Carbamate derivatives of indolines as cholinesterase inhibitors and antioxidants for the treatment of Alzheimer's disease

Journal of Medicinal Chemistry

Volumn 55, Issue 23, 2012, Pages 10700-10715

  Yanovsky, Inessa ^a   Finkin Groner, Efrat ^b   Zaikin, Andrey ^b   Lerman, Lena ^a   Shalom, Hila ^a   Zeeli, Shani ^a   Weill, Tehilla ^c   Ginsburg, Isaac ^c   Nudelman, Abraham ^a   Weinstock, Marta ^b  

^a BAR ILAN UNIVERSITY   (Israel)

^b HADASSAH HEBREW UNIVERSITY MEDICAL CENTER   (Israel)

^c HEBREW UNIVERSITY OF JERUSALEM   (Israel)

Author keywords

[No Author keywords available]

Indexed keywords

3 (2 AMINOETHYL)INDOLIN 4 YLETHYL(METHYL)CARBAMATE; 3 (3 AMINO 3 OXOPROPYL)INDOLIN 4 YL ETHYL(METHYL)CARBAMATE; 3 (3 METHOXY 3 OXOPROPYL) 4 [[(4 METHOXYPHENYL)(METHYL)CARBAMOYL]OXY]INDOLIN 1 IUM; 3 (3 OXOBUTYL)INDOLIN 4 YL ETHYL(METHYL)CARBAMATE; 3 [2 (METHOXYCARBONYL)ETHYL] 1 INDOLINE 6 YL BUTYL(METHYL)CARBAMATE; 3 [2 (METHOXYCARBONYL)ETHYL] 1 INDOLINE 6 YL ETHYL(METHYL)CARBAMATE; 3 [2 (METHOXYCARBONYL)ETHYL] 1 METHYL 1H INDOL 4 YL ETHYL(METHYL)CARBAMATE; 3 [2 (METHOXYCARBONYL)ETHYL] 1 METHYLINDOLIN 4 YL 4 METHOXYPHENYL(METHYL)CARBAMATE; 3 [2 (METHOXYCARBONYL)ETHYL] 1 METHYLINDOLIN 4 YL BUTYL(METHYL)CARBAMATE; 3 [2 (METHOXYCARBONYL)ETHYL] 1 METHYLINDOLIN 4 YL ETHYL(METHYL)CARBAMATE; 3 [2 (METHOXYCARBONYL)ETHYL] 1H INDOL 4 YL ETHYL(METHYL)CARBAMATE; 3 [2 (METHOXYCARBONYL)ETHYL]INDOLIN 4 YL ETHYL(METHYL)CARBAMATE; 3 [4 [(4 METHOXYPHENYL)(METHYL)CARBAMOYL)INDOLIN 3 YL]PROPANOIC ACID; 3 [4 [(4 METHOXYPHENYL)(METHYL)CARBONYL] 1 METHYLINDOLIN 3 YL]PROPANOIC ACID; 3 [4 [[ETHYL(METHYL)CARBAMOYL]OXY] 1 METHYLINDOLIN 3 YL) PROPANOIC ACID; 3 [6 [BUTYL(METHYL)CARBOMOYLOXY]1 METHYLINDOLIN 3 YL]PROPANOATE; 3 [6 [ETHYL(METHYL)CARBOMOYLOXY]INDOLIN 3 YL]PROPANOIC ACID; ACETYLCHOLINESTERASE; ANTIOXIDANT; BUTYLCHOLINESTERASE; CARBAMIC ACID DERIVATIVE; CHOLINESTERASE; CHOLINESTERASE INHIBITOR; ETHYL 3 [4 [ETHYL(METHYL)CARBAMOYLOXY]INDOLINIUM]CITRATE; INDOLE DERIVATIVE; INDOLIN 4 OL; INDOLINE DERIVATIVE; METHYL 3 [6[(4 METHOXYPHENYL)(METHYL)CARBAMOYLOXY) 1H INDOL 3 YL)PROPANOATE; REACTIVE NITROGEN SPECIES; REACTIVE OXYGEN METABOLITE; UNCLASSIFIED DRUG;

