Dibenzo[1,4,5]thiadiazepine: A hardly-known heterocyclic system with neuroprotective properties of potential usefulness in the treatment of neurodegenerative diseases

European Journal of Medicinal Chemistry

Volumn 81, Issue , 2014, Pages 350-358

  González Muñoz, Gema C ^a   Arce, Mariana P ^a   Pérez, Concepción ^a   Romero, Alejandro ^b   Villarroya, Mercedes ^b   López, Manuela G ^b   Conde, Santiago ^a   Rodríguez Franco, María Isabel ^a  

^a INSTITUTO DE QUÍMICA MÉDICA   (Spain)

^b UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

Alzheimer's disease; Antioxidant; Calcium modulation; Dibenzo 1,4,5 thiadiazepines; Mitochondrial oxidative stress; Neuroprotection

Indexed keywords

2 CHLORO 5,6 DIHYDRO 5,6 DIACETYLDIBENZO[B,F][1,4,5]THIADIAZEPINE; 2 FLUOROMETHYL 5,6 DIHYDRO 5,6 DIACETYLDIBENZO[B,F][1,4,5]THIADIAZEPINE; 2 METHOXY 5,6 DIHYDRO 5,6 DIACETYLDIBENZO[B,F][1,4,5] THIADIAZEPINE; 2 NITRO 5,6 DIHYDRO 6 ACETYLDIBENZO[B,F][1,4,5]THIADIAZEPINE; 3 CHLORO 5,6 DIHYDRO 5,6 DI(2 DIMETHYLAMINO) PROPIONYLDIBENZO[B,F][1,4,5]THIADIAZEPINE; 3 CHLORO 5,6 DIHYDRO 5,6 DI(4 METHYLPIPERAZIN 1 YL) ACETYLDIBENZO[B,F][1,4,5]THIADIAZEPINE; 3 CHLORO 5,6 DIHYDRO 5,6 DIACETYLDIBENZO[B,F][1,4,5]THIADIAZEPINE; 3 CHLORO 5,6 DIHYDRO 5,6 DI[2 (PIPERIDIN 1 YL)] PROPIONYLDIBENZO[B,F][1,4,5]THIADIAZEPINE; 3 CHLORO 5,6 DIHYDRO 5,6 DI[2 (PIRROLIDIN 1 YL)] PROPIONYLDIBENZO[B,F][1,4,5]THIADIAZEPINE; 3 CHLORODIBENZO[B,F][1,4,5]THIADIAZEPINE; 4 CHLORO 5,6 DIHYDRO 5,6 DI(PIPERIDIN 1 YL)ACETYLDIBENZO [B,F][1,4,5]THIADIAZEPINE; ANTIOXIDANT; DIBENZO[1,4,5]THIADIAZEPINE; HYDRAZIDES,N,N DIACYLHYDRAZINE; N [2 (2,4 DINITROTHIOPHENYL)PHENYL] N,N' DIACETYLHYDRAZINE; N [2 (4 METHOXY 2 NITROTHIOPHENYL)PHENYL] N,N' DIACETYLHYDRAZINE; N [2 (4 TRIFLUOROMETHYL 2 NITROTHIOPHENYL)PHENYL] N,N' DIACETYLHYDRAZINE; N [2 (5 CHLOR 2 NITROTHIOPHENYL)PHENYL] N,N' DI(2 BROMOPROPIONYL)HYDRAZINE; N [2 (5 CHLOR 2 NITROTHIOPHENYL)PHENYL] N,N' DI(2 DIMETHYLAMINOPROPIONYL)HYDRAZINE; N [2 (5 CHLOR 2 NITROTHIOPHENYL)PHENYL] N,N' DI[(2 DIPIPERIDIN 1 YL)PROPIONYL]HYDRAZINE; N [2 (5 CHLOR 2 NITROTHIOPHENYL)PHENYL] N,N' DI[(2 DIPIRROLIDIN 1 YL)PROPIONYL]HYDRAZINE; N [2 (5 CHLORO 2 NITROTHIOPHENYL)PHENYL] N,N' BIS(4 METHYLPIPERAZIN 1 YL)DIACETYLHYRAZINE; N [2 (6 CHLORO 2 NITROTHIOPHENYL)PHENYL] N,N' BIS(PIPERIDIN 1 YL)DIACETYLHYDRAZINE; NEUROPROTECTIVE AGENT; NIFEDIPINE; UNCLASSIFIED DRUG; DIBENZO(1,4,5)THIADIAZEPINE; REACTIVE OXYGEN METABOLITE; THIAZEPINE DERIVATIVE;

