Abstract
Neurodegenerative diseases like alzheimer’s disease, Parkinson disease have affected a large number of people worldwide and these numbers are increasing rapidly. Treatments for these disorders are generally targeted on giving symptomatic relief and are not curable. Research for newer molecules is ongoing and pharmacological significance of heterocycles. Triazole and tetrazole are emerging as new moieties in this area. In this review, we have included various methodologies of synthesizing triazoles and tetrazoles and evaluation of these derivatives in modulating activity of different enzymes like cholinesterases, GSK-3β, monoamine oxidases, BACE-1, DYRK, COX-2 and tyrosinase. Tyrosinase catalyzes metabolic processes which cause neurodegeneration of neuronal cells in patients suffering from Parkinson’s disease. Other attributes playing role in imparting relief in neurodegenerative diseases such as anti-inflammatory and anti-oxidant properties were also described. These azoles derivatives also target receptors like NMDA and P2X7 which are responsible for regulating conditions of patients suffering from alzheimer’s disease and amyotrophic lateral sclerosis.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Abrahamsson K, Andersson P, Bergman J et al (2016) Discovery of AZD8165—a clinical candidate from a novel series of neutral thrombin inhibitors. Med Chem Comm 7:272–281. https://doi.org/10.1039/c5md00479a
Arabi AA (2017) Routes to drug design via bioisosterism of carboxyl and sulfonamide groups. Future Med Chem 9:2167–2180. https://doi.org/10.4155/fmc-2017-0136
Aziz O, Bürli RW, Fischer DF et al (2014) Towards small molecules as therapies for alzheimer’s disease and other neurodegenerative disorders. Elsevier
Beebe J, Zhang JT (2019) CC-115, a dual mammalian target of rapamycin/DNA-dependent protein kinase inhibitor in clinical trial, is a substrate of ATP-binding cassette G2, a risk factor for CC-115 resistance. J Pharmacol Exp Ther 371:320–326. https://doi.org/10.1124/jpet.119.258392
Benson FR (1947) The chemistry of the tetrazoles. Chem Rev 41:1–61. https://doi.org/10.1021/cr60128a001
Bernard-Gauthier V, Mossine AV, Knight A et al (2019) Structural basis for achieving GSK-3β inhibition with high potency, selectivity, and brain exposure for positron emission tomography imaging and drug discovery. J Med Chem 62:9600–9617. https://doi.org/10.1021/acs.jmedchem.9b01030
Bianca LS, Leite JPV, Mendes TAO, Varejao EVV, Chaves ACS, da silva JG, Agrizzi AP, Ferreira PG, Pilau EJ, dos Santos ESMH (2021) Inhibition of acetylcholinesterase by coumarin-linked amino acids sunthesized via triazole associated with molecule partition coefficient. J Brazil Chem Soc 32:652–664
Bousada GM, de Sousa BL, Furlani G, et al (2020) Tyrosol 1,2,3-triazole analogues as new acetylcholinesterase (AChE) inhibitors. Comput Biol Chem 88:107359. https://doi.org/10.1016/j.compbiolchem.2020.107359
Brahimi FT, Belkhadem F, Trari B, Othman AA (2020) Diazole and triazole derivatives of castor oil extract: synthesis, hypoglycemic effect, antioxidant potential and antimicrobial activity. Grasas Aceites 71:1–12. https://doi.org/10.3989/gya.0342191
Can NNC, Osmaniye D, Levent S, et al (2017) Synthesis of new hydrazone derivatives for MAO enzymes inhibitory activity. Molecules 22. https://doi.org/10.3390/molecules22081381
Carballo-Carbajal I, Laguna A, Romero-Giménez J, et al (2019) Brain tyrosinase overexpression implicates age-dependent neuromelanin production in Parkinson’s disease pathogenesis. Nat Commun 10. https://doi.org/10.1038/s41467-019-08858-y
