Synthesis and structure - Activity relationships of N -(2-Oxo-3-oxetanyl) amides as N -acylethanolamine-hydrolyzing acid amidase inhibitors

Journal of Medicinal Chemistry

Volumn 53, Issue 15, 2010, Pages 5770-5781

  Solorzano, Carlos ^a   Antonietti, Francesca ^b   Duranti, Andrea ^b   Tontini, Andrea ^b   Rivara, Silvia ^c   Lodola, Alessio ^c   Vacondio, Federica ^c   Tarzia, Giorgio ^b   Piomelli, Daniele ^a,d   Mor, Marco ^c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b UNIVERSITY OF URBINO   (Italy)

^c UNIVERSITY OF PARMA   (Italy)

^d ISTITUTO ITALIANO DI TECNOLOGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDASE; CYSTEINE; ETHANOLAMINE; FATTY ACID; FATTY ACID AMIDASE; FATTY ACID AMIDASE INHIBITOR; LACTONE DERIVATIVE; N (2 OXO 3 OXETANYL) 3 PHENYLPROPIONAMIDE; N (2 OXO 3 OXETANYL)AMIDE DERIVATIVE; N (2 OXO 3 OXETANYL)BIPHENYL 4 CARBOXAMIDE; N ACYLETHANOLAMINE HYDROLYZING ACID AMIDASE; PALMIDROL; PEROXISOME PROLIFERATOR ACTIVATED RECEPTOR ALPHA AGONIST; UNCLASSIFIED DRUG;

ACYLATION; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; CATALYSIS; CELL INFILTRATION; CONTROLLED STUDY; DRUG POTENCY; DRUG SELECTIVITY; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME DEGRADATION; ENZYME INHIBITION; HUMAN; HUMAN CELL; HYDROLYSIS; IC 50; INFLAMMATION; LEUKOCYTE; MOLECULAR RECOGNITION; MOUSE; NONHUMAN; STRUCTURE ACTIVITY RELATION;

AMIDES; AMIDOHYDROLASES; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; BIPHENYL COMPOUNDS; CARRAGEENAN; CATALYTIC DOMAIN; CELL LINE; ETHERS, CYCLIC; HUMANS; HYDROLYSIS; INFLAMMATION; KINETICS; LACTONES; LEUKOCYTES; MICE; MODELS, MOLECULAR; RATS; RECOMBINANT PROTEINS; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77955405511     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100582w     Document Type: Article

References (67)