ANTIOXIDANT ACTIVITY; ARTICLE; BLOOD BRAIN BARRIER; CALCIUM HOMEOSTASIS; CARBON NUCLEAR MAGNETIC RESONANCE; CELL VIABILITY; CONTROLLED STUDY; DEGENERATIVE DISEASE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; INTRACELLULAR SIGNALING; NEUROBLASTOMA CELL LINE; NEUROPROTECTION; OXIDATIVE STRESS; PROTON NUCLEAR MAGNETIC RESONANCE; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECTS; METABOLISM; MITOCHONDRION; NEURODEGENERATIVE DISEASES; SYNTHESIS; TUMOR CELL LINE;

ANTIOXIDANTS; CELL LINE, TUMOR; CELL SURVIVAL; HUMANS; MITOCHONDRIA; MOLECULAR STRUCTURE; NEURODEGENERATIVE DISEASES; NEUROPROTECTIVE AGENTS; OXIDATIVE STRESS; REACTIVE OXYGEN SPECIES; THIAZEPINES;

EID: 84901256513     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2014.04.075     Document Type: Article

References (37)

1. Alzheimer's Association Alzheimer's Disease Facts and Figures 2013 http://www.alz.org/downloads/facts-figures-2013.pdf
2. F.A. Luque, and S.L. Jaffe The molecular and cellular pathogenesis of dementia of the Alzheimer's type an overview Int. Rev. Neurobiol. 84 2009 151 165
3. T.S. Anekonda, and J.F. Quinn Calcium channel blocking as a therapeutic strategy for Alzheimer's disease: the case for isradipine Biochim. Biophys. Acta 1812 2011 1584 1590
4. M. Dumont, and M.F. Beal Neuroprotective strategies involving ROS in Alzheimer disease Free Radic. Biol. Med. 51 2011 1014 1026
5. S. Benfeito, C. Oliveira, P. Soares, C. Fernandes, T. Silva, J. Teixeira, and F. Borges Antioxidant therapy: still in search of the 'magic bullet' Mitochondrion 13 2013 427 435
6. G.E. Stutzmann Calcium dysregulation, IP3 signaling, and Alzheimer's disease Neuroscientist 11 2005 110 115 (Pubitemid 40388493)
7. V. Pogačić Kramp List of drugs in development for neurodegenerative diseases: update October 2011 Neurodegener. Dis. 9 2012 210 283
8. R. Morphy, and Z. Rankovic Designed multiple ligands. An emerging drug discovery paradigm J. Med. Chem. 48 2005 6523 6543 (Pubitemid 41504710)
9. M.L. Bolognesi, E. Simoni, M. Rosini, A. Minarini, V. Tumiatti, and C. Melchiorre Multitarget-directed ligands: innovative chemical probes and therapeutic tools against Alzheimer's disease Curr. Top. Med. Chem. 11 2011 2797 2806
10. A. Cavalli, M.L. Bolognesi, S. Capsoni, V. Andrisano, M. Bartolini, E. Margotti, A. Cattaneo, M. Recanatini, and C. Melchiorre A small molecule targeting the multifactorial nature of Alzheimer's disease Angew. Chem. Int. Ed. Engl. 46 2007 3689 3692 (Pubitemid 46981250)
11. M.I. Fernández-Bachiller, C. Pérez, L. Monjas, J. Rademann, and M.I. Rodríguez-Franco New tacrine-4-oxo-4H-chromene hybrids as multifunctional agents for the treatment of Alzheimer's disease, with cholinergic, antioxidant, and beta-amyloid-reducing properties J. Med. Chem. 55 2012 1303 1317
12. M. Maroto, A.M. de Diego, E. Albinana, J.C. Fernández-Morales, A. Caricati-Neto, A. Jurkiewicz, M. Yáñez, M.I. Rodríguez- Franco, S. Conde, M.P. Arce, J.M. Hernández-Guijo, and A.G. García Multi-target novel neuroprotective compound ITH33/IQM9.21 inhibits calcium entry, calcium signals and exocytosis Cell. Calcium 50 2011 359 369