Cardoso CS, Silva DPB, Silva DM et al (2020) Mechanisms involved in the antinociceptive and anti-inflammatory effects of a new triazole derivative: 5-[1-(4-fluorophenyl)-1H-1,2,3-triazol-4-yl]-1H-tetrazole (LQFM-096). Inflammopharmacol 28:877–892. https://doi.org/10.1007/s10787-020-00685-8
Cassano T, Calcagnini S, Carbone A et al (2019) Pharmacological treatment of depression in alzheimer’s disease: a challenging task. Front Pharmacol 10:1–10. https://doi.org/10.3389/fphar.2019.01067
Chen L, Zhang X, Peng X et al (2019) Baicalin tetrazole acts as anti-pneumocystis carinii pneumonia candidate in immunosuppressed rat model. Microb Pathog 132:59–65. https://doi.org/10.1016/j.micpath.2019.04.027
Choi J, Choi KE, Park SJ et al (2016) Ensemble-Based virtual screening led to the discovery of new classes of potent tyrosinase inhibitors. J Chem Inf Model 56:354–367. https://doi.org/10.1021/acs.jcim.5b00484
Cox JR, Woodcock S, Hillier IH (1990) Combined ab initio quantum mechanics and free energy perturbation study. J Phys Chem 94:5499–5501. https://doi.org/10.1021/j100377a016
Darwish SS, Abdel-Halim M, ElHady AK et al (2018) Development of novel amide–derivatized 2,4-bispyridyl thiophenes as highly potent and selective Dyrk1A inhibitors. Part II: Identification of the cyclopropylamide moiety as a key modification. Eur J Med Chem 158:270–285. https://doi.org/10.1016/j.ejmech.2018.08.097
De Freitas Silva M, Lima ET, Pruccoli L, et al (2020) Design, synthesis and biological evaluation of novel triazole N-acylhydrazone hybrids for alzheimer’s disease. Molecules 25:1–18. https://doi.org/10.3390/molecules25143165
de Oliveira LP, da Silva DPB, Florentino IF, et al (2017) New pyrazole derivative 5-[1-(4-fluorophenyl)-1H-pyrazol-4-yl]-2H-tetrazole: synthesis and assessment of some biological activities. Chem Biol Drug Des 89:124–135. https://doi.org/10.1111/cbdd.12838
Derrick JS, Lim MH (2015) Tools of the trade: investigations into design strategies of small molecules to target components in alzheimer’s disease. ChemBioChem 16:887–898. https://doi.org/10.1002/cbic.201402718
Di Pietro O, Alencar N, Esteban G, et al (2016) Design, synthesis and biological evaluation of N-methyl-N-[(1,2,3-triazol-4-yl)alkyl]propargylamines as novel monoamine oxidase B inhibitors. Bioorganic Med Chem 24:4835–4854. https://doi.org/10.1016/j.bmc.2016.06.045
Dişli A, Gümüs M, ünal K, et al (2018) New multifunctional agents and their inhibitory effects on the acetyl cholinesterase enzyme. Maced J Chem Chem Eng 37:21–34. https://doi.org/10.20450/mjcce.2017.1334
Eftekhar M, Eshghi H, Rahimizadeh M, et al (2014) Facile synthesis of some novel 6-alkyl or aryl-7H-tetrazolo[5,1-b][1,3,4] thiadiazine. J Chem Res 38:365–367. 10.3184%2F174751914X14001496962946
El-Mekabaty A (2015) Synthesis and antioxidant activity of some new heterocycles incorporating the pyrazolo-[3,4-D]pyrimidin-4-one moiety. Chem Heterocycl Compd 50:1698–1706. https://doi.org/10.1007/s10593-015-1640-6
Ganesh T, Banik A, Dingledine R et al (2018) Peripherally restricted, highly potent, selective, aqueous-soluble EP2 antagonist with anti-inflammatory properties. Mol Pharm 15:5809–5817. https://doi.org/10.1021/acs.molpharmaceut.8b00764
Ghosh AK, Osswald HL (2014) BACE1 (β-secretase) inhibitors for the treatment of alzheimer’s disease. Chem Soc Rev 43:6765–6813. https://doi.org/10.1039/c3cs60460h
Gouda MA, Al-Ghorbani M, Helal MH, et al (2020) A review: recent progress on the synthetic routes to 1(5)-substituted 1H-Tetrazoles and its analogs. Synth Commun 0:1–27. https://doi.org/10.1080/00397911.2020.1792499
