Design, Synthesis and Biological Evaluation of New 3,4-Dihydro-2(1H)-Quinolinone-Dithiocarbamate Derivatives as Multifunctional Agents for the Treatment of Alzheimer’s Disease

References

• Dunn B, Stein P, Temple R, Cavazzoni P. An appropriate use of accelerated approval - aducanumab for Alzheimer’s disease. N Engl J Med. 2021;385:856–857.
   PubMed Web of Science ®Google Scholar
• Zhang DF, Xu M, Bi R, et al. Genetic analyses of Alzheimer’s disease in China: achievements and perspectives. ACS Chem Neurosci. 2019;10:890–901. doi:10.1021/acschemneuro.8b00435
   PubMed Web of Science ®Google Scholar
• Rochoy M, Rivas V, Chazard E, et al. Factors associated with Alzheimer’s disease: an overview of reviews. J Prev Alzheimers Dis. 2019;6:121–134. doi:10.14283/jpad.2019.7
   PubMed Web of Science ®Google Scholar
• Ju Y, Tam KY. Pathological mechanisms and therapeutic strategies for Alzheimer’s disease. Neural Regen Res. 2022;17:543–549. doi:10.4103/1673-5374.320970
   PubMed Web of Science ®Google Scholar
• Mishra P, Kumar A, Panda G. Anti-cholinesterase hybrids as multi-target-directed ligands against Alzheimer’s disease (1998–2018). Bioorg Med Chem. 2019;27:895–930. doi:10.1016/j.bmc.2019.01.025
   PubMed Web of Science ®Google Scholar
• Villavicencio Tejo F, Quintanilla RA. Contribution of the Nrf2 pathway on oxidative damage and mitochondrial failure in Parkinson and Alzheimer’s disease. Antioxidants. 2021;10:1069–1100. doi:10.3390/antiox10071069
   Web of Science ®Google Scholar
• Bohnen NI, Grothe MJ, Ray NJ, et al. Recent advances in cholinergic imaging and cognitive decline-revisiting the cholinergic hypothesis of dementia. Curr Geriatr Rep. 2018;7:1–11. doi:10.1007/s13670-018-0234-4
   PubMed Web of Science ®Google Scholar
• Kabir MT, Uddin MS, Mamun AA, et al. Abdel-Daim, combination drug therapy for the management of Alzheimer’s disease. Int J Mol Sci. 2020;21:3272–3295. doi:10.3390/ijms21093272
   PubMed Web of Science ®Google Scholar
• Perry EK, Tomlinson BE, Blessed G, et al. Correlation of cholinergic abnormalities with senile plaques and mental test scores in senile dementia. Br Med J. 1978;2:1457–1459. doi:10.1136/bmj.2.6150.1457
   PubMed Web of Science ®Google Scholar
• Kucukoglu K, Gul H, Taslimi P, et al. Investigation of inhibitory properties of some hydrazone compounds on hCA I, hCA II and AChE enzymes. Bioorg Chem. 2019;86:316–321. doi:10.1016/j.bioorg.2019.02.008
   PubMed Web of Science ®Google Scholar
• Zhang Z, Guo J, Cheng M, et al. Design, synthesis, and biological evaluation of novel xanthone-alkylbenzylamine hybrids as multifunctional agents for the treatment of Alzheimer’s disease. Eur J Med Chem. 2021;213:113154. doi:10.1016/j.ejmech.2021.113154
   PubMed Web of Science ®Google Scholar
• Fu J, Bao F, Gu M, et al. Design, synthesis and evaluation of quinolinone derivatives containing dithiocarbamate moiety as multifunctional AChE inhibitors for the treatment of Alzheimer’s disease. J Enzyme Inhib Med Chem. 2020;35:118–128. doi:10.1080/14756366.2019.1687460
   PubMed Web of Science ®Google Scholar
• Han X, He G. Toward a rational design to regulate beta-Amyloid fibrillation for Alzheimer’s disease treatment. ACS Chem Neurosci. 2018;9:198–210. doi:10.1021/acschemneuro.7b00477
   PubMed Web of Science ®Google Scholar
• Shidore M, Machhi J, Shingala K, et al. Benzylpiperidine-linked diarylthiazoles as potential anti-Alzheimer’s agents: synthesis and biological evaluation. J Med Chem. 2016;59:5823–5846. doi:10.1021/acs.jmedchem.6b00426
   PubMed Web of Science ®Google Scholar
• Gao HW, Jiang YY, Zhan JY, et al. Pharmacophore-based drug design of AChE and BChE dual inhibitors as potential anti-Alzheimer’s disease agents. Bioorg Chem. 2021;114:105149. doi:10.1016/j.bioorg.2021.105149
   PubMed Web of Science ®Google Scholar