13. M.I. Fernández-Bachiller, C. Pérez, G.C. González-Muñoz, S. Conde, M.G. López, M. Villarroya, A.G. García, and M.I. Rodríguez-Franco Novel tacrine-8-hydroxyquinoline hybrids as multifunctional agents for the treatment of Alzheimer's disease, with neuroprotective, cholinergic, antioxidant, and copper-complexing properties J. Med. Chem. 53 2010 4927 4937
14. M.P. Arce, M.I. Rodríguez-Franco, G.C. González- Muñoz, C. Pérez, B. López, M. Villarroya, M.G. López, A.G. García, and S. Conde Neuroprotective and cholinergic properties of multifunctional glutamic acid derivatives for the treatment of Alzheimer's disease J. Med. Chem. 52 2009 7249 7257
15. M.I. Fernández-Bachiller, C. Pérez, N.E. Campillo, J.A. Páez, G.C. González-Muñoz, P. Usán, E. García-Palomero, M.G. López, M. Villarroya, A.G. García, A. Martínez, and M.I. Rodríguez-Franco Tacrine-melatonin hybrids as multifunctional agents for Alzheimer's disease, with cholinergic, antioxidant, and neuroprotective properties ChemMedChem 4 2009 828 841
16. M.I. Rodríguez-Franco, M.I. Fernández-Bachiller, C. Pérez, B. Hernández-Ledesma, and B. Bartolomé Novel tacrine-melatonin hybrids as dual-acting drugs for Alzheimer disease, with improved acetylcholinesterase inhibitory and antioxidant properties J. Med. Chem. 49 2006 459 462 (Pubitemid 43157478)
17. C. Spuch, D. Antequera, M.I. Fernández-Bachiller, M.I. Rodríguez-Franco, and E. Carro A new tacrine-melatonin hybrid reduces amyloid burden and behavioral deficits in a mouse model of Alzheimer's disease Neurotox. Res. 17 2010 421 431
18. D. Antequera, M. Bolos, C. Spuch, C. Pascual, I. Ferrer, M.I. Fernández-Bachiller, M.I. Rodríguez-Franco, and E. Carro Effects of a tacrine-8-hydroxyquinoline hybrid (IQM-622) on Abeta accumulation and cell death: involvement in hippocampal neuronal loss in Alzheimer's disease Neurobiol. Dis. 46 2012 682 691
19. S. Lorrio, V. Gómez-Rangel, P. Negredo, J. Egea, R. León, A. Romero, T. Dal-Cim, M. Villarroya, M.I. Rodríguez-Franco, S. Conde, M.P. Arce, J.M. Roda, A.G. García, and M.G. López Novel multitarget ligand ITH33/IQM9.21 provides neuroprotection in in vitro and in vivo models related to brain ischemia Neuropharmacology 67 2013 403 411
20. S. Conde, D.I. Pérez, A. Martínez, C. Pérez, and F.J. Moreno Thienyl and phenyl alpha-halomethyl ketones: new inhibitors of glycogen synthase kinase (GSK-3beta) from a library of compound searching J. Med. Chem. 46 2003 4631 4633 (Pubitemid 37271611)
21. D.I. Pérez, S. Conde, C. Pérez, C. Gil, D. Simon, F. Wandosell, F.J. Moreno, J.L. Gelpi, F.J. Luque, and A. Martínez Thienylhalomethylketones: irreversible glycogen synthase kinase 3 inhibitors as useful pharmacological tools Bioorg. Med. Chem. 17 2009 6914 6925
22. J.A. Morales-García, C. Susín, S. Alonso-Gil, D.I. Pérez, V. Palomo, C. Pérez, S. Conde, A. Santos, C. Gil, A. Martínez, and A. Pérez-Castillo Glycogen synthase kinase-3 inhibitors as potent therapeutic agents for the treatment of Parkinson disease ACS Chem. Neurosci. 4 2013 350 360
23. G.C. González-Muñoz, M.P. Arce, B. López, C. Pérez, M. Villarroya, M.G. López, A.G. García, S. Conde, and M.I. Rodríguez-Franco Old phenothiazine and dibenzothiadiazepine derivatives for tomorrow's neuroprotective therapies against neurodegenerative diseases Eur. J. Med. Chem. 45 2010 6152 6158