Hamada YUK (2018) Design of anti-alzheimer’s disease agents focusing on a specific interaction with target biomolecules. In: Roy K (ed) Computational modeling of drugs against alzheimer’s disease. Humana Press, New York, NY, pp 207–228
Hameed A, Zehra ST, Abbas S et al (2016) One-pot synthesis of tetrazole-1,2,5,6-tetrahydronicotinonitriles and cholinesterase inhibition: probing the plausible reaction mechanism via computational studies. Bioorg Chem 65:38–47. https://doi.org/10.1016/j.bioorg.2016.01.004
Hashim SC, Alias MF (2012) Synthesis, spectroscopic study of Pt (IV), Au (III), Rh(III),Co(II) and V (IV) complexes with sodium[5-(p-nitro phenyl) -/4- phenyl-1,2,4-triazole-3-dithiocarbamato hydrazide] and cytotoxicity assay on rhabdomyosarcoma cell line of heavy metals. Baghdad Sci J 9:668–679. https://doi.org/10.21123/bsj.9.4.668-679
Heider F, Pantsar T, Kudolo M et al (2019) Pyridinylimidazoles as GSK3β inhibitors: the impact of tautomerism on compound activity via water networks. ACS Med Chem Lett 10:1407–1414. https://doi.org/10.1021/acsmedchemlett.9b00177
Himo F, Lovell T, Hilgraf R et al (2005) Copper(I)-catalyzed synthesis of azoles. DFT study predicts unprecedented reactivity and intermediates. J Am Chem Soc 127:210–216. https://doi.org/10.1021/ja0471525
Iraji A, Firuzi O, Khoshneviszadeh M et al (2017) Multifunctional iminochromene-2H-carboxamide derivatives containing different aminomethylene triazole with BACE1 inhibitory, neuroprotective and metal chelating properties targeting alzheimer’s disease. Eur J Med Chem 141:690–702. https://doi.org/10.1016/j.ejmech.2017.09.057
Jain A, Piplani P (2020) Design, synthesis and biological evaluation of triazole-oxadiazole conjugates for the management of cognitive dysfunction. Bioorg Chem 103:104151. https://doi.org/10.1016/j.bioorg.2020.104151
Jawabrah Al-Hourani B, Sharma SK, Kaur J, Wuest F (2015) Synthesis, bioassay studies, and molecular docking of novel 5-substituted 1H tetrazoles as cyclooxygenase-2 (COX-2) inhibitors. Med Chem Res 24:78–85. https://doi.org/10.1007/s00044-014-1102-1
Jawabrah Al-Hourani B, Al-Awaida W, Matalka KZ, et al (2016) Structure–activity relationship of novel series of 1,5-disubstituted tetrazoles as cyclooxygenase-2 inhibitors: design, synthesis, bioassay screening and molecular docking studies. Bioorganic Med Chem Lett 26:4757–4762. https://doi.org/10.1016/j.bmcl.2016.08.034
Jiaranaikulwanitch J, Tadtong S, Govitrapong P et al (2017) Neuritogenic activity of bi-functional bis-tryptoline triazole. Bioorganic Med Chem 25:1195–1201. https://doi.org/10.1016/j.bmc.2016.12.027
Jones TW, Spuhler-Phillips K, Wilson W, Leslie SW (1996) D, L-(Tetrazol-5-yl)glycine stimulation of NMDA receptors in neonatal dissociated neurons: inhibition by ethanol. Alcohol 13:181–185. https://doi.org/10.1016/0741-8329(95)02041-1
Kadambar AK, Kalluraya B, Singh S et al (2021) One-pot three-component azide-alkyne cycloaddition: Synthesis of new pyrazole, 1,2,3-triazole, and oxadiazole tethered and their anti-inflammatory, quantitative structure-activity relationship, and docking studies. J Heterocycl Chem 58:654–664. https://doi.org/10.1002/jhet.4172
Karimi Askarani H, Iraji A, Rastegari A et al (2020) Design and synthesis of multi-target directed 1,2,3-triazole-dimethylaminoacryloyl-chromenone derivatives with potential use in alzheimer’s disease. BMC Chem 14:1–13. https://doi.org/10.1186/s13065-020-00715-0
