Alzheımer Hastalığına Karşı İlaç Keşfinde Nitrojen Bileşiklerinin Rolü

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Referanslar

DeTure MA, Dickson DW. The neuropathological diagnosis of Alzheimer's disease. Molecular Neurodegeneration; 2019;14(1):32. doi:10.1186/s13024-019-0333-5

Collaborators GBDD. Global, regional, and national burden of Alzheimer's disease and other dementias, 1990-2016: a systematic analysis for the Global Burden of Disease Study 2016. The Lancet Neurology; 2019;18(1):88-106. doi:10.1016/S1474-4422(18)30403-4

Mishra CB, Shalini S, Gusain S, et al. Development of novel N-(6-methanesulfonyl-benzothiazol-2-yl)-3-(4-substituted-piperazin-1-yl)-propionamides with cholinesterase inhibition, anti-beta-amyloid aggregation, neuroprotection and cognition enhancing properties for the therapy of Alzheimer's disease. RSC Advances; 2020;10(30):17602-17619. doi: 10.1039/D0RA00663G

Tatiparti K, Sau S, Rauf MA, Iyer AK. Smart treatment strategies for alleviating tauopathy and neuroinflammation to improve clinical outcome in Alzheimer's disease. Drug Discovery Today; 2020;25(12):2110-2129. doi: 10.1016/j.drudis.2020.09.025.

Castellani RJ, Rolston RK, Smith MA. Alzheimer disease. Disease-a-month:DM; 2010;56(9):484-546. doi: 10.1016/j.disamonth.2010.06.001

Chen XQ, Mobley WC. Exploring the Pathogenesis of Alzheimer Disease in Basal Forebrain Cholinergic Neurons: Converging Insights From Alternative Hypotheses. Frontiers in Neuroscience; 2019;13:446. doi: 10.3389/fnins.2019.00446

Devenish SRA. The current landscape in Alzheimer's disease research and drug discovery. Drug Discovery Today; 2020;25(6):943-945. doi: 10.1016/j.drudis.2020.04.002

Khoury R, Rajamanickam J, Grossberg GT. An update on the safety of current therapies for Alzheimer's disease: focus on rivastigmine. Therapeutic Advances in Drug Safety.; 2018;9(3):171-178. doi: 10.1177/2042098617750555

Soria Lopez JA, Gonzalez HM, Leger GC. Alzheimer's disease. Handbook of Clinical Neurology; 2019;167:231-255. doi: 10.1016/B978-0-12-804766-8.00013-3

Watkins PB, Zimmerman HJ, Knapp MJ, Gracon SI, Lewis KW. Hepatotoxic effects of tacrine administration in patients with Alzheimer's disease. Jama;1994;271(13):992-998. doi:10.1001/jama.1994.03510370044030

Sharma K. Cholinesterase inhibitors as Alzheimer's therapeutics (Review). Molecular Medicine Reports; 2019;20(2):1479-1487. doi: 10.3892/mmr.2019.10374

Chaudhary A, Maurya PK, Yadav BS, et al. Current Therapeutic Targets for Alzheimer's Disease. Journal of Biomedicine; 2018;3:74-84. doi:10.7150/jbm.26783

Kumar A, Nisha CM, Silakari C, et al. Current and novel therapeutic molecules and targets in Alzheimer's disease. Journal of the Formosan Medical Association; 2016;115(1):3-10. doi: 10.1016/j.jfma.2015.04.001

Kumari S, Carmona AV, Tiwari AK, Trippier PC. Amide bond bioisosteres: Strategies, synthesis, and successes. Journal of Medicinal Chemistry; 2020;63(21):12290-12358. doi:10.1021/acs.jmedchem.0c00530

Morsy A, Trippier PC. Current and Emerging pharmacological targets for the treatment of Alzheimer's disease. Journal of Alzheimer's disease; 2019;72(s1):S145-S176. doi: 10.3233/JAD-190744

Morsy A, Trippier PC. Amyloid-binding alcohol dehydrogenase (ABAD) inhibitors for the treatment of Alzheimer's disease. Journal of Medicinal Chemistry; 2019;62(9):4252-4264. doi: 10.1021/acs.jmedchem.8b01530

Espinoza-Fonseca LM. The benefits of the multi-target approach in drug design and discovery. Bioorganic and Medicinal Chemistry; 2006;14(4):896-897. doi: 10.1016/j.bmc.2005.09.011