1. Russo, R.; LoVerme, J.; La Rana, G.; Compton, T. R.; Parrott, J.; Duranti, A.; Tontini, A.; Mor, M.; Tarzia, G.; Calignano, A.; Piomelli, D. The fatty acid amide hydrolase inhibitor URB597 (cyclohexylcarbamic acid 3'-carbamoylbiphenyl-3-yl ester) reduces neuropathic pain after oral administration in mice J. Pharmacol. Exp. Ther. 2007, 322, 236-242
2. McKinney, M. K.; Cravatt, B. F. Structure and function of fatty acid amide hydrolase Annu. Rev. Biochem. 2005, 74, 411-432
3. Di Marzo, V. Targeting the endocannabinoid system: to enhance or reduce? Nat. Rev. Drug Discovery 2008, 7, 438-455
4. Mazzari, S.; Canella, R.; Petrelli, L.; Marcolongo, G.; Leon, A. N -(2-Hydroxyethyl)hexadecanamide is orally active in reducing edema formation and inflammatory hyperalgesia by down-modulating mast cell activation Eur. J. Pharmacol. 1996, 300, 227-236
5. Calignano, A.; La Rana, G.; Giuffrida, A.; Piomelli, D. Control of pain initiation by endogenous cannabinoids Nature 1998, 394, 277-281
6. Lo Verme, J.; Fu, J.; Astarita, G.; La Rana, G.; Russo, R.; Calignano, A.; Piomelli, D. The nuclear receptor peroxisome proliferator-activated receptor-a mediates the anti-inflammatory actions of palmitoylethanolamide Mol. Pharmacol. 2005, 67, 15-19
7. LoVerme, J.; Russo, R.; La Rana, G.; Fu, J.; Farthing, J.; Mattace-Raso, G.; Meli, R.; Hohmann, A.; Calignano, A.; Piomelli, D. Rapid broad-spectrum analgesia through activation of peroxisome proliferator-activated receptor-a J. Pharmacol. Exp. Ther. 2006, 319, 1051-1061
8. Petrosino, S.; Iuvone, T.; Di Marzo, V. N -Palmitoyl-ethanolamine: biochemistry and new therapeutic opportunities Biochimie 2010, 92, 724-727
9. 1, TRPV1, and PPAR? receptors and neurotrophic factors Pain 2008, 139, 541-550
10. Bisogno, T.; Maurelli, S.; Melck, D.; De Petrocellis, L.; Di Marzo, V. Biosynthesis, uptake, and degradation of anandamide and palmitoylethanolamide in leukocytes J. Biol. Chem. 1997, 272, 3315-3323
11. Liu, J.; Wang, L.; Harvey-White, J.; Osei-Hyiaman, D.; Razdan, R.; Gong, Q.; Chan, A. C.; Zhou, Z.; Huang, B. X.; Kim, H.-Y.; Kunos, G. A biosynthetic pathway for anandamide Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 13345-13350
12. Ueda, N.; Yamanaka, K.; Yamamoto, S. Purification and characterization of an acid amidase selective for N -palmitoylethanolamine, a putative endogenous anti-inflammatory substance J. Biol. Chem. 2001, 276, 35552-35557
13. Tsuboi, K.; Sun, Y. X.; Okamoto, Y.; Araki, N.; Tonai, T.; Ueda, N. Molecular characterization of N -acylethanolamine-hydrolyzing acid amidase, a novel member of the choloylglycine hydrolase family with structural and functional similarity to acid ceramidase J. Biol. Chem. 2005, 280, 11082-11092
14. Tsuboi, K.; Takezaki, N.; Ueda, N. The N -acylethanolamine-hydrolyzing acid amidase (NAAA) Chem. Biodiversity 2007, 4, 1914-1925
15. Mor, M.; Rivara, S.; Lodola, A.; Plazzi, P. V.; Tarzia, G.; Duranti, A.; Tontini, A.; Piersanti, G.; Kathuria, S.; Piomelli, D. Cyclohexylcarbamic acid 3'- or 4'-substituted biphenyl-3-yl esters as fatty acid amide hydrolase inhibitors: synthesis, quantitative structure-activity relationships, and molecular modeling studies J. Med. Chem. 2004, 47, 4998-5008