Kattimani PP, Somagond SM, Bayannavar PK et al (2020) Novel 5-(1-aryl-1H-pyrazol-3-yl)-1H-tetrazoles as glycogen phosphorylase inhibitors: an in vivo antihyperglycemic activity study. Drug Dev Res 81:70–84. https://doi.org/10.1002/ddr.21606
Kaur K, Kumar V, Gupta GK (2015) Trifluoromethylpyrazoles as anti-inflammatory and antibacterial agents: a review. J Fluor Chem 178:306–326. https://doi.org/10.1016/j.jfluchem.2015.08.015
Kaushik N, Kumar N, Kumar A (2016) Synthesis, antioxidant and antidiabetic activity of 1-[(5-substituted phenyl)-4,5-dihydro-1H-pyrazol-3-yl]- 5-phenyl-1H-tetrazole. Indian J Pharm Sci 78:351–359. https://doi.org/10.4172/pharmaceutical-sciences.1000125
Khadtare N, Stephani R, Korlipara V (2017) Design, synthesis and evaluation of 1,3,6-trisubstituted-4-oxo-1,4-dihydroquinoline-2-carboxylic acid derivatives as ETA receptor selective antagonists using FRET assay. Bioorganic Med Chem Lett 27:2281–2285. https://doi.org/10.1016/j.bmcl.2017.04.049
Khanage SG, Raju A, Mohite PB, Pandhare RB (2013) Analgesic activity of some 1,2, 4-triazole heterocycles clubbed with pyrazole, tetrazole, isoxazole and pyrimidine, Vol 3, pp 13–18. https://doi.org/10.5681/apb.2013.003
Kharb R, Sharma PC, Yar MS (2011) Pharmacological significance of triazole scaffold. J Enzyme Inhib Med Chem 26:1–21. https://doi.org/10.3109/14756360903524304
Kiselev VG, Cheblakov PB, Gritsan NP (2011) Tautomerism and thermal decomposition of tetrazole: high-level ab initio study. J Phys Chem A 115:1743–1753. https://doi.org/10.1021/jp112374t
Kjældgaard AL, Pilely K, Olsen KS et al (2018) Amyotrophic lateral sclerosis: the complement and inflammatory hypothesis. Mol Immunol 102:14–25. https://doi.org/10.1016/j.molimm.2018.06.007
Kumari M, Tahlan S, Narasimhan B et al (2021) Synthesis and biological evaluation of heterocyclic 1,2,4-triazole scaffolds as promising pharmacological agents. BMC Chem 15:1–16. https://doi.org/10.1186/s13065-020-00717-y
Kumbar MN, Kamble RR, Dasappa JP et al (2018) 5-(1-Aryl-3-(thiophen-2-yl)-1H-pyrazol-4-yl)-1H-tetrazoles: Synthesis, structural characterization, Hirshfeld analysis, anti-inflammatory and anti-bacterial studies. J Mol Struct 1160:63–72. https://doi.org/10.1016/j.molstruc.2018.01.047
Kushwaha P, Fatima S, Upadhyay A et al (2019) Synthesis, biological evaluation and molecular dynamic simulations of novel Benzofuran-tetrazole derivatives as potential agents against alzheimer’s disease. Bioorganic Med Chem Lett 29:66–72. https://doi.org/10.1016/j.bmcl.2018.11.005
Lamie PF, Azmey AF (2019) Synthesis and biological evaluation of tetrazole derivatives as TNF-α, IL-6 and COX-2 inhibitors with antimicrobial activity: computational analysis, molecular modeling study and region-specific cyclization using 2D NMR tools. Bioorg Chem 92:103301. https://doi.org/10.1016/j.bioorg.2019.103301
Lamie PF, Philoppes JN, Azouz AA, Safwat NM (2017) Novel tetrazole and cyanamide derivatives as inhibitors of cyclooxygenase-2 enzyme: design, synthesis, anti-inflammatory evaluation, ulcerogenic liability and docking study. J Enzyme Inhib Med Chem 32:805–820. https://doi.org/10.1080/14756366.2017.1326110
Lauretti E, Dincer O, Praticò D (2020) Glycogen synthase kinase-3 signaling in alzheimer’s disease. Biochim Biophys Acta - Mol Cell Res 1867:118664. https://doi.org/10.1016/j.bbamcr.2020.118664
Leal JG, Sauer AC, Mayer JCP et al (2017) Synthesis and electrochemical and antioxidant properties of chalcogenocyanate oxadiazole and 5-heteroarylchalcogenomethyl-1: H -tetrazole derivatives. New J Chem 41:5875–5883. https://doi.org/10.1039/c7nj00920h
