Design, synthesis, and biological evaluation of (E)-3,4-dihydroxystyryl aralkyl sulfones and sulfoxides as novel multifunctional neuroprotective agents

Journal of Medicinal Chemistry

Volumn 57, Issue 10, 2014, Pages 4302-4312

  Ning, Xianling ^a   Guo, Ying ^a   Wang, Xiaowei ^a   Ma, Xiaoyan ^a   Tian, Chao ^a   Shi, Xueqi ^a   Zhu, Renzong ^a   Cheng, Can ^b   Du, Yansheng ^c   Ma, Zhizhong ^a   Zhang, Zhili ^a   Liu, Junyi ^a  

^a PEKING UNIVERSITY HEALTH SCIENCE CENTER   (China)

^b JIANGXI UNIVERSITY OF TRADITIONAL CHINESE MEDICINE   (China)

^c INDIANA UNIVERSITY SCHOOL OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

(BENZYLSULFANYL)ACETIC ACID; (BENZYLSULFINYL)ACETIC ACID; (BENZYLSULFONYL)ACETIC ACID; (PHENETHYLSULFANYL)ACETIC ACID; (PHENETHYLSULFONYL)ACETIC ACID'; 3,4 DIHYDROXYSTYRYL ARALKYL SULFONE; 3,4 DIHYDROXYSTYRYL ARALKYL SULFOXIDE; 4 [2 (((4 (TRIFLUOROMETHYL)PHENYL)METHYL)SULFONYL)VINYL]BENZENE 1,2 DIOL; 4 [2 (((4 CHLOROPHENYL)METHYL)SULFONYL)VINYL]BENZENE 1,2 DIOL; 4 [2 (((4 METHOXYPHENYL)METHYL)SULFONYL)VINYL]BENZENE 1,2 DIOL; 4 [2 (((4 TERT BUTYLPHENYL)METHYL)SULFONYL)VINYL]BENZENE 1,2 DIOL; 4 [2 ((2 PHENYLETHYL)SULFONYL)VINYL]BENZENE 1,2 DIOL; 4 [2 ((3 PHENYLPROP 1 YL)SULFONYL)VINYL]BENZENE 1,2 DIOL; 4 [2 ((4 PHENYLBUT 1 YL)SULFONYL)VINYL]BENZENE 1,2 DIOL; 4 [2 ((PHENYLMETHYL)SULFONYL)VINYL]BENZENE 1,2 DIOL; ANTIOXIDANT; NEUROPROTECTIVE AGENT; SULFONE DERIVATIVE; SULFOXIDE; UNCLASSIFIED DRUG; UNINDEXED DRUG; [(3 PHENYLPROPYL)SULFANYL]ACETIC ACID; [(4 (TRIFLUOROMETHYL)BENZYL)SULFANYL]ACETIC ACID; [(4 (TRIFLUOROMETHYL)BENZYL)SULFONYL]ACETIC ACID; [(4 CHLOROBENZYL)SULFONYL]ACETIC ACID; [(4 METHOXYBENZYL)SULFANYL]ACETIC ACID; [(4 METHOXYBENZYL)SULFONYL]ACETIC ACID; [(4 PHENYLBUTYL)SULFANYL]ACETIC ACID; [(4 PHENYLBUTYL)SULFONYL]ACETIC ACID; [(4 TERT BUTYLBENZYL)SULFANYL]ACETIC ACID; [(4 TERT BUTYLBENZYL)SULFONYL]ACETIC ACID;

ANTIOXIDANT ACTIVITY; AQUEOUS SOLUTION; ARTICLE; BLOOD BRAIN BARRIER; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CELL DAMAGE; CELL VIABILITY; CONTROLLED STUDY; DNA DAMAGE; DRUG DESIGN; DRUG SCREENING; DRUG SYNTHESIS; KNOEVENAGEL CONDENSATION; MASS SPECTROMETRY; MEMBRANE PERMEABILITY; MEMBRANE TRANSPORT; MICROGLIA; MTT ASSAY; NEUROPROTECTION; OXIDATIVE PHOSPHORYLATION; PC12 CELL LINE; PROTON NUCLEAR MAGNETIC RESONANCE;

ANIMALS; BLOOD-BRAIN BARRIER; DRUG DESIGN; FREE RADICAL SCAVENGERS; HUMANS; NEUROPROTECTIVE AGENTS; NITRIC OXIDE; OXIDOPAMINE; PC12 CELLS; RATS; SULFONES; SULFOXIDES;

