Modulation of cAMP-specific PDE without emetogenic activity: New sulfide-like PDE7 inhibitors

Journal of Medicinal Chemistry

Volumn 57, Issue 20, 2014, Pages 8590-8607

  García, Ana M ^a   Brea, José ^b   Morales García, Jose A ^c,d   Perez, Daniel I ^a   González, Alejandro ^b   Alonso Gil, Sandra ^c,d   Gracia Rubio, Irene ^e   Ros Simó, Clara ^e   Conde, Santiago ^f   Cadavid, María Isabel ^b   Loza, María Isabel ^b   Perez Castillo, Ana ^c,d   Valverde, Olga ^e   Martinez, Ana ^a   Gil, Carmen ^a  

^a CENTRO DE INVESTIGACIONES BIOLÓGICAS   (Spain)

^b UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

^c INSTITUTO DE INVESTIGACIONES BIOMÉDICAS ALBERTO SOLS   (Spain)

^d CENTRO DE INVESTIGACIÓN BIOMÉDICA EN RED SOBRE ENFERMEDADES NEURODEGENERATIVAS CIBERNED   (Spain)

^e INST MUNIC D INVESTIGACIO MEDICA   (Spain)

^f INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 BROMOPHENYL 4 CHLORO 2 NITROPHENYL SULFIDE; 2 BROMOPHENYL 5 CHLORO 2 NITROPHENYL SULFIDE; 2 METHYL 5 NITROBENZENESULFONIC ACID DIMETHYLAMIDE; 2 [(2 CHLORO 4 NITROPHENYL)THIO]PYRIDINE; 4 (3 CHLORO 4 NITROPHENYLTHIO)ANILINE; 4 (4 CHLORO 2 NITROPHENYLTHIO)ANILINE; 4 CHLORO 2 NITROPHENYL PHENYL SULFIDE; 4 [(2 CHLORO 4 NITROPHENYL)THIO]PYRIDINE; 4 [(4 CHLORO 4 NITROPHENYL)THIO]PYRIDINE; CYCLIC AMP; DIPHENYL SULFIDE DERIVATIVE; PHOSPHODIESTERASE VII INHIBITOR; QUINAZOLINE; ROLIPRAM; SULFIDE; UNCLASSIFIED DRUG; NONSTEROID ANTIINFLAMMATORY AGENT; PDE7A PROTEIN, HUMAN; PHOSPHODIESTERASE INHIBITOR; PHOSPHODIESTERASE VII;

ANIMAL CELL; ANIMAL EXPERIMENT; ANIMAL MODEL; ANIMAL TISSUE; ARTICLE; BIOLOGICAL ACTIVITY; BLOOD BRAIN BARRIER; CELL VIABILITY; CONTROLLED STUDY; HUMAN; HUMAN CELL; IC50; MALE; MOUSE; NONHUMAN; PARKINSON DISEASE; RAT; VOMITING; ADVERSE EFFECTS; ANESTHESIA; ANIMAL; ANTAGONISTS AND INHIBITORS; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMICALLY INDUCED; CHEMISTRY; DRUG EFFECTS; DRUG SCREENING; INBRED MOUSE STRAIN; PROCEDURES; STRUCTURE ACTIVITY RELATION; SYNTHESIS;

ANESTHESIA; ANIMALS; ANTI-INFLAMMATORY AGENTS, NON-STEROIDAL; BLOOD-BRAIN BARRIER; CELL SURVIVAL; CHEMISTRY TECHNIQUES, SYNTHETIC; CYCLIC NUCLEOTIDE PHOSPHODIESTERASES, TYPE 7; DRUG EVALUATION, PRECLINICAL; HUMANS; INHIBITORY CONCENTRATION 50; MALE; MICE, INBRED STRAINS; MODELS, MOLECULAR; PHOSPHODIESTERASE INHIBITORS; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; SULFIDES; VOMITING;

EID: 84908377043     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm501090m     Document Type: Article

References (41)