Lee HE, Lim D, Lee JY et al (2019) Development of tau-directed small molecule modulators for alzheimer’s disease: a recent patent review (2014–2018). Pharm Pat Anal 8:15–39. https://doi.org/10.4155/ppa-2019-0003
Lenda F, Crouzin N, Cavalier M et al (2011) Synthesis of C5-tetrazole derivatives of 2-amino-adipic acid displaying NMDA glutamate receptor antagonism. Amino Acids 40:913–922. https://doi.org/10.1007/s00726-010-0713-1
Li Q, Yang H, Mo J et al (2018) Identification by shape-based virtual screening and evaluation of new tyrosinase inhibitors. PeerJ 2018:1–14. https://doi.org/10.7717/peerj.4206
Li SM, Tsai SE, Chiang CY et al (2020) New methyl 5-(halomethyl)-1-aryl-1H-1,2,4-triazole-3-carboxylates as selective COX-2 inhibitors and anti-inflammatory agents: design, synthesiss, biological evaluation, and docking study. Bioorg Chem 104:104333. https://doi.org/10.1016/j.bioorg.2020.104333
Liu J, Chang L, Song Y et al (2019) The role of NMDA receptors in alzheimer’s disease. Front Neurosci 13:1–22. https://doi.org/10.3389/fnins.2019.00043
Maria CFD, Bianca de Sousa L, Marisa Ionta RRT (2021) Synthesis of 1,2,3-triazole benzophenone derivatives and evaluation of of in vitro sun protection, antioxidant properties, and antiproliferative activity on HT-144 melanoma cells. J Brazil Chem Soc 32:572–587. https://dx.doi.org/https://doi.org/10.21577/0103-5053.20200211
Malik MA, Wani MY, Al-Thabaiti SA, Shiekh RA (2014) Tetrazoles as carboxylic acid isosteres: chemistry and biology. J Incl Phenom Macrocycl Chem 78:15–37. https://doi.org/10.1007/s10847-013-0334-x
Malik MS, Ahmed SA, Althagafi II et al (2020) Application of triazoles as bioisosteres and linkers in the development of microtubule targeting agents. RSC Med Chem 11:327–348. https://doi.org/10.1039/c9md00458k
Medina M, Avila J (2020) Editorial: untangling the role of tau in physiology and pathology. Front Aging Neurosci 12:10–12. https://doi.org/10.3389/fnagi.2020.00146
Menghereş G, Olajide O, Hemming K (2021) The synthesis and anti-inflammatory evaluation of 1,2,3-triazole linked isoflavone benzodiazepine hybrids. Arkivoc 2020:306–321. https://doi.org/10.24820/ARK.5550190.P011.396
Mittal R, Awasthi SK (2019) Recent advances in the synthesis of 5-substituted 1 H-tetrazoles: a complete survey (2013–2018). Synth 51:3765–3783. https://doi.org/10.1055/s-0037-1611863
Murumkar PR, Chikhale RV (2018) Vicinal diaryl triazoles and tetrazoles. In: Yadav MR, Murumkar RBGPR (eds) Vicinal diaryl substituted heterocycles. Elsevier, pp 191–219
Mushtaq G, Greig NH, Khan JA, Kamal MA (2018) Status of acetylcholinesterase and butyrylcholinesterase in alzheimer’s disease and type 2 diabetes mellitus. CNS Neurol Disord Drug Targets 13:1432–1439. https://doi.org/10.2174/1871527313666141023141545
Najafi Z, Mahdavi M, Saeedi M et al (2019) Novel tacrine-coumarin hybrids linked to 1,2,3-triazole as anti-alzheimer’s compounds: in vitro and in vivo biological evaluation and docking study. Bioorg Chem 83:303–316. https://doi.org/10.1016/j.bioorg.2018.10.056
Navidpour L, Amini M, Shafaroodi H et al (2006) Design and synthesis of new water-soluble tetrazolide derivatives of celecoxib and rofecoxib as selective cyclooxygenase-2 (COX-2) inhibitors. Bioorganic Med Chem Lett 16:4483–4487. https://doi.org/10.1016/j.bmcl.2006.06.032
Neochoritis CG, Zhao T, Dömling A (2019) Tetrazoles via multicomponent reactions. Chem Rev 119:1970–2042. https://doi.org/10.1021/acs.chemrev.8b00564
Nural Y, Ozdemir S, Doluca O et al (2020) Synthesis, biological properties, and acid dissociation constant of novel naphthoquinone–triazole hybrids. Bioorg Chem 105:104441. https://doi.org/10.1016/j.bioorg.2020.104441