Trippier PC, Labby KJ, Hawker DD, et al. Target-and mechanism-based therapeutics for neurodegenerative diseases: strength in numbers. Journal of Medicinal Chemistry; 2013;56(8):3121-3147. doi: 10.1021/jm3015926

Martorana A, Giacalone V, Bonsignore R, et al. Heterocyclic scaffolds for the treatment of Alzheimer's disease. Current Pharmaceutical Design; 2016;22(26):3971-3995. doi: 10.2174/1381612822666160518141650

Hiremathad A, Piemontese L. Heterocyclic compounds as key structures for the interaction with old and new targets in Alzheimer's disease therapy. Neural Regeneration Research. 2017;12(8):1256-1261. doi: 10.4103/1673-5374.213541

Huang LK, Chao SP, Hu CJ. Clinical trials of new drugs for Alzheimer disease. Journal of Biomedical Science; 2020;27(1):18. doi: 10.1186/s12929-019-0609-7

Stoiljkovic M, Horvath TL, Hajos M. Therapy for Alzheimer's disease: Missing targets and functional markers? Ageing Research Reviews; 2021;68:101318. doi: 10.1016/j.arr.2021.101318

Jangid DK, Dhadda S. Phenacyl Bromide: an organic intermediate for synthesis of five- and six-membered bioactive heterocycles: Intechopen; 2019:1-17. doi: 10.5772/intechopen.88243

Heravi MM, Zadsirjan V. Prescribed drugs containing nitrogen heterocycles: an overview. RSC Advances; 2020;10(72):44247-44311. doi:10.1039/D0RA09198G

Lang DK, Kaur R, Arora R, et al. Nitrogen-containing heterocycles as anticancer agents: an overview. Anti-Cancer Agents in Medicinal Chemistry; 2020;20(18):2150-2168. doi: 10.2174/1871520620666200705214917

Kerru N, Gummidi L, Maddila S, et al. A review on recent advances in nitrogen-containing molecules and their biological applications. Molecules; 2020;25(8). doi: 10.3390/molecules25081909

Khan E. Pyridine derivatives as biologically active precursors; organics and selected coordination complexes. Chemistryselect; 2021;6(13):3041-3064. doi:10.1002/slct.202100332

Mohamed EA, Ismail NSM, Hagras M, et al. Medicinal attributes of pyridine scaffold as anticancer targeting agents. Future Journal of Pharmaceutical Sciences; 2021;7(1). doi:10.1186/s43094-020-00165-4

Altaf AA, Shahzad A, Gul Z, et al. A Review on the medicinal importance of pyridine derivatives. Journal of Drug Design and Medicinal Chemistry; 2015;1(1):1-11. doi: 10.11648/j.jddmc.20150101.11

Sekioka R, Honda S, Akashiba H, et al. Optimization and biological evaluation of imidazopyridine derivatives as a novel scaffold for gamma-secretase modulators with oral efficacy against cognitive deficits in Alzheimer's disease model mice. Bioorganic and Medicinal Chemistry; 2020;28(11):115455. doi: 10.1016/j.bmc.2020.115455

Wolfe MS. Gamma-Secretase modulators. Current Alzheimer Research; 2007;4(5):571-573. doi: 10.2174/156720507783018299

Wolfe MS. Gamma-Secretase inhibitors and modulators for Alzheimer's disease. Journal of Neurochemistry; 2012;120 Suppl 1(Suppl 1):89-98. doi: 10.1111/j.1471-4159.2011.07501.x

de Los Rios C, Marco-Contelles J. Tacrines for Alzheimer's disease therapy. III. The pyrido tacrines. European Journal of Medicinal Chemistry; 2019;166:381-389. doi: 10.1016/j.ejmech.2019.02.005

Patocka J, Jun D, Kuca K. Possible role of hydroxylated metabolites of tacrine in drug toxicity and therapy of Alzheimer's disease. Current Drug Metabolism; 2008;9(4):332-335. doi: 10.2174/138920008784220619

Mufson EJ, Counts SE, Perez SE, et al. Cholinergic system during the progression of Alzheimer's disease: therapeutic implications. Expert Review of Neurotherapeutics; 2008;8(11):1703-1718. doi: 10.1586/14737175.8.11.1703

Ferreira-Vieira TH, Guimaraes IM, Silva FR, et al. Alzheimer's disease: Targeting the cholinergic system. Current Neuropharmacology; 2016;14(1):101-115. doi: 10.2174/1570159X13666150716165726