1. Schneider, S. A.; Obeso, J. A. Movement disorders: improved understanding of early disease Lancet Neurol. 2013, 12, 10-12
2. Ferrer, I.; Lopez-Gonzalez, I.; Carmona, M.; Dalfo, E.; Pujol, A.; Martinez, A. Neurochemistry and the non-motor aspects of PD Neurobiol. Dis. 2012, 46, 508-526
3. Baumann, C. R. Epidemiology, diagnosis and differential diagnosis in Parkinson's disease tremor Parkinsonism Relat. Disord. 2012, 18 (Suppl 1) S90-S92
4. Jennum, P.; Zoetmulder, M.; Korbo, L.; Kjellberg, J. The health-related, social, and economic consequences of parkinsonism: a controlled national study J. Neurol. 2011, 258, 1497-1506
5. Wirdefeldt, K.; Adami, H. O.; Cole, P.; Trichopoulos, D.; Mandel, J. Epidemiology and etiology of Parkinson's disease: a review of the evidence Eur. J. Epidemiol. 2011, 26 (Suppl 1) S1-S58
6. Lotharius, J.; Brundin, P. Pathogenesis of Parkinson's disease: dopamine, vesicles and alpha-synuclein Nature Rev. Neurosci. 2002, 3, 932-942
7. Weiner, W. J. The initial treatment of Parkinson's disease should begin with levodopa Movement Disord. 1999, 14, 716-724
8. Vidailhet, M.; Bonnet, A. M.; Marconi, R.; Durif, F.; Agid, Y. The phenomenology of l -dopa-induced dyskinesias in Parkinson's disease Movement Disord. 1999, 14 (Suppl 1) 13-18
9. Poewe, W.; Mahlknecht, P.; Jankovic, J. Emerging therapies for Parkinson's disease Curr. Opin. Neurol. 2012, 25, 448-459
10. Gil, C.; Campillo, N. E.; Perez, D. I.; Martinez, A. Phosphodiesterase 7 (PDE7) inhibitors as new drugs for neurological and inflammatory disorders Expert Opin. Ther. Pat. 2008, 18, 1127-1139
11. Castro, A.; Jerez, M. J.; Gil, C.; Calderon, F.; Domenech, T.; Nueda, A.; Martinez, A. CODES, a novel procedure for ligand-based virtual screening: PDE7 inhibitors as an application example Eur. J. Med. Chem. 2008, 43, 1349-1359
12. Morales-Garcia, J. A.; Redondo, M.; Alonso-Gil, S.; Gil, C.; Perez, C.; Martinez, A.; Santos, A.; Perez-Castillo, A. Phosphodiesterase 7 inhibition preserves dopaminergic neurons in cellular and rodent models of Parkinson disease PLoS One 2011, 6, e17240
13. Martinez, A.; Gil, C., Phosphodiesterase inhibitors as new therapeutic approach for the treatment of Parkinson's disease. In Emerging Drugs and Targets for Parkinson's Disease; Martinez, A.; Gil, C., Eds.; Royal Society of Chemistry: Cambridge, UK, 2013; pp 294-307.
14. Morales-Garcia, J. A.; Susin, C.; Alonso-Gil, S.; Perez, D. I.; Palomo, V.; Perez, C.; Conde, S.; Santos, A.; Gil, C.; Martinez, A.; Perez-Castillo, A. Glycogen synthase kinase-3 inhibitors as potent therapeutic agents for the treatment of Parkinson disease ACS Chem. Neurosci. 2013, 4, 350-360
15. Robichaud, A.; Savoie, C.; Stamatiou, P. B.; Lachance, N.; Jolicoeur, P.; Rasori, R.; Chan, C. C. Assessing the emetic potential of PDE4 inhibitors in rats Br. J. Pharmacol. 2002, 135, 113-118
16. Fried, K. W.; Schneider, C. M.; Schramm, K. W.; Datta, A.; Chahbane, N.; Corsten, C.; Powell, D. R.; Lenoir, D.; Kettrup, A.; Terranova, P.; Georg, G. I.; Rozman, K. K. From dioxin to drug lead - the development of 2,3,7,8-tetrachlorophenothiazine ChemMedChem 2007, 2, 890-897
