the pain pathway Annu. Rev. Neurosci. 2001, 24, 487-517 (Pubitemid 32695237)
55. Jara-Oseguera, A.; Simon, S. A.; Rosenbaum, T. TRPV1: on the road to pain relief Curr. Mol. Pharmacol. 2008, 1, 255-269
56. Szallasi, A.; Cortright, D. N.; Blum, C. A.; Eid, S. R. The vanilloid receptor TRPV1: 10 years from channel cloning to antagonist proof-of-concept Nat. Rev. Drug Discovery 2007, 6, 357-372 (Pubitemid 46705200)
57. Messeguer, A.; Planells-Cases, R.; Ferrer-Montiel, A. Physiology and pharmacology of the vanilloid receptor Curr. Neuropharmacol. 2006, 4, 1-5
58. Garcia-Martinez, C.; Fernández-Carvajal, A.; Valenzuela, B.; Gomis, A.; Van Den Nest, W.; Ferroni, S.; Carreño, C.; Belmonte, C.; Ferrer-Montiel, A. Design and characterization of a non competitive antagonist of the TRVP1channel with in vivo analgesic and anti-inflammatory activity J. Pain 2006, 7, 735-746 (Pubitemid 44472626)
59. Albensi, B. C. The NMDA receptor/ion channel complex: a drug target for modulating synaptic plasticity and excitotoxicity Curr. Pharm. Des. 2007, 13, 3185-3194 (Pubitemid 350201695)
60. García-Martínez, C.; Humet, M.; Planells-Cases, R.; Gomis, A.; Caprini, M.; Viana, F.; De la Peña, E.; Sanchez-Baeza, F.; Carbonell, T.; De Felipe, C.; Pérez-Payá, E.; Belmonte, C.; Messeguer, A.; Ferrer-Montiel, A. Attenuation of thermal nociception and hyperalgesia by VR1 blockers Proc. Natl. Acad. Sci. U.S.A. 2002, 99, 2374-2379 (Pubitemid 34169068)