Chopra K, Misra S, Kuhad A. Current perspectives on pharmacotherapy of Alzheimer's disease. Expert Opinion on Pharmacotherapy; 2011;12(3):335-350. doi: 10.1517/14656566.2011.520702

Easmon J, Purstinger G, Heinisch G, et al. Synthesis, cytotoxicity, and antitumor activity of copper(II) and iron(II) complexes of (4)N-azabicyclo[3.2.2]nonane thiosemicarbazones derived from acyl diazines. Journal of Medicinal Chemistry; 2001;44(13):2164-2171. doi: 10.1021/jm000979z

Sharma V, Chitranshi N, Agarwal AK. Significance and biological importance of pyrimidine in the microbial world. International Journal of Medicinal Chemistry; 2014;2014:202784. doi: 10.1155/2014/202784

Wermuth CG. Are pyridazines privileged structures? Medicinal Chemistry Communication; 2011;2:935-941. doi: 10.1039/C1MD00074H

Nakagami Y, Nishimura S, Murasugi T, et al. A novel beta-sheet breaker, RS-0406, reverses amyloid beta-induced cytotoxicity and impairment of long-term potentiation in vitro. British Journal of Pharmacology; 2002;137(5):676-682. doi: 10.1038/sj.bjp.0704911

O'Hare E, Scopes DI, Treherne JM, et al. RS-0406 arrests amyloid-beta oligomer-induced behavioural deterioration in vivo. Behavioural Brain Research; 2010;210(1):32-37. doi: 10.1016/j.bbr.2010.01.044

Y. Fang, W. Xia, B. Cheng et al. Design, synthesis, and biological evaluation of compounds with a new scaffold as anti-neuroinflammatory agents for the treatment of Alzheimer's disease. European Journal of Medicinal Chemistry; 2018;149:129-138. doi: 10.1016/j.ejmech.2018.02.063

Zhou W, Zhong G, Fu S, et al. Microglia-based phenotypic screening identifies a novel inhibitor of neuroinflammation effective in Alzheimer's disease models. ACS Chemical Neuroscience; 2016;7(11):1499-1507. doi: 10.1021/acschemneuro.6b00125

Du H, Yan SS. Mitochondrial permeability transition pore in Alzheimer's disease: cyclophilin D and amyloid beta. Biochimica et Biophysica Acta; 2010;1802(1):198-204. doi: 10.1016/j.bbadis.2009.07.005

Perez MJ, Ponce DP, Aranguiz A, et al. Mitochondrial permeability transition pore contributes to mitochondrial dysfunction in fibroblasts of patients with sporadic Alzheimer's disease. Redox Biology; 2018;19:290-300. doi: 10.1016/j.redox.2018.09.001

Elkamhawy A, Park JE, Hassan AHE, et al. Pyrazinyl ureas revisited: 1-(3-(Benzyloxy)pyrazin-2-yl)-3-(3,4-dichlorophenyl)urea, a new blocker of Abeta-induced mPTP opening for Alzheimer's disease. European Journal of Medicinal Chemistry; 2018;157:268-278. doi: 10.1016/j.ejmech.2018.07.068

Elkamhawy A, Park JE, Hassan AHE, et al. Synthesis and evaluation of 2-(3-arylureido)pyridines and 2-(3-arylureido)pyrazines as potential modulators of Abeta-induced mitochondrial dysfunction in Alzheimer's disease. European Journal of Medicinal Chemistry; 2018;144:529-543. doi: 10.1016/j.ejmech.2017.12.045

Park JE, Elkamhawy A, Hassan AHE, et al. Synthesis and evaluation of new pyridyl/pyrazinyl thiourea derivatives: Neuroprotection against amyloid-beta-induced toxicity. European Journal of Medicinal Chemistry; 2017;141:322-334. doi:10.1016/j.ejmech.2017.09.043

Ye Z, Adhikari S, Xia Y, et al. Expedient syntheses of N-heterocycles via intermolecular amphoteric diamination of allenes. Nature Communications; 2018;9(1):721. doi: 10.1038/s41467-018-03085-3

Jalageri MD, Nagaraja A, Puttaiahgowda YM. Piperazine based antimicrobial polymers: a review. RSC Advances; 2021;11(25):15213-15230. doi:10.1039/D1RA00341K

Mishra CB, Manral A, Kumari S, et al. Design, synthesis and evaluation of novel indandione derivatives as multifunctional agents with cholinesterase inhibition, anti-beta-amyloid aggregation, antioxidant and neuroprotection properties against Alzheimer's disease. Bioorganic and Medicinal Chemistry; 2016;24(16):3829-3841. doi: 10.1016/j.bmc.2016.06.027