• Tripathi AC, Upadhyay S, Paliwal S, et al. Privileged scaffolds as MAO inhibitors: retrospect and prospects. Eur J Med Chem. 2018;145:445–497. doi:10.1016/j.ejmech.2018.01.003
   PubMed Web of Science ®Google Scholar
• Kumar B, Sheetal AK, Mantha AK, et al. Synthesis, biological evaluation and molecular modeling studies of phenyl-/benzhydrylpiperazine derivatives as potential MAO inhibitors. Bioorg Chem. 2018;77:252–262. doi:10.1016/j.bioorg.2018.01.020
   PubMed Web of Science ®Google Scholar
• Pathania A, Kumar R, Sandhir R. Hydroxytyrosol as anti-parkinsonian molecule: assessment using in-silico and MPTP-induced Parkinson’s disease model. Biomed Pharmacother. 2021;139:111525. doi:10.1016/j.biopha.2021.111525
   PubMed Web of Science ®Google Scholar
• Xie SS, Liu J, Tang C, et al. Design, synthesis and biological evaluation of rasagiline-clorgyline hybrids as novel dual inhibitors of monoamine oxidase-B and amyloid-beta aggregation against Alzheimer’s disease. Eur J Med Chem. 2020;202:112475. doi:10.1016/j.ejmech.2020.112475
   PubMed Web of Science ®Google Scholar
• Bolea I, Juarez-Jimenez J, de Los Rios C, et al. Samadi, Synthesis, biological evaluation, and molecular modeling of donepezil and N-[(5-(benzyloxy)-1-methyl-1H-indol-2-yl) methyl]-N-methylprop-2-yn-1-amine hybrids as new multipotent cholinesterase/monoamine oxidase inhibitors for the treatment of Alzheimer’s disease. J Med Chem. 2011;54:8251–8270. doi:10.1021/jm200853t
   PubMed Web of Science ®Google Scholar
• Jalal K, Khanb K, Haleema DJ, et al. In silico study to identify new monoamine oxidase type a (MAO-A) selective inhibitors from natural source by virtual screening and molecular dynamics simulation. J Mol Struct. 2022;1254:132244. doi:10.1016/j.molstruc.2021.132244
   Web of Science ®Google Scholar
• Rossi M, Freschi M, de Camargo Nascente L, et al. Sustainable drug discovery of multi-target-directed ligands for Alzheimer’s disease. J Med Chem. 2021;64:4972–4990. doi:10.1021/acs.jmedchem.1c00048
   PubMed Web of Science ®Google Scholar
• Cavalli A, Bolognesi ML, Minarini A, et al. Multi-target-directed ligands to combat neurodegenerative diseases. J Med Chem. 2008;51:347–372. doi:10.1021/jm7009364
   PubMed Web of Science ®Google Scholar
• Wang J, Cai P, Yang XL, et al. Novel cinnamamide-dibenzylamine hybrids: potent neurogenic agents with antioxidant, cholinergic, and neuroprotective properties as innovative drugs for Alzheimer’s disease. Eur J Med Chem. 2017;139:68–83. doi:10.1016/j.ejmech.2017.07.077
   PubMed Web of Science ®Google Scholar
• Carradori S, Silvestri R. New frontiers in selective human MAO-B inhibitors. J Med Chem. 2015;58:6717–6732. doi:10.1021/jm501690r
   PubMed Web of Science ®Google Scholar
• Jiang N, Ding J, Liu J, et al. Novel chromanone-dithiocarbamate hybrids as multifunctional AChE inhibitors with beta-amyloid anti-aggregation properties for the treatment of Alzheimer’s disease. Bioorg Chem. 2019;89:103027. doi:10.1016/j.bioorg.2019.103027
   PubMed Web of Science ®Google Scholar
• Sang Z, Pan W, Wang K, et al. Design, syntHesis and biological evaluation of 3,4-diHydro-2(1 H)-quinoline- O -alkylamine derivatives as new multipotent cHolinesterase/monoamine oxidase inHibitors for tHe treatment of AlzHeimer’s disease. Bioorg Med Chem. 2017;25:3006–3017. doi:10.1016/j.bmc.2017.03.070
   PubMed Web of Science ®Google Scholar
• Jiang N, Huang Q, Liu J, et al. Design, synthesis and biological evaluation of new coumarin-dithiocarbamate hybrids as multifunctional agents for the treatment of Alzheimer’s disease. Eur J Med Chem. 2018;146:287–298. doi:10.1016/j.ejmech.2018.01.055
   PubMed Web of Science ®Google Scholar
• Ellman G, Courtney K, Andres V, et al. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol. 1961;7:88–95.