ALZHEIMER DISEASE; ANIMAL CELL; ANTIOXIDANT ACTIVITY; APOPTOSIS; ARTICLE; CELL CULTURE; CELL PROTECTION; CHICK; CYTOTOXICITY; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; EMBRYO; ENZYME INHIBITION; HEART MUSCLE CELL; IC 50; NERVE CELL; NONHUMAN; OXIDATIVE STRESS; RAT;

ALZHEIMER DISEASE; ANIMALS; ANTIOXIDANTS; APOPTOSIS; CARBAMATES; CHICKENS; CHOLINESTERASE INHIBITORS; HUMANS; INDOLES; NEURONS;

EID: 84870990188     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm301411g     Document Type: Article

References (59)

1. Coyle, J. T.; Price, D. L.; DeLong, M. R. Alzheimer's disease: a disorder of cortical cholinergic innervation Science 1983, 219, 1184-1190
2. Farlow, M.; Anand, R.; Messina, J., Jr.; Hartman, R.; Veach, J. A 52-week study of the efficacy of rivastigmine in patients with mild to moderately severe Alzheimer's disease Eur. Neurol. 2000, 44, 236-241
3. Farlow, M.; Gracon, S. I.; Hershey, L. A.; Lewis, K. W.; Sadowsky, C. H.; Dolan-Ureno, J. A controlled trial of tacrine in Alzheimer's disease. The Tacrine Study Group JAMA, J. Am. Med. Assoc. 1992, 268, 2523-2529
4. Feldman, H.; Gauthier, S.; Hecker, J.; Vellas, B.; Subbiah, P.; Whalen, E. A 24-week, randomized, double-blind study of donepezil in moderate to severe Alzheimer's disease Neurology 2001, 57, 613-620
5. Groner, E.; Ashani, Y.; Schorer-Apelbaum, D.; Sterling, J.; Herzig, Y.; Weinstock, M. The kinetics of inhibition of human acetylcholinesterase and butyrylcholinesterase by two series of novel carbamates Mol. Pharmacol. 2007, 71, 1610-1617
6. Weinstock, M. Selectivity of cholinesterase inhibition: clinical implications for the treatment of Alzheimer's disease CNS Drugs 1999, 12, 307-323
7. Darvesh, S.; Hopkins, D. A.; Geula, C. Neurobiology of butyrylcholinesterase Nature Rev. Neurosci. 2003, 4, 131-138
8. Mesulam, M.; Guillozet, A.; Shaw, P.; Quinn, B. Widely spread butyrylcholinesterase can hydrolyze acetylcholine in the normal and Alzheimer brain Neurobiol. Dis. 2002, 9, 88-93
9. Giacobini, E. Selective inhibitors of butyrylcholinesterase: a valid alternative for therapy of Alzheimer's disease? Drugs Aging 2001, 18, 891-898
10. Greig, N. H.; Utsuki, T.; Ingram, D. K.; Wang, Y.; Pepeu, G.; Scali, C.; Yu, Q. S.; Mamczarz, J.; Holloway, H. W.; Giordano, T.; Chen, D.; Furukawa, K.; Sambamurti, K.; Brossi, A.; Lahiri, D. K. Selective butyrylcholinesterase inhibition elevates brain acetylcholine, augments learning and lowers Alzheimer beta-amyloid peptide in rodent Proc. Natl. Acad. Sci. U. S. A. 2005, 102, 17213-17218
11. Ferris, S.; Nordberg, A.; Soininen, H.; Darreh-Shori, T.; Lane, R. Progression from mild cognitive impairment to Alzheimer's disease: effects of sex, butyrylcholinesterase genotype, and rivastigmine treatment Pharmacogenet. Genom. 2009, 19, 635-646
12. Bullock, R.; Dengiz, A. Cognitive performance in patients with Alzheimer's disease receiving cholinesterase inhibitors for up to 5 years Int. J. Clin. Pract. 2005, 59, 817-822
13. Smith, M. A.; Nunomura, A.; Lee, H. G.; Zhu, X.; Moreira, P. I.; Avila, J.; Perry, G. Chronological primacy of oxidative stress in Alzheimer disease Neurobiol. Aging 2005, 26, 579-580