EID: 84901256728     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm500258v     Document Type: Article

References (47)

1. Goedert, M.; Spillantini, M. G. A century of Alzheimer's disease Science 2006, 314, 777-781
2. Mattson, M. P.; Magnus, T. Ageing and neuronal vulnerability Nat. Rev. Neurosci. 2006, 7, 278-294
3. Cini, M.; Moretti, A. Studies on lipid peroxidation and protein oxidation in the aging brain Neurobiol. Aging 1995, 16, 53-57
4. Heneka, M. T.; O'Banion, M. K. Inflammatory processes in Alzheimer's disease J. Neuroimmunol. 2007, 184, 69-91
5. Van der Schyf, C. J.; Geldenhuys, W. J.; Youdim, M. B. Multifunctional drugs with different CNS targets for neuropsychiatric disorders J. Neurochem. 2006, 99, 1033-1048
6. Chen, Y. J.; Shiao, M. S.; Wang, S. Y. The antioxidant caffeic acid phenethyl ester induces apoptosis associated with selective scavenging of hydrogen peroxide in human leukemic HL-60 cells Anticancer Drugs 2001, 12, 143-149
7. Orban, Z.; Mitsiades, N.; Burke, T. R., Jr.; Tsokos, M.; Chrousos, G. P. Caffeic acid phenethyl ester induces leukocyte apoptosis, modulates nuclear factor-kappa B and suppresses acute inflammation Neuroimmunomodulation 2000, 7, 99-105
8. Fesen, M. R.; Kohn, K. W.; Leteurtre, F.; Pommier, Y. Inhibitors of human immunodeficiency virus integrase Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 2399-2403
9. Kujumgiev, A.; Bankova, V.; Ignatova, A.; Popov, S. Antibacterial activity of propolis, some of its components and their analogs Pharmazie 1993, 48, 785-786
10. Natarajan, K.; Singh, S.; Burke, T. R., Jr.; Grunberger, D.; Aggarwal, B. B. Caffeic acid phenethyl ester is a potent and specific inhibitor of activation of nuclear transcription factor NF-kappa B Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 9090-9095
11. Lefkovits, I.; Su, Z.; Fisher, P.; Grunberger, D. Caffeic acid phenethyl ester profoundly modifies protein synthesis profile in type 5 adenovirus-transformed cloned rat embryo fibroblast cells Int. J. Oncol. 1997, 11, 59-67
12. Grunberger, D.; Banerjee, R.; Eisinger, K.; Oltz, E. M.; Efros, L.; Caldwell, M.; Estevez, V.; Nakanishi, K. Preferential cytotoxicity on tumor cells by caffeic acid phenethyl ester isolated from propolis Experientia 1988, 44, 230-232
13. Sud'ina, G. F.; Mirzoeva, O. K.; Pushkareva, M. A.; Korshunova, G. A.; Sumbatyan, N. V.; Varfolomeev, S. D. Caffeic acid phenethyl ester as a lipoxygenase inhibitor with antioxidant properties FEBS Lett. 1993, 329, 21-24
14. Toyoda, T.; Tsukamoto, T.; Takasu, S.; Shi, L.; Hirano, N.; Ban, H.; Kumagai, T.; Tatematsu, M. Anti-inflammatory effects of caffeic acid phenethyl ester (CAPE), a nuclear factor-κB inhibitor, on Helicobacter pylori -induced gastritis in Mongolian gerbils Int. J. Cancer 2009, 125, 1786-1795
15. Michaluart, P.; Masferrer, J. L.; Carothers, A. M.; Subbaramaiah, K.; Zweifel, B. S.; Koboldt, C.; Mestre, J. R.; Grunberger, D.; Sacks, P. G.; Tanabe, T.; Dannenberg, A. J. Inhibitory effects of caffeic acid phenethyl ester on the activity and expression of cyclooxygenase-2 in human oral epithelial cells and in a rat model of inflammation Cancer Res. 1999, 59, 2347-2352
16. Ma, Z.; Wei, X.; Fontanilla, C.; Noelker, C.; Dodel, R.; Hampel, H.; Du, Y. Caffeic acid phenethyl ester blocks free radical generation and 6-hydroxydopamine-induced neurotoxicity Life Sci. 2006, 79, 1307-1311