Shin CY, Kim HS, Cha KH, et al. The Effects of Donepezil, an acetylcholinesterase inhibitor, on impaired learning and memory in rodents. Biomolecules and Therapeutics; 2018;26(3):274-281. doi: 10.4062/biomolther.2017.189

Ono K, Hasegawa K, Naiki H, et al. Curcumin has potent anti-amyloidogenic effects for Alzheimer's beta-amyloid fibrils in vitro. Journal of Neuroscience Research; 2004;75(6):742-750. doi: 10.1002/jnr.20025

Shachar DB, Kahana N, Kampel V, et al. Neuroprotection by a novel brain permeable iron chelator, VK-28, against 6-hydroxydopamine lession in rats. Neuropharmacology. 2004;46(2):254-263. doi: 10.1016/j.neuropharm.2003.09.005

Lecanu L, Tillement L, McCourty A, et al. Dimethyl-carbamic acid 2,3-bis-dimethylcarbamoyloxy-6-(4-ethyl-piperazine-1-carbonyl)-phenyl ester: a novel multi-target therapeutic approach to neuroprotection. Medicinal Chemistry; 2010;6(3):123-140. doi: 10.2174/1573406411006030123

Mishra CB, Kumari S, Manral A, et al. Design, synthesis, in-silico and biological evaluation of novel donepezil derivatives as multi-target-directed ligands for the treatment of Alzheimer's disease. European Journal of Medicinal Chemistry; 2017;125:736-750. doi: 10.1016/j.ejmech.2016.09.057

Goel P, Alam O, Naim MJ, et al. Recent advancement of piperidine moiety in treatment of cancer- A review. European Journal of Medicinal Chemistry; 2018;157:480-502. doi: 10.1016/j.ejmech.2018.08.017

Moussa-Pacha NM, Abdin SM, Omar HA, et al. BACE1 inhibitors: Current status and future directions in treating Alzheimer's disease. Medicinal Research Reviews; 2020;40(1):339-384. doi: 10.1002/med.21622

Coimbra JR, Sobral PJ, Santos AE, et al. An overview of glutaminyl cyclase inhibitors for Alzheimer's disease. Future Medicinal Chemistry; 2019;11(24):3179-3194. doi: 10.4155/fmc-2019-0163

McKinzie DL, Winneroski LL, Green SJ, et al. Discovery and early clinical development of LY3202626, a low-dose, CNS-penetrant BACE inhibitor. Journal of Medicinal Chemistry; 2021;64(12):8076-8100. doi:10.1021/acs.jmedchem.1c00489

Costanzo P, Cariati L, Desiderio D, et al. Design, synthesis, and evaluation of Donepezil-like compounds as AChE and BACE-1 inhibitors. ACS Medicinal Chemistry Letters; 2016;7(5):470-475. doi:10.1021/acsmedchemlett.5b00483

Shaikh S, Dhavan P, Pavale G, et al. Design, synthesis and evaluation of pyrazole bearing alpha-aminophosphonate derivatives as potential acetylcholinesterase inhibitors against Alzheimer's disease. Bioorganic Chemistry; 2020;96:103589. doi: 10.1016/j.bioorg.2020.103589

Zhang Z, Min J, Chen M, et al. The structure-based optimization of delta-sultone-fused pyrazoles as selective BuChE inhibitors. European Journal of Medicinal Chemistry; 2020;201:112273. doi:10.1016/j.ejmech.2020.112273

Elguero J. Tautomerism: A Historical perspective. In: Antonov L, ed: Wiley-VCH Verlag GmbH & Co. KGaA. ; 2016:1-10.

N. Xi, Q. Huang, Liu L. Imidazoles In: A.R. Katritzky, C.A. Ramsden, E.F.V. Scriven, Taylo RJK, eds. Comprehensive Heterocyclic Chemistry III: Elsevier; 2008:143-364.