16. Kathuria, S.; Gaetani, S.; Fegley, D.; Valin-o, F.; Duranti, A.; Tontini, A.; Mor, M.; Tarzia, G.; La Rana, G.; Calignano, A.; Giustino, A.; Tattoli, M.; Palmery, M.; Cuomo, V.; Piomelli, D. Modulation of anxiety through blockade of anandamide hydrolysis Nature Med. 2003, 9, 76-81
17. Tsuboi, K.; Hilligsmann, C.; Vandevoorde, S.; Lambert, D. M.; Ueda, N. N -Cyclohexanecarbonylpentadecylamine: A selective inhibitor of the acid amidase hydrolysing N -acylethanolamines, as a tool to distinguish acid amidase from fatty acid amide hydrolase Biochem. J. 2004, 379, 99-106
18. Vandevoorde, S.; Tsuboi, K.; Ueda, N.; Jonsson, K.-O.; Fowler, C. J.; Lambert, D. M. Esters, retroesters, and a retroamide of palmitic acid: pool for the first selective inhibitors of N -palmitoylethanolamine-selective acid amidase J. Med. Chem. 2003, 46, 4373-4376
19. Saturnino, C.; Petrosino, S.; Ligresti, A.; Palladino, C.; De Martino, G.; Bisogno, T.; Di Marzo, V. Synthesis and biological evaluation of new potential inhibitors of N -acylethanolamine hydrolyzing acid amidase Bioorg. Med. Chem. Lett. 2010, 20, 1210-1213
20. Rossocha, M.; Schultz-Heienbrok, R.; von Moeller, H.; Coleman, J. P.; Saenger, W. Conjugated bile acid hydrolase is a tetrameric N-terminal thiol hydrolase with specific recognition of its cholyl but not of its tauryl product Biochemistry 2005, 44, 5739-5748
21. Zhao, L.-Y.; Tsuboi, K.; Okamoto, Y.; Nagahata, S.; Ueda, N. Proteolytic activation and glycosylation of N -acylethanolamine-hydrolyzing acid amidase, a lysosomal enzyme involved in the endocannabinoid metabolism Biochim. Biophys. Acta 2007, 1771, 1397-1405
22. Wang, J.; Zhao, L.-Y.; Uyama, T.; Tsuboi, K.; Tonai, T.; Ueda, N. Amino acid residues crucial in pH regulation and proteolytic activation of N -acylethanolamine-hydrolyzing acid amidase Biochim. Biophys. Acta 2008, 1781, 710-717
23. Solorzano, C.; Zhu, C.; Battista, N.; Astarita, G.; Lodola, A.; Rivara, S.; Mor, M.; Russo, R.; Maccarrone, M.; Antonietti, F.; Duranti, A.; Tontini, A.; Cuzzocrea, S.; Tarzia, G.; Piomelli, D. Selective N -acylethanolamine- hydrolyzing acid amidase inhibition reveals a key role for endogenous palmitoylethanolamide in inflammation Proc. Natl. Acad. Sci. U.S.A. 2009, 106, 20966-20971
24. Mayer, R. J.; Louis-Flamberg, P.; Elliott, J. D.; Fisher, M.; Leber, J. Inhibition of 3-hydroxy-3-methylglutaryl coenzyme A synthase by antibiotic 1233A and other β-lactones Biochem. Biophys. Res. Commun. 1990, 169, 610-616
25. Chauhan, D.; Hideshima, T.; Anderson, K. C. A novel proteasome inhibitor NPI-0052 as an anticancer therapy Br. J. Cancer 2006, 95, 961-965 (Pubitemid 44606819)
26. Lall, M. S.; Ramtohul, Y. K.; James, M. N. G.; Vederas, J. C. Serine and threonine β-lactones: A new class of hepatitis A virus 3C cysteine proteinase inhibitors J. Org. Chem. 2002, 67, 1536-1547
27. Arnold, L. D.; Kalantar, T. H.; Vederas, J. C. Conversion of serine to stereochemically pure β-substituted a-amino acids via β-lactones J. Am. Chem. Soc. 1985, 107, 7105-7109
28. Arnold, L. D.; May, R. G.; Vederas, J. C. Synthesis of optically pure a-amino acids via salts of a-amino-β-propiolactone J. Am. Chem. Soc. 1988, 110, 2237-2241
29. Marinez, E. R.; Salmassian, E. K.; Lau, T. T.; Gutierrez, C. G. Enterobactin and enantioenterobactin J. Org. Chem. 1996, 61, 3548-3550
30. Sliedregt, K. M.; Schouten, A.; Kroon, J.; Liskamp, R. M. J. Reaction of N -trityl amino acids with BOP: efficient synthesis of t -butyl esters as well as N -trytil serine- and threonine-β-lactones Tetrahedron Lett. 1996, 37, 4237-4240