17. Wei, X.; Ma, Z.; Fontanilla, C. V.; Zhao, L.; Xu, Z. C.; Taggliabraci, V.; Johnstone, B. H.; Dodel, R. C.; Farlow, M. R.; Du, Y. Caffeic acid phenethyl ester prevents cerebellar granule neurons (CGNs) against glutamate-induced neurotoxicity Neuroscience 2008, 155, 1098-1105
18. Wei, X.; Zhao, L.; Ma, Z.; Holtzman, D. M.; Yan, C.; Dodel, R. C.; Hampel, H.; Oertel, W.; Farlow, M. R.; Du, Y. Caffeic acid phenethyl ester prevents neonatal hypoxic-ischaemic brain injury Brain 2004, 127, 2629-2635
19. Altug, M. E.; Serarslan, Y.; Bal, R.; Kontas, T.; Ekici, F.; Melek, I. M.; Aslan, H.; Duman, T. Caffeic acid phenethyl ester protects rabbit brains against permanent focal ischemia by antioxidant action: a biochemical and planimetric study Brain Res. 2008, 1201, 135-142
20. Fontanilla, C. V.; Ma, Z.; Wei, X.; Klotsche, J.; Zhao, L.; Wisniowski, P.; Dodel, R. C.; Farlow, M. R.; Oertel, W. H.; Du, Y. Caffeic acid phenethyl ester prevents 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine-induced neurodegeneration Neuroscience 2011, 188, 135-141
21. Noelker, C.; Bacher, M.; Gocke, P.; Wei, X.; Klockgether, T.; Du, Y.; Dodel, R. The flavanoide caffeic acid phenethyl ester blocks 6-hydroxydopamine-induced neurotoxicity Neurosci. Lett. 2005, 383, 39-43
22. Celli, N.; Dragani, L. K.; Murzilli, S.; Pagliani, T.; Poggi, A. In vitro and in vivo stability of caffeic acid phenethyl ester, a bioactive compound of propolis J. Agric. Food Chem. 2007, 55, 3398-3407
23. Wang, X.; Pang, J.; Maffucci, J. A.; Pade, D. S.; Newman, R. A.; Kerwin, S. M.; Bowman, P. D.; Stavchansky, S. Pharmacokinetics of caffeic acid phenethyl ester and its catechol-ring fluorinated derivative following intravenous administration to rats Biopharm. Drug Dispos. 2009, 30, 221-228
24. Rice-Evans, C. A.; Miller, N. J.; Paganga, G. Structure-antioxidant activity relationships of flavonoids and phenolic acids Free Radical Biol. Med. 1996, 20, 933-956
25. Lien, E. J.; Ren, S.; Bui, H. H.; Wang, R. Quantitative structure-activity relationship analysis of phenolic antioxidants Free Radical Biol. Med. 1999, 26, 285-294
26. Ning, X.; Guo, Y.; Ma, X.; Zhu, R.; Tian, C.; Wang, X.; Ma, Z.; Zhang, Z.; Liu, J. Synthesis and neuroprotective effect of E -3,4-dihydroxy styryl aralkyl ketones derivatives against oxidative stress and inflammation Bioorg. Med. Chem. Lett. 2013, 23, 3700-3703
27. Reddy, M. V.; Mallireddigari, M. R.; Cosenza, S. C.; Pallela, V. R.; Iqbal, N. M.; Robell, K. A.; Kang, A. D.; Reddy, E. P. Design, synthesis, and biological evaluation of (E)-styrylbenzylsulfones as novel anticancer agents J. Med. Chem. 2008, 51, 86-100
28. Reddy, M. V.; Venkatapuram, P.; Mallireddigari, M. R.; Pallela, V. R.; Cosenza, S. C.; Robell, K. A.; Akula, B.; Hoffman, B. S.; Reddy, E. P. Discovery of a clinical stage multi-kinase inhibitor sodium (E)-2-{2-methoxy-5- [(2′,4′,6′-trimethoxystyrylsulfonyl)methyl]phenylamino} acetate (ON 01910.Na): synthesis, structure-activity relationship, and biological activity J. Med. Chem. 2011, 54, 6254-6276
29. Wen, Z. H.; Chao, C. H.; Wu, M. H.; Sheu, J. H. A neuroprotective sulfone of marine origin and the in vivo anti-inflammatory activity of an analogue Eur. J. Med. Chem. 2010, 45, 5998-6004
30. Witty, D.; Ahmed, M.; Chuang, T. T. Advances in the design of 5-HT6 receptor ligands with therapeutic potential Prog. Med. Chem. 2009, 48, 163-224