   PubMed Web of Science ®Google Scholar
• Holt A, Sharman DF, Baker GB, et al. A continuous spectrophotometric assay for monoamine oxidase and related enzymes in tissue homogenates. Anal Biochem. 1997;244:384–392. doi:10.1006/abio.1996.9911
   PubMed Web of Science ®Google Scholar
• Yip LY, Aw CC, Lee SH, et al. The liver-gut microbiota axis modulates hepatotoxicity of tacrine in the rat. Hepatology. 2018;67:282–295. doi:10.1002/hep.29327
   PubMed Web of Science ®Google Scholar
• Knez D, Colettis N, Iacovino LG, et al. Stereoselective activity of 1-propargyl-4-styrylpiperidine-like analogues that can discriminate between monoamine oxidase isoforms A and B. J Med Chem. 2020;63:1361–1387. doi:10.1021/acs.jmedchem.9b01886
   PubMed Web of Science ®Google Scholar
• Greig NH, Utsuki T, Yu Q, et al. A new therapeutic target in Alzheimer’s disease treatment: attention to butyrylcholinesterase. Curr Med Res Opin. 2001;17:159–165. doi:10.1185/03007990152673800
   PubMed Web of Science ®Google Scholar
• He Q, Liu J, Lan JS, et al. Coumarin-dithiocarbamate hybrids as novel multitarget AChE and MAO-B inhibitors against Alzheimer’s disease: design, synthesis and biological evaluation. Bioorg Chem. 2018;81:512–528. doi:10.1016/j.bioorg.2018.09.010
   PubMed Web of Science ®Google Scholar
• Prashanth MK, Revanasiddappa HD, Lokanatha Rai KM, et al. Synthesis, characterization, antidepressant and antioxidant activity of novel piperamides bearing piperidine and piperazine analogues. Bioorg Med Chem Lett. 2012;22:7065–7070. doi:10.1016/j.bmcl.2012.09.089
   PubMed Web of Science ®Google Scholar
• Fu J, Cheng K, Zhang ZM, et al. Synthesis, structure and structure-activity relationship analysis of caffeic acid amides as potential antimicrobials. Eur J Med Chem. 2010;45:2638–2643. doi:10.1016/j.ejmech.2010.01.066
   PubMed Web of Science ®Google Scholar
• Wang Z, Wang Y, Li W, et al. Design, synthesis, and evaluation of multitarget-directed selenium-containing clioquinol derivatives for the treatment of Alzheimer’s disease. ACS Chem Neurosci. 2014;5:952–962. doi:10.1021/cn500119g
   PubMed Web of Science ®Google Scholar
• Bicker J, Alves G, Fortuna A, et al. A new PAMPA model using an in-house brain lipid extract for screening the blood-brain barrier permeability of drug candidates. Int J Pharm. 2016;501:102–111. doi:10.1016/j.ijpharm.2016.01.074
   PubMedGoogle Scholar
• Clemons K, Kretsch A, Verbeck G. Parallel artificial membrane permeability assay for blood-brain permeability determination of illicit drugs and synthetic analogues. Sci Justice. 2014;54:351–355. doi:10.1016/j.scijus.2014.06.004
   PubMed Web of Science ®Google Scholar
• Di L, Kerns EH, Fan K, et al. High throughput artificial membrane permeability assay for blood-brain barrier. Eur J Med Chem. 2003;38:223–232. doi:10.1016/S0223-5234(03)00012-6
   PubMed Web of Science ®Google Scholar
• Zhang Y, Huang N, Lu H, et al. Icariin protects against sodium azide-induced neurotoxicity by activating the PI3K/Akt/GSK-3beta signaling pathway. Peer J. 2020;8:e8955. doi:10.7717/peerj.8955
   PubMed Web of Science ®Google Scholar
• Wang K, Shi J, Zhou Y, et al. Design, synthesis and evaluation of cinnamic acid hybrids as multi-target-directed agents for the treatment of Alzheimer’s disease. Bioorg Chem. 2021;112:104879. doi:10.1016/j.bioorg.2021.104879
   PubMed Web of Science ®Google Scholar
• Zhong T, Feng M, Su M, et al. Qihuzha granule attenuated LPS-induced acute spleen injury in mice via Src/MAPK/Stat3 signal pathway. J Ethnopharmacol. 2021;281:114458. doi:10.1016/j.jep.2021.114458
   PubMed Web of Science ®Google Scholar