31. Parker, W. L.; Rathnum, M. L.; Liu, W.-C. SQ 26,517 - A β-lactone produced by a Bacillus species J. Antibiot. 1982, 35, 900-902
32. Montalbetti, C. A. G. N.; Falque, V. Amide bond formation and peptide coupling Tetrahedron 2005, 61, 10827-10852
33. White, A. J.; Wharton, C. W. Hydrogen-bonding in enzyme catalysis. Fourier-transform infrared detection of ground-state electronic strain in acyl-chymotrypsins and analysis of the kinetic consequences Biochem. J. 1990, 270, 627-637
34. Geske, G. D.; O'Neill, J. C.; Miller, D. M.; Mattmann, M. E.; Blackwell, H. E. Modulation of bacterial quorum sensing with synthetic ligands: systematic evaluation of N -acylated homoserine lactones in multiple species and new insights into their mechanism of action J. Am. Chem. Soc. 2007, 129, 13613-13625
35. Hutchinson, A. Note on the reduction of aromatic amides J. Chem. Soc., Trans. 1890, 57, 957
36. Bessodes, M.; Saiah, M.; Antonakis, K. A new, versatile and stereospecific route to unusual amino acids: the enantiospecific total synthesis of statine amide and its three stereoisomers J. Org. Chem. 1992, 57, 4441-4444
37. Hofmann, K.; Schmiechen, R.; Wells, R. D.; Wolman, Y.; Yanaihara, N. Studies on Polypeptides. XXIX. Synthetic peptides related to the N-terminus of bovine pancreatic ribonuclease A (Position 1-7) J. Am. Chem. Soc. 1965, 87, 611-619
38. Miller, M. J.; Mattingly, P. G.; Morrison, M. A.; Kerwin, J. F., Jr. Synthesis of β-lactams from substituted hydroxamic acids J. Am. Chem. Soc. 1980, 102, 7026-7032
39. Cohen, S. B.; Halcomb, R. L. Application of serine- and threonine-derived cyclic sulfamidates for the preparation of S -linked glycosyl amino acids in solution- and solid-phase peptide synthesis J. Am. Chem. Soc. 2002, 124, 2534-2543
40. Higashibayashi, S.; Kohno, M.; Goto, T.; Suzuki, K.; Mori, T.; Hashimoto, K.; Nakata, M. Synthetic studies on thiostrepton family of peptide antibiotics: synthesis of the pentapeptide segment containing dihydroxyisoleucine, thiazoline and dehydroamino acid Tetrahedron Lett. 2004, 45, 3707-3712
41. Pu, Y.; Martin, F. M.; Vederas, J. C. Synthesis and acylation of salts of L -threonine β-lactone: A route to β-lactone antibiotics J. Org. Chem. 1991, 56, 1280-1283
42. Sakai, N.; Ageishi, S.; Isobe, H.; Hayashi, Y.; Yamamoto, Y. Lipase promoted asymmetric trans -esterification of 4-alkyl-, 3-alkyl- and 3,4-dialkyloxetan-2-ones with ring-opening J. Chem. Soc., Perkin Trans. 1 2000, 71-77
43. Park, D. J.; Kim, D. H. Cysteine derivatives as inhibitors for carboxypeptidase A: synthesis and structure-activity relationships J. Med. Chem. 2002, 45, 911-918
44. Gomberg, M.; Pernert, J. C. Methylbiphenyls J. Am. Chem. Soc. 1926, 48, 1372-1384
45. Xiao, Z.-Y.; Zhao, X.; Jiang, X.-K.; Li, Z.-T. Self-assembly of porphyrin-azulene-porphyrin and porphyrin-azulene-conjugates Org. Biomol. Chem. 2009, 7, 2540-2547
46. Fraser, R. T. M.; Taube, H. Activation effects and rates of electron transfer J. Am. Chem. Soc. 1961, 83, 2242-2246
47. Deng, Y.; Gong, L.; Mi, A.; Liu, H.; Jiang, Y. Suzuki coupling catalyzed by ligand-free palladium(II) species at room temperature and by exposure to air Synthesis 2003, 337-339
48. 2A adenosine receptor antagonists Eur. J. Med. Chem. 1997, 32, 709-719