14. Perry, G.; Castellani, R. J.; Moreira, P. I.; Lee, H. G.; Zhu, X.; Smith, M. A. Pathology's new role: defining disease process and protective responses Int. J. Clin. Exper. Pathol. 2008, 1, 1-4
15. Su, B.; Wang, X.; Lee, H. G.; Tabaton, M.; Perry, G.; Smith, M. A.; Zhu, X. Chronic oxidative stress causes increased tau phosphorylation in M17 neuroblastoma cells Neurosci. Lett. 2010, 468, 267-271
16. Arriagada, P. V.; Growdon, J. H.; Hedley-Whyte, E. T.; Hyman, B. T. Neurofibrillary tangles but not senile plaques parallel duration and severity of Alzheimer's disease Neurology 1992, 42 (3 Pt 1) 631-639
17. Butterfield, D. A.; Reed, T. T.; Perluigi, M.; De Marco, C.; Coccia, R.; Keller, J. N.; Markesbery, W. R.; Sultana, R. Elevated levels of 3-nitrotyrosine in brain from subjects with amnestic mild cognitive impairment: implications for the role of nitration in the progression of Alzheimer's disease Brain Res. 2007, 1148, 243-248
18. Nunomura, A.; Moreira, P. I.; Takeda, A.; Smith, M. A.; Perry, G. Oxidative RNA damage and neurodegeneration Curr. Med. Chem. 2007, 14, 2968-2975
19. Chyan, Y. J.; Poeggeler, B.; Omar, R. A.; Chain, D. G.; Frangione, B.; Ghiso, J.; Pappolla, M. A. Potent neuroprotective properties against the Alzheimer beta-amyloid by an endogenous melatonin-related indole structure, indole-3-propionic acid J. Biol. Chem. 1999, 274, 21937-21942
20. Zaikin, A., The cardioprotective effect of some novel compounds with antioxidant and/or radical scavenging activity. M.Sc. Thesis, The Hebrew University, Jerusalem, Israel, 2007.
21. Koncz, C. Characterisation of in Vitro Metabolites of TV-3326 in Hepatic Microsomal Preparations: Teva Final Report No. SB-2005-006; Biogal: Biogal: Budapest, 2007
22. Lerman, L. Potential neuroprotective derivatives of aminoindans and indoles. Inhibition of the reverse transcriptase (RT) enzyme of HIV virus as a potential treatment of AIDS. Ph.D. Thesis, Bar-Ilan University, Ramat-Gan, Israel, 2004.
23. Sterling, J.; Herzig, Y.; Goren, T.; Finkelstein, N.; Lerner, D.; Goldenberg, W.; Miskolczi, I.; Molnar, S.; Rantal, F.; Tamas, T.; Toth, G.; Zagyva, A.; Zekany, A.; Finberg, J.; Lavian, G.; Gross, A.; Friedman, R.; Razin, M.; Huang, W.; Krais, B.; Chorev, M.; Youdim, M. B.; Weinstock, M. Novel dual inhibitors of AChE and MAO derived from hydroxy aminoindan and phenethylamine as potential treatment for Alzheimer's disease J. Med. Chem. 2002, 45, 5260-5279
24. Harel, M.; Sussman, J. L.; Krejci, E.; Bon, S.; Chanal, P.; Massoulie, J.; Silman, I. Conversion of acetylcholinesterase to butyrylcholinesterase: modeling and mutagenesis Proc. Natl. Acad. Sci. U. S. A. 1992, 89, 10827-10831
25. Sterling, J.; Herzig, Y.; Goren, T.; Finkelstein, N.; Lerner, D.; Goldenberg, W.; Miskolczi, I.; Molnar, S.; Rantal, F.; Tamas, T. Novel dual inhibitors of AChE and MAO derived from hydroxy aminoindan and phenethylamine as potential treatment for Alzheimer's disease J. Med. Chem. 2002, 45, 5260-5279
26. Sussman, J. L.; Harel, M.; Frolow, F.; Oefner, C.; Goldman, A.; Toker, L.; Silman, I. Atomic structure of acetylcholinesterase from Torpedo californica: a prototypic acetylcholine-binding protein Science 1991, 253, 872-879