Oehlrich D, Peschiulli A, Tresadern G et al (2019) Evaluation of a series of β-secretase 1 inhibitors containing novel heteroaryl-fused-piperazine amidine warheads. ACS Med Chem Lett 10:1159–1165. https://doi.org/10.1021/acsmedchemlett.9b00181
Ornstein PL, Arnold MB, Allen NK et al (1996) Structure-activity studies of 6-(tetrazolylalkyl)-substituted decahydroisoquinoline-3-carboxylic acid AMPA receptor antagonists. 1. Effects of stereochemistry, chain length, and chain substitution. J Med Chem 39:2219–2231. https://doi.org/10.1021/jm950912p
Ostrovskii VA, Popova EA, Trifonov RE (2017) Developments in tetrazole chemistry (2009–16). In: Eric Scriven Christopher Ramsden (ed) Advances in heterocyclic chemistry. Elsevier Ltd., pp 1–62
Özkan H, Demirci B (2019) Synthesis and antimicrobial and antioxidant activities of sulfonamide derivatives containing tetrazole and oxadiazole rings. J Heterocycl Chem 56:2528–2535. https://doi.org/10.1002/jhet.3647
Patouret R, Kamenecka TM (2016) Synthesis of 2-aryl-2H-tetrazoles via a regioselective [3+2] cycloaddition reaction. Tetrahedron Lett 57:1597–1599. https://doi.org/10.1016/j.tetlet.2016.02.102
Paudel S, Min X, Acharya S et al (2017) Triple reuptake inhibitors: design, synthesis and structure–activity relationship of benzylpiperidine–tetrazoles. Bioorganic Med Chem 25:5278–5289. https://doi.org/10.1016/j.bmc.2017.07.046
Paudel S, Acharya S, Yoon G, et al (2017a) Design, synthesis and in vitro activity of 1,4-disubstituted piperazines and piperidines as triple reuptake inhibitors
Popova EA, Trifonov RE (2015) Synthesis and biological properties of amino acids and peptides containing a tetrazolyl moiety. Russ Chem Rev 84:891–916. https://doi.org/10.1070/rcr4527
Praveen kumar K, Prashanthi Y, Rambabu kumar GJSY (2020) Design and synthesis of 2-mercapto benzoxazole coupled benzyl triazoles as anti-inflammatory agents targeting COX-2 enzyme. Asian J Chem 32:3209–3218. https://doi.org/10.14233/ajchem.2020.22956
Ramanathan M, Wang YH, Liu ST (2015) One-Pot Reactions For Synthesis of 2,5-substituted tetrazoles from aryldiazonium salts and amidines. Org Lett 17:5886–5889. https://doi.org/10.1021/acs.orglett.5b03068
Ramsay RR, Albreht A (2018) Kinetics, mechanism, and inhibition of monoamine oxidase. J Neural Transm 125:1659–1683. https://doi.org/10.1007/s00702-018-1861-9
Ranjbar S, Shahvaran P sadat, Edraki N, et al (2020) 1,2,3-Triazole-linked 5-benzylidene (thio)barbiturates as novel tyrosinase inhibitors and free-radical scavengers. Arch Pharm (Weinheim) 353:1–9. https://doi.org/10.1002/ardp.202000058
Redenti S, Marcovich I, De Vita T et al (2019) A triazolotriazine-based dual GSK-3β/CK-1δ ligand as a potential neuroprotective agent presenting two different mechanisms of enzymatic inhibition. ChemMedChem 14:310–314. https://doi.org/10.1002/cmdc.201800778
Ronchi FA, Fernandes AB, Reis RI et al (2016) Synthesis and biological evaluation of novel antihypertensive compounds. Open Chem J 3:56–68. https://doi.org/10.2174/1874842201603010056
Ruiz-Ruiz C, Calzaferri F, García AG (2020) P2x7 receptor antagonism as a potential therapy in amyotrophic lateral sclerosis. Front Mol Neurosci 13:1–13. https://doi.org/10.3389/fnmol.2020.00093
Sağlık BN, Osmaniye D, Acar Çevik U et al (2020) Synthesis, in vitro enzyme activity and molecular docking studies of new benzylamine-sulfonamide derivatives as selective MAO-B inhibitors. J Enzyme Inhib Med Chem 35:1422–1432. https://doi.org/10.1080/14756366.2020.1784892