49. Orton, K. J. P.; Soper, F. G.; Wiliams, G. The chlorination of anilides. Part III. N -Chlorination and C -chlorination as simultaneous side reactions J. Chem. Soc. 1928, 998-1005
50. Cativiela, C.; Serrano, J. L.; Zurbano, M. M. Synthesis of 3-substituted pentane-2,4-diones: valuable intermediates for liquid crystals J. Org. Chem. 1995, 60, 3074-3083
51. Yin, J.; Bergmann, E. M.; Cherney, M. M.; Lall, M. S.; Jain, R. P.; Vederas, J. C.; James, M. N. G. Dual modes of modification of hepatitis A virus 3C protease by a serine-derived β-lactone: selective crystallization and formation of a functional catalytic triad in the active site J. Mol. Biol. 2005, 354, 854-871
52. Tomoda, H.; Ohbayashi, N.; Morikawa, Y.; Kumagai, H.; Omura, S. Binding site for fungal β-lactone hymeglusin on cytosolic 3-hydroxy-3- methylglutaryl coenzyme A synthase Biochim. Biophys. Acta 2004, 1636, 22-28
53. Greenspan, M. D.; Bull, H. G.; Yudkovitz, J. B.; Hanf, D. P.; Alberts, A. W. Inhibition of 3-hydroxy-3-methylglutaryl-CoA synthase and cholesterol biosynthesis by β-lactone inhibitors and binding of these inhibitors to the enzyme Biochem. J. 1993, 289, 889-895
54. Pojer, F.; Ferrer, J. L.; Richard, S. B.; Nagegowda, D. A.; Chye, M.-L.; Bach, T. J.; Noel, J. P. Structural basis for the design of potent and species-specific inhibitors of 3-hydroxy-3-methylglutaryl CoA synthases Proc. Natl. Acad. Sci. U.S.A. 2006, 103, 11491-11496
55. ACD/LogP, version 8.00; Advanced Chemistry Development, Inc.: Toronto ON, Canada, 2004; www.acdlabs.com.
56. Oliver, C. M.; Schaefer, A. M.; Greenberg, E. P.; Sufrin, J. R. Microvawe synthesis and evaluation of phenacylhomoserine lactones as anticancer compounds that minimally activate quorum sensing pathways in Pseudomonas aeruginosa J. Med. Chem. 2009, 52, 1569-1575
57. Lu, X.; Lin, S. Pd(II)-Bipyridine catalyzed conjugate addition of arylboronic acid to a,β-unsaturated carbonyl compounds J. Org. Chem. 2005, 70, 9651-9653
58. Wang, Z.; Gu, C.; Colby, T.; Shindo, T.; Balamurugan, R.; Waldmann, H.; Kaiser, M.; van der Hoorn, R. A. L. β-Lactone probes identify a papain-like peptide ligase in Arabidopsis thaliana Nat. Chem. Biol. 2008, 4, 557-563
59. 2-catalyzed Suzuki coupling reactions of aryl bromides under mild aerobic conditions J. Org. Chem. 2004, 69, 4330-4335
60. Tzschucke, C. C.; Bannwart, W. Fluorous-silica-supported perfluoro-tagged palladium complexes catalyze Suzuki couplings in water Helv. Chim. Acta 2004, 87, 2882-2889
61. Chase, B. H. Ester exchange in the hydrolysis of diphenyl terephthalate J. Chem. Soc. 1963, 1334-1335
62. 5 system: β-fragmentation versus O -neophyl rearrangement Eur. J. Inorg. Chem. 1999, 9, 1467-1477
63. Sali, A.; Blundell, T. L. Comparative protein modelling by satisfaction of spatial restraints J. Mol. Biol. 1993, 234, 779-815
64. Halgren, T. A.; MMFF, V. I. MMFF94s option for energy minimization studies J. Comput. Chem. 1999, 20, 720-729
65. Macromodel version 8.5; Schrödinger LLC: New York, 2008.
66. Maestro, version 8.5; Schrödinger, LLC: New York, 2008.
67. Friesner, R. A.; Banks, J. L.; Murphy, R. B.; Halgren, T. A.; Klicic, J. J.; Mainz, D. T.; Repasky, M. P.; Knoll, E. H.; Shelley, M.; Perry, J. K.; Shaw, D. E.; Francis, P.; Shenkin, P. S. Glide: A new approach for rapid, accurate docking and scoring. 1. Method and assessment of docking accuracy J. Med. Chem. 2004, 47, 1739-1749