27. Inestrosa, N. C.; Alvarez, A.; Dinamarca, M. C.; Perez-Acle, T.; Colombres, M. Acetylcholinesterase-amyloid-beta-peptide interaction: effect of Congo Red and the role of the Wnt pathway Curr. Alzheimer Res. 2005, 2, 301-306
28. 2+ Inflammopharmacology 2004, 12, 289-303
29. Allegra, M.; Reiter, R. J.; Tan, D. X.; Gentile, C.; Tesoriere, L.; Livrea, M. A. The chemistry of melatonin's interaction with reactive species J. Pineal Res. 2003, 34, 1-10
30. Halliwell, B.; Whiteman, M. Measuring reactive species and oxidative damage in vivo and in cell culture: how should you do it and what do the results mean? Br. J. Pharmacol. 2004, 142, 231-255
31. Tan, D. X.; Reiter, R. J.; Manchester, L. C.; Yan, M. T.; El-Sawi, M.; Sainz, R. M.; Mayo, J. C.; Kohen, R.; Allegra, M.; Hardeland, R. Chemical and physical properties and potential mechanisms: melatonin as a broad spectrum antioxidant and free radical scavenger Curr. Top. Med. Chem. 2002, 2, 181-197
32. Harasimowicz, J.; Marques, K. L.; Silva, A. F.; Costa, R. C.; Prior, J. A.; Rodrigues, S. S.; Santos, J. L. Chemiluminometric evaluation of melatonin and selected melatonin precursors' interaction with reactive oxygen and nitrogen species Anal. Biochem. 2012, 420, 1-6
33. Halliwell, B.; Whiteman, M. Measuring reactive species and oxidative damage in vivo and in cell culture: how should you do it and what do the results mean? Br. J. Pharmacol. 2004, 142, 231-255
34. Hescheler, J.; Meyer, R.; Plant, S.; Krautwurst, D.; Rosenthal, W.; Schultz, G. Morphological, biochemical, and electrophysiological characterization of a clonal cell (H9c2) line from rat heart Circ. Res. 1991, 69, 1476-1486
35. Feldkamp, T.; Kribben, A.; Weinberg, J. M. Assessment of mitochondrial membrane potential in proximal tubules after hypoxia-reoxygenation Am. J. Physiol. Renal Physiol. 2005, 288, F1092-F1102
36. Woollacott, A. J.; Simpson, P. B. High throughput fluorescence assays for the measurement of mitochondrial activity in intact human neuroblastoma cells J. Biomol. Screening 2001, 6, 413-420
37. Maruyama, W.; Weinstock, M.; Youdim, M. B.; Nagai, M.; Naoi, M. Anti-apoptotic action of anti-Alzheimer drug, TV3326 [(N -propargyl)-(3 R)-aminoindan-5-yl]-ethyl methyl carbamate, a novel cholinesterase-monoamine oxidase inhibitor Neurosci. Lett. 2003, 341, 233-236
38. Desagher, S.; Osen-Sand, A.; Nichols, A.; Eskes, R.; Montessuit, S.; Lauper, S.; Maundrell, K.; Antonsson, B.; Martinou, J. C. Bid-induced conformational change of Bax is responsible for mitochondrial cytochrome c release during apoptosis J. Cell Biol. 1999, 144, 891-901
39. Narita, M.; Shimizu, S.; Ito, T.; Chittenden, T.; Lutz, R. J.; Matsuda, H.; Tsujimoto, Y. Bax interacts with the permeability transition pore to induce permeability transition and cytochrome c release in isolated mitochondria Proc. Natl. Acad. Sci. U. S. A. 1998, 95, 14681-14686
40. Lieven, C. J.; Thurber, K. A.; Levin, E. J.; Levin, L. A. Ordering of neuronal apoptosis signaling: a superoxide burst precedes mitochondrial cytochrome c release in a growth factor deprivation model Apoptosis: Int. J. Programmed Cell Death 2012, 17, 591-599