24. G.C. González-Muñoz, M.P. Arce, B. López, C. Pérez, A. Romero, L. del Barrio, M.D. Martín-de-Saavedra, J. Egea, R. León, M. Villarroya, M.G. López, A.G. García, S. Conde, and M.I. Rodríguez-Franco N-acylaminophenothiazines: neuroprotective agents displaying multifunctional activities for a potential treatment of Alzheimer's disease Eur. J. Med. Chem. 46 2011 2224 2235
25. M.J. Ohlow, and B. Moosmann Phenothiazine: the seven lives of pharmacology's first lead structure Drug Discov. Today 16 2011 119 131
26. A.C.-Y. Chen, J.M. Scott, B.A. Stearns, N.S. Stock, Y.P. Truong, Tricyclic compounds useful as neurogenic and neuroprotective agents, PCT Int. Appl. (2013) WO2013043744.
27. C. Korth, B.C. May, F.E. Cohen, and S.B. Prusiner Acridine and phenothiazine derivatives as pharmacotherapeutics for prion disease Proc. Natl. Acad. Sci. U S A 98 2001 9836 9841 (Pubitemid 32769390)
28. C. Corral, J. Lissavetzky, and G. Quintanilla New method for the synthesis of chloro-substituted dibenzo[b,f][1,4,5]thiadiazepines and their 5,6-dihydroderivatives J. Org. Chem. 47 1982 2214 2215
29. G.L. Ellman, K.D. Courtney, V. Andres Jr., and R.M. Feather-Stone A new and rapid colorimetric determination of acetylcholinesterase activity Biochem. Pharmacol. 7 1961 88 95
30. M. Cygler, J.D. Schrag, J.L. Sussman, M. Harel, I. Silman, M.K. Gentry, and B.P. Doctor Relationship between sequence conservation and three-dimensional structure in a large family of esterases, lipases, and related proteins Protein Sci. 2 1993 366 382 (Pubitemid 23071285)
31. L. Di, E.H. Kerns, K. Fan, O.J. McConnell, and G.T. Carter High throughput artificial membrane permeability assay for blood-brain barrier Eur. J. Med. Chem. 38 2003 223 232 (Pubitemid 36349665)
32. J. Egea, A.O. Rosa, A. Cuadrado, A.G. García, and M.G. López Nicotinic receptor activation by epibatidine induces heme oxygenase-1 and protects chromaffin cells against oxidative stress J. Neurochem. 102 2007 1842 1852 (Pubitemid 47329263)
33. T. Valero, L. del Barrio, J. Egea, N. Cañas, A. Martínez, A.G. García, M. Villarroya, and M.G. López NP04634 prevents cell damage caused by calcium overload and mitochondrial disruption in bovine chromaffin cells Eur. J. Pharmacol. 607 2009 47 53
34. J. Cooper-Knock, J. Kirby, L. Ferraiuolo, P.R. Heath, M. Rattray, and P.J. Shaw Gene expression profiling in human neurodegenerative disease Nat. Rev. Neurol. 8 2012 518 530
35. P.C. Trippier, K. Jansen Labby, D.D. Hawker, J.J. Mataka, and R.B. Silverman Target- and mechanism-based therapeutics for neurodegenerative diseases: strength in numbers J. Med. Chem. 56 2013 3121 3147
36. A. Roe, and W.F. Little The preparation of some fluoro- and trifluoromethylphenothiazines, and some observations regarding determination of their structure by infrared spectroscopy J. Org. Chem. 20 1955 1577 1590
37. C.P. LeBel, H. Ischiropoulos, and S.C. Bondy Evaluation of the probe 2',7'-dichlorofluorescin as an indicator of reactive oxygen species formation and oxidative stress Chem. Res. Toxicol. 5 1992 227 231