17. Rathore, B. S.; Gupta, V.; Gupta, R. R.; Kumar, M. Synthesis of 7-chloro-9-trifluoromethyl-/7-fluorophenothiazines Heteroatom. Chem. 2007, 18, 81-86
18. Movsesian, M. A.; Kukreja, R. C. Phosphodiesterase inhibition in heart failure Handb. Exp. Pharmacol. 2011, 237-249
19. Robichaud, A.; Stamatiou, P. B.; Jin, S. L.; Lachance, N.; MacDonald, D.; Laliberte, F.; Liu, S.; Huang, Z.; Conti, M.; Chan, C. C. Deletion of phosphodiesterase 4D in mice shortens alpha(2)-adrenoceptor-mediated anesthesia, a behavioral correlate of emesis J. Clin. Invest. 2002, 110, 1045-1052
20. Smith, S. J.; Cieslinski, L. B.; Newton, R.; Donnelly, L. E.; Fenwick, P. S.; Nicholson, A. G.; Barnes, P. J.; Barnette, M. S.; Giembycz, M. A. Discovery of BRL 50481 [3-(N, N -dimethylsulfonamido)-4-methyl-nitrobenzene], a selective inhibitor of phosphodiesterase 7: in vitro studies in human monocytes, lung macrophages, and CD8+ T-lymphocytes Mol. Pharmacol. 2004, 66, 1679-1689
21. Di, L.; Kerns, E. H.; Carter, G. T. Strategies to assess blood-brain barrier penetration Expert Opin. Drug Discovery 2008, 3, 677-687
22. Di, L.; Kerns, E. H.; Fan, K.; McConnell, O. J.; Carter, G. T. High throughput artificial membrane permeability assay for blood-brain barrier Eur. J. Med. Chem. 2003, 38, 223-232
23. Crivori, P.; Cruciani, G.; Carrupt, P. A.; Testa, B. Predicting blood-brain barrier permeation from three-dimensional molecular structure J. Med. Chem. 2000, 43, 2204-2216
24. Mori, F.; Perez-Torres, S.; De Caro, R.; Porzionato, A.; Macchi, V.; Beleta, J.; Gavalda, A.; Palacios, J. M.; Mengod, G. The human area postrema and other nuclei related to the emetic reflex express cAMP phosphodiesterases 4B and 4D J. Chem. Neuroanat. 2010, 40, 36-42
25. Page, C. P.; Spina, D. Phosphodiesterase inhibitors in the treatment of inflammatory diseases Handb. Exp. Pharmacol. 2011, 391-414
26. Castaño, T.; Wang, H.; Campillo, N. E.; Ballester, S.; Gonzalez-Garcia, C.; Hernandez, J.; Perez, C.; Cuenca, J.; Perez-Castillo, A.; Martinez, A.; Huertas, O.; Gelpi, J. L.; Luque, F. J.; Ke, H.; Gil, C. Synthesis, Structural Analysis, and Biological Evaluation of Thioxoquinazoline Derivatives as Phosphodiesterase 7 Inhibitors ChemMedChem 2009, 4, 866-876
27. Redondo, M.; Brea, J.; Perez, D. I.; Soteras, I.; Val, C.; Perez, C.; Morales-Garcia, J. A.; Alonso-Gil, S.; Paul-Fernandez, N.; Martin-Alvarez, R.; Cadavid, M. I.; Loza, M. I.; Perez-Castillo, A.; Mengod, G.; Campillo, N. E.; Martinez, A.; Gil, C. Effect of phosphodiesterase 7 (PDE7) inhibitors in experimental autoimmune encephalomyelitis mice. Discovery of a new chemically diverse family of compounds J. Med. Chem. 2012, 55, 3274-3284
28. Redondo, M.; Palomo, V.; Brea, J.; Perez, D. I.; Martin-Alvarez, R.; Perez, C.; Paul-Fernandez, N.; Conde, S.; Cadavid, M. I.; Loza, M. I.; Mengod, G.; Martinez, A.; Gil, C.; Campillo, N. E. Identification in silico and experimental validation of novel phosphodiesterase 7 inhibitors with efficacy in experimental autoimmune encephalomyelitis mice ACS Chem. Neurosci. 2012, 3, 793-803