Zhang L, Peng XM, Damu GL, et al. Comprehensive review in current developments of imidazole-based medicinal chemistry. Medicinal Research Reviews; 2014;34(2):340-437. doi: 10.1002/med.21290

Alghamdi SS, Suliman RS, Almutairi K, et al. Imidazole as a promising medicinal scaffold: current status and future direction. Drug Design, Development and Therapy; 2021;15:3289-3312. doi: 10.2147/DDDT.S307113

Kametani F, Hasegawa M. Reconsideration of amyloid hypothesis and Tau hypothesis in Alzheimer's disease. Frontiers in Neuroscience; 2018;12:25. doi: 10.3389/fnins.2018.00025

Chen GF, Xu TH, Yan Y, et al. Amyloid beta: structure, biology and structure-based therapeutic development. Acta Pharmacologica Sinica; 2017;38(9):1205-1235. doi: 10.1038/aps.2017.28

Nussbaum JM, Schilling S, Cynis H, et al. Prion-like behaviour and tau-dependent cytotoxicity of pyroglutamylated amyloid-beta. Nature; 2012;485(7400):651-655. doi: 10.1038/nature11060

Li M, Dong Y, Yu X, et al. Synthesis and evaluation of diphenyl conjugated imidazole derivatives as potential glutaminyl cyclase inhibitors for treatment of Alzheimer's Disease. Journal of Medicinal Chemistry; 2017;60(15):6664-6677. doi:10.1021/acs.jmedchem.7b00648

Souza R, Miranda L. Strategies towards the synthesis of N2-substituted 1,2,3-triazoles. Anais da Academia Brasileira de Ciencias; 2019;91(suppl 1):e20180751. doi: 10.1590/0001-3765201820180751

Aggarwal R, Sumran G. An insight on medicinal attributes of 1,2,4-triazoles. European Journal of Medicinal Chemistry; 2020;205:112652. doi: 10.1016/j.ejmech.2020.112652

Kharb R, Sharma PC, Yar MS. Pharmacological significance of triazole scaffold. Journal of Enzyme Inhibition and Medicinal Chemistry; 2011;26(1):1-21. doi: 10.3109/14756360903524304

Bonandi E, Christodoulou MS, Fumagalli G, et al. The 1,2,3-triazole ring as a bioisostere in medicinal chemistry. Drug Discovery Today; 2017;22(10):1572-1581. doi: 10.1016/j.drudis.2017.05.014

Murakami K, Watanabe T, Koike T, et al. Pharmacological properties of a novel and potent gamma-secretase modulator as a therapeutic option for the treatment of Alzheimer's disease. Brain Research; 2016;1633:73-86. doi: 10.1016/j.brainres.2015.12.016

Yazdani M, Edraki N, Badri R, et al. Multi-target inhibitors against Alzheimer disease derived from 3-hydrazinyl 1,2,4-triazine scaffold containing pendant phenoxy methyl-1,2,3-triazole: Design, synthesis and biological evaluation. Bioorganic Chemistry; 2019;84:363-371. doi: 10.1016/j.bioorg.2018.11.038

Iraji A, Firuzi O, Khoshneviszadeh M, et al. Synthesis and structure-activity relationship study of multi-target triazine derivatives as innovative candidates for treatment of Alzheimer's disease. Bioorganic Chemistry; 2018;77:223-235. doi: 10.1016/j.bioorg.2018.01.017

Neochoritis CG, Zhao T, Domling A. Tetrazoles via multicomponent reactions. Chemical Reviews; 2019;119(3):1970-2042. doi: 10.1021/acs.chemrev.8b00564

Zou Y, Liu L, Liu J, et al. Bioisosteres in drug discovery: focus on tetrazole. Future Medicinal Chemistry; 2020;12(2):91-93. doi: 10.4155/fmc-2019-0288

Lassalas P, Gay B, Lasfargeas C, et al. Structure property relationships of carboxylic acid isosteres. Journal of Medicinal Chemistry; 2016;59(7):3183-3203. doi: 10.1021/acs.jmedchem.5b01963

Patani GA, LaVoie EJ. Bioisosterism: A rational approach in drug design. Chemical Reviews; 1996;96(8):3147-3176. doi: 10.1021/cr950066q

Malik MA, Wani MY, AL-Thabaiti SA, et al. Tetrazoles as carboxylic acid isosteres: chemistry and biology. Journal of Inclusion Phenomena Macrocyclic Chemistry; 2014;78:15–37. doi:10.1007/s10847-013-0334-x

Kushwaha P, Fatima S, Upadhyay A, et al. Synthesis, biological evaluation and molecular dynamic simulations of novel Benzofuran-tetrazole derivatives as potential agents against Alzheimer's disease. Bioorganic and Medicinal Chemistry Letters; 2019;29(1):66-72. doi: 10.1016/j.bmcl.2018.11.005

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