Sathishkumar S, Kavitha H (2017) Synthesis, characterization and anti-inflammatory evaluation of novel substituted tetrazolodiazepine derivatives. Indian J Chem Sect B 56:732–739
Sepehri N, Mohammadi-Khanaposhtani M, Asemanipoor N, et al (2020) Synthesis, characterization, molecular docking, and biological activities of coumarin–1,2,3-triazole-acetamide hybrid derivatives. Arch Pharm (Weinheim) 353. https://doi.org/10.1002/ardp.202000109
Sharma P, Srivastava P, Seth A et al (2019) Comprehensive review of mechanisms of pathogenesis involved in alzheimer’s disease and potential therapeutic strategies. Prog Neurobiol 174:53–89. https://doi.org/10.1016/j.pneurobio.2018.12.006
Shchegol’kov EV, Makhaeva GF, Boltneva NP, et al (2017) Synthesis, molecular docking, and biological activity of polyfluoroalkyl dihydroazolo[5,1-c][1,2,4]triazines as selective carboxylesterase inhibitors. Bioorganic Med Chem 25:3997–4007. https://doi.org/10.1016/j.bmc.2017.05.045
Shneine JK, Alaraji YH (2016) Chemistry of 1, 2, 4-triazole: a review article. Int J Sci Res 5:1411–1423. https://doi.org/10.21275/v5i3.nov161902
Sooknual P, Pingaew R, Phopin K et al (2020) Synthesis and neuroprotective effects of novel chalcone-triazole hybrids. Bioorg Chem 105:104384. https://doi.org/10.1016/j.bioorg.2020.104384
Sribalan R, Banuppriya G, Kirubavathi M, Padmini V (2019) Synthesis, biological evaluation and in silico studies of tetrazole-heterocycle hybrids. J Mol Struct 1175:577–586. https://doi.org/10.1016/j.molstruc.2018.07.114
Srinivas B, Kumar PV, Nagendra Reddy P et al (2018) Design, synthesis, antioxidant and antibacterial activities of novel 2-((1-Benzyl-1H-1,2,3-Triazol-4-yl)methyl)-5-(2HChromen- 3-yl)-2H-Tetrazoles. Russ J Bioorganic Chem 44:244–251. https://doi.org/10.1134/S1068162018020097
Stotani S, Giordanetto F, Medda F (2016) DYRK1A inhibition as potential treatment for alzheimer’s disease. Future Med Chem 8:681–696. https://doi.org/10.4155/fmc-2016-0013
Subbaiah MAM (2018) Triple reuptake inhibitors as potential therapeutics for depression and other disorders: design paradigm and developmental challenges. J Med Chem 61:2133–2165. https://doi.org/10.1021/acs.jmedchem.6b01827
Sureshkumar K, Maheshwaran V, Dharma Rao T et al (2017) Synthesis, characterization, crystal structure, in-vitro anti-inflammatory and molecular docking studies of 5-mercapto-1-substituted tetrazole incorporated quinoline derivative. J Mol Struct 1146:314–323. https://doi.org/10.1016/j.molstruc.2017.05.085
Sweeney JB, Rattray M, Pugh V, Powell LA (2018) Riluzole-triazole hybrids as novel chemical probes for neuroprotection in amyotrophic lateral sclerosis. ACS Med Chem Lett 9:552–556. https://doi.org/10.1021/acsmedchemlett.8b00103
Tao C, Wang B, Sun L et al (2017) Cu(NO3)2-catalysed direct synthesis of 5-substituted 1H-tetrazoles from alcohols or aldehydes. J Chem Res 41:25–29. https://doi.org/10.3184/174751917X14815427219248
Tratrat C, Haroun M, Paparisva A (2021) New substituted 5-benzylideno-2-adamantylthiazol[3,2- b][1,2,4]triazol-6(5H)ones as possible anti-inflammatory agents. Molecules 26:659. https://doi.org/10.3390/molecules26030659
Tripathi AC, Upadhyay S, Paliwal S, Saraf SK (2018) Privileged scaffolds as MAO inhibitors: retrospect and prospects. Eur J Med Chem 145:445–497. https://doi.org/10.1016/j.ejmech.2018.01.003
Varala R, Babu BH (2018) A click chemistry approach to tetrazoles: recent advances. Mol Docking. https://doi.org/10.5772/intechopen.75720