29. Roe, A.; Little, W. F. The preparation of some fluorophenothiazine and trifluoromethylphenothiazine, and some observations regardind determination of their structure by infrared spectroscopy J. Org. Chem. 1955, 20, 1577-1590
30. Youssef, M. S. K.; Elezbawy, S. R.; Abdelwahab, A. A. Synthesis of new 4- N -thienylidenamino and 4- N -furfurylideneamino diaryl sulfides and sulfones Acta Pharm. Jugosl. 1981, 31, 67-70
31. Breitenstein, W.; Marki, F.; Roggo, S.; Wiesenberg, I.; Pfeilschifter, J.; Furet, P.; Beriger, E. A new class of inhibitors of secretory phospholipase A(2)-enolized 1,3-dioxane-4,6-dione-5-carboxamides Eur. J. Med. Chem. 1994, 29, 649-658
32. Galbreath, R. J.; Ingham, R. K. Synthesis of 2-chlorophenothiazine via a smiles rearrangement J. Org. Chem. 1958, 23, 1804-1806
33. Sharma, H. L.; Sharma, V. N.; Mital, R. L. Studies on synthesis of nitrophenothiazines by smiles rearrangement behaviour of halonitrobenzenes with o -aminothiophenol Tetrahedron Lett. 1967, 1657-1662
34. Girault, S.; Baillet, S.; Horvath, D.; Lucas, V.; Davioud-Charvet, E.; Tartar, A.; Sergheraert, C. New potent inhibitors of trypanothione reductase from Trypanosoma cruzi in the 2-aminodiphenylsulfide series Eur. J. Med. Chem. 1997, 32, 39-52
35. Stump, B.; Eberle, C.; Kaiser, M.; Brun, R.; Krauth-Siegel, R. L.; Diederich, F. Diaryl sulfide-based inhibitors of trypanothione reductase: inhibition potency, revised binding mode and antiprotozoal activities Org. Biomol. Chem. 2008, 6, 3935-3947
36. Moore, M. L.; Johnson, T. B. The molecular rearrangement of sulfenanilides III J. Am. Chem. Soc. 1936, 58, 1091-1094
37. de la Cruz, A.; Elguero, J.; Goya, P.; Martinez, A. Synthesis and antimicrobial evaluation of new derivatives of diphenylsulfone Boll. Chim. Farm. 1994, 133, 72-75
38. Berg, S. S. Nuclear-substituted derivatives of 4-4′-diaminodiphenyl Sulphone J. Chem. Soc. 1949, 1991-1993
39. Bunnett, J. F.; Davis, G. T. Kinetics of reactions of 2,4-dinitrochlorobenzene with some familiar nucleophilic reagents J. Am. Chem. Soc. 1954, 76, 3011-3015
40. Jones, T. R.; Webber, S. E.; Varney, M. D.; Reddy, M. R.; Lewis, K. K.; Kathardekar, V.; Mazdiyasni, H.; Deal, J.; Nguyen, D.; Welsh, K. M.; Webber, S.; Johnston, A.; Matthews, D. A.; Smith, W. W.; Janson, C. A.; Bacquet, R. J.; Howland, E. F.; Booth, C. L. J.; Herrmann, S. M.; Ward, R. W.; White, J.; Bartlett, C. A.; Morse, C. A. Structure-based design of substituted diphenyl sulfones and sulfoxides as lipophilic inhibitors of thymidylate synthase J. Med. Chem. 1997, 40, 677-683
41. Luna-Medina, R.; Cortes-Canteli, M.; Alonso, M.; Santos, A.; Martinez, A.; Perez-Castillo, A. Regulation of inflammatory response in neural cells in vitro by thiadiazolidinones derivatives through peroxisome proliferator-activated receptor gamma activation J. Biol. Chem. 2005, 280, 21453-21462