41. Lee, S. B.; Kim, J. J.; Kim, T. W.; Kim, B. S.; Lee, M. S.; Yoo, Y. D. Serum deprivation-induced reactive oxygen species production is mediated by Romo1 Apoptosis: Int. J. Programmed Cell Death 2010, 15, 204-218
42. Green, J. W., S.; Woodward, S. Selective Monoacylation of 2,2′-Binaphthol as a Route to New Monothiobinaphthol-Based Copper-Catalysts for Conjugate Addition Synlett 1995, 155-156
43. Smith, G. Indoles. Part I. The formylation of indole and some reactions of 3-formylindole J. Chem. Soc. 1954, 3842-3846
44. Silva, N. M.; Tributino, J. L. M.; Miranda, A. L. P.; Barreiro, E. J.; Fraga, C. A. M. New isoxazole derivatives designed as nicotinic acetylcholine receptor ligand candidates Eur. J. Med. Chem. 2002, 37, 163-170
45. Papageorgiou, G. C.; Corrie, J. E. T. Effects of aromatic substituents on the photocleavage of 1-acyl-7-nitroindolines Tetrahedron 2000, 56, 8197-8205
46. Gribble, G. W.; Lord, P. D.; Skotnick., J.; Dietz, S. E.; Eaton, J. T.; Johnson, J. L. Reactions of Sodium-Borohydride in Acidic Media 0.1. Reduction of Indoles and Alkylation of Aromatic-Amines with Carboxylic-Acids J. Am. Chem. Soc. 1974, 96, 7812-7814
47. Montagne, C.; Fournet, G.; Joseph, B. Synthesis of homocarbonyltopsentine derivatives Synthesis 2005, 136-146
48. Nudelman, A.; Patchornik, A., Indolylcephalosporin derivatives. U.S. Patent US4139703A 1979.
49. Xue, F. T.; Seto, C. T. Structure-activity studies of cyclic ketone inhibitors of the serine protease plasmin: design, synthesis, and biological activity Biorg. Med. Chem 2006, 14, 8467-8487
50. Georgiades, S. N.; Clardy, J. Total synthesis of psammaplysenes A and B, naturally occurring inhibitors of FOXO1a nuclear export Org. Lett. 2005, 7, 4091-4094
51. Dong, L.; Miller, M. J. Total synthesis of exochelin MN and analogues J. Org. Chem. 2002, 67, 4759-4770
52. Nishizawa, T.; Grüschow, S.; Jayamaha, D. H. E.; Nishizawa-Harada, C.; Sherman, D. H. Enzymatic assembly of the bis-indole core of rebeccamycin J. Am. Chem. Soc. 2006, 128, 724-725
53. Wells, G. J.; Tao, M.; Josef, K. A.; Bihovsky, R. 1,2-Benzothiazine 1,1-dioxide P-2-P-3 peptide mimetic aldehyde calpain I inhibitors J. Med. Chem. 2001, 44, 3488-3503
54. Kojima, T.; Niigata, K.; Fujikura, T.; Tachikawa, S.; Nozaki, Y.; Kagami, S.; Takahashi, K. Syntheses of (±)-2-[(inden-7-yloxy)methyl]morpholine hydrochloride (YM-08054, indeloxazine hydrochloride) and its derivatives with potential cerebral-activating and antidepressive properties Chem. Pharm. Bull. (Tokyo) 1985, 33, 3766-3774
55. Sinhababu, A. K.; Borchardt, R. T. Silica Gel-Assisted Reduction of Nitrostyrenes to 2-Aryl-1-Nitroalkanes with Sodium Borohydride Tetrahedron Lett. 1983, 24, 227-230
56. Ellman, G. L.; Courtney, K. D.; Andres, V., Jr.; Feather-Stone, R. M. A new and rapid colorimetric determination of acetylcholinesterase activity Biochem. Pharmacol. 1961, 7, 88-95
57. 2+ Inflammopharmacology 2004, 12, 289-303
58. Buxser, S. E.; Sawada, G.; Raub, T. J. Analytical and numerical techniques for evaluation of free radical damage in cultured cells using imaging cytometry and fluorescent indicators Methods Enzymol. 1999, 300, 256-275
59. Koren, E.; Kohen, R.; Ginsburg, I. A cobalt-based tetrazolium salts reduction test to assay polyphenols J. Agric. Food Chem. 2009, 57, 7644-7650