31. Nagamine, T.; Inomata, K.; Endo, Y.; Paquette, L. A. Amino acid mediated intramolecular asymmetric aldol reaction to construct a new chiral bicyclic enedione containing a seven-membered ring: remarkable inversion of enantioselectivity compared to the six-membered ring example J. Org. Chem. 2007, 72, 123-131
32. Balducci, E.; Attolino, E.; Taddei, M. A stereoselective and practical synthesis of (E)-α,β-unsaturated ketones from aldehydes Eur. J. Org. Chem. 2011, 2011, 311-318
33. Gong, G.; Qin, Y.; Huang, W.; Zhou, S.; Wu, X.; Yang, X.; Zhao, Y.; Li, D. Protective effects of diosgenin in the hyperlipidemic rat model and in human vascular endothelial cells against hydrogen peroxide-induced apoptosis Chem.-Biol. Interact. 2010, 184, 366-375
34. Tirmenstein, M. A.; Hu, C. X.; Scicchitano, M. S.; Narayanan, P. K.; McFarland, D. C.; Thomas, H. C.; Schwartz, L. W. Effects of 6-hydroxydopamine on mitochondrial function and glutathione status in SH-SY5Y human neuroblastoma cells Toxicol. Vitro 2005, 19, 471-479
35. 2 and TNF-α in BV2 microglial cells via suppression of the NF-κB and MAPK pathway Toxicol. Vitro 2013, 27, 782-787
36. Cotelle, N.; Bernier, J. L.; Catteau, J. P.; Pommery, J.; Wallet, J. C.; Gaydou, E. M. Antioxidant properties of hydroxy-flavones Free Radical Biol. Med. 1996, 20, 35-43
37. Porcal, W.; Hernandez, P.; Gonzalez, M.; Ferreira, A.; Olea-Azar, C.; Cerecetto, H.; Castro, A. Heteroarylnitrones as drugs for neurodegenerative diseases: synthesis, neuroprotective properties, and free radical scavenger properties J. Med. Chem. 2008, 51, 6150-6159
38. Trippier, P. C.; Jansen Labby, K.; Hawker, D. D.; Mataka, J. J.; Silverman, R. B. Target- and mechanism-based therapeutics for neurodegenerative diseases: strength in numbers J. Med. Chem. 2013, 56, 3121-3147
39. Sultana, R.; Newman, S.; Mohmmad-Abdul, H.; Keller, J. N.; Butterfield, D. A. Protective effect of the xanthate, D609, on Alzheimer's amyloid β-peptide (1-42)-induced oxidative stress in primary neuronal cells Free Radical Res. 2004, 38, 449-458
40. Halleck, M. M.; Richburg, J. H.; Kauffman, F. C. Reversible and irreversible oxidant injury to PC12 cells by hydrogen peroxide Free Radical Biol. Med. 1992, 12, 137-144
41. Singh, S.; Swarnkar, S.; Goswami, P.; Nath, C. Astrocytes and microglia: responses to neuropathological conditions Int. J. Neurosci. 2011, 121, 589-597
42. Pehar, M.; Vargas, M. R.; Cassina, P.; Barbeito, A. G.; Beckman, J. S.; Barbeito, L. Complexity of astrocyte-motor neuron interactions in amyotrophic lateral sclerosis Neurodegener. Dis. 2005, 2, 139-146
43. Redondo, M.; Zarruk, J. G.; Ceballos, P.; Perez, D. I.; Perez, C.; Perez-Castillo, A.; Moro, M. A.; Brea, J.; Val, C.; Cadavid, M. I.; Loza, M. I.; Campillo, N. E.; Martinez, A.; Gil, C. Neuroprotective efficacy of quinazoline type phosphodiesterase 7 inhibitors in cellular cultures and experimental stroke model Eur. J. Med. Chem. 2012, 47, 175-185
44. 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
45. Wohnsland, F.; Faller, B. High-throughput permeability pH profile and high-throughput alkane/water log P with artificial membranes J. Med. Chem. 2001, 44, 923-930
46. Chen, X.; Murawski, A.; Patel, K.; Crespi, C. L.; Balimane, P. V. A novel design of artificial membrane for improving the PAMPA model Pharm. Res. 2008, 25, 1511-1520
47. Sugano, K.; Hamada, H.; Machida, M.; Ushio, H.; Saitoh, K.; Terada, K. Optimized conditions of bio-mimetic artificial membrane permeation assay Int. J. Pharm. 2001, 228, 181-188