Vittorio S, Adornato I, Gitto R et al (2020) Rational design of small molecules able to inhibit α-synuclein amyloid aggregation for the treatment of Parkinson’s disease. J Enzyme Inhib Med Chem 35:1727–1735. https://doi.org/10.1080/14756366.2020.1816999
Wang P, Guan PP, Wang T et al (2014) Aggravation of alzheimer’s disease due to the COX-2-mediated reciprocal regulation of IL-1β and Aβ between glial and neuron cells. Aging Cell 13:605–615. https://doi.org/10.1111/acel.12209
Wang S, Liu H, Wang X, et al (2019a) Synthesis and evaluation of anticonvulsant activities of 7-phenyl-4,5,6,7-tetrahydrothieno[3,2-b]pyridine derivatives. Arch Pharm (Weinheim) 352. https://doi.org/10.1002/ardp.201900106
Wang SQ, Wang YF, Xu Z (2019b) Tetrazole hybrids and their antifungal activities. Eur J Med Chem 170:225–234. https://doi.org/10.1016/j.ejmech.2019.03.023
Wei CX, Bian M, Gong GH (2015) Tetrazolium compounds: synthesis and applications in medicine. Molecules 20:5528–5553. https://doi.org/10.3390/molecules20045528
Xie H, Wen H, Zhang D, et al (2017) Designing of dual inhibitors for GSK-3β and CDK5: virtual screening and in vitro biological activities study. Oncotarget 8:18118–18128. https://doi.org/10.18632/oncotarget.15085
Yadav MR, Barmade MA, Chikhale RV MPR (2018) Computational modelling of Kinase inhibitors as anti-alzheimer agents. In: Roy K (ed) Computational modeling of drugs against alzheimer’s disease. Humana Press, New York, pp 341–417
Yan R (2016) Stepping closer to treating alzheimer’s disease patients with BACE1 inhibitor drugs. Transl Neurodegener 5:1–11. https://doi.org/10.1186/s40035-016-0061-5
Yazdani M, Edraki N, Badri R et al (2019) 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. Bioorg Chem 84:363–371. https://doi.org/10.1016/j.bioorg.2018.11.038
Yurttaş L, Kaplancıklı ZA, Temel HE, Çiftçi GA (2017) Novel tetrazole derivatives: synthesis, anticholinesterase activity and cytotoxicity evaluation. Turkish J Biochem 42:169–180. https://doi.org/10.1515/tjb-2016-0207
Zheng B, Lai R, Li J, Zuo Z (2017) Critical role of P2X7 receptors in the neuroinflammation and cognitive dysfunction after surgery. Brain Behav Immun 61:365–374. https://doi.org/10.1016/j.bbi.2017.01.005
Zhou Y, Wang J, Gu Z et al (2016) Next generation of fluorine-containing pharmaceuticals, compounds currently in phase II-III clinical trials of major pharmaceutical companies: new structural trends and therapeutic areas. Chem Rev 116:422–518. https://doi.org/10.1021/acs.chemrev.5b00392
Zhou Q, Phoa AF, Abbassi RH et al (2017) Structural optimization and pharmacological evaluation of inhibitors targeting dual-specificity tyrosine phosphorylation-regulated Kinases (DYRK) and CDC-like kinases (CLK) in glioblastoma. J Med Chem 60:2052–2070. https://doi.org/10.1021/acs.jmedchem.6b01840
Zou Y, Liu L, Liu J, Liu G (2020) Bioisosteres in drug discovery: focus on tetrazole. Future Med Chem 12:91–93. https://doi.org/10.4155/fmc-2019-0288
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2022 The Author(s), under exclusive license to Springer Nature Singapore Pte Ltd.
About this chapter
Cite this chapter
Gupta, P., Sharma, A. (2022). Pharmacological Significance of Triazoles and Tetrazoles in Neurodegenerative Disease: An Overview. In: Ameta, K.L., Kant, R., Penoni, A., Maspero, A., Scapinello, L. (eds) N-Heterocycles. Springer, Singapore. https://doi.org/10.1007/978-981-19-0832-3_10
Download citation
DOI: https://doi.org/10.1007/978-981-19-0832-3_10
Published:
Publisher Name: Springer, Singapore
Print ISBN: 978-981-19-0831-6
Online ISBN: 978-981-19-0832-3
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)