Revealing the role of the benzyloxy pharmacophore in the design of a new class of monoamine oxidase-B inhibitors.

Chromones / pharmacology Coumarins Dopamine Agents Monoamine Oxidase / metabolism Monoamine Oxidase Inhibitors / pharmacology Structure-Activity Relationship
MAO-A MAO-B benzyloxy pharmacophore neurological disorders structure-activity relationships

Journal

Archiv der Pharmazie
ISSN: 1521-4184
Titre abrégé: Arch Pharm (Weinheim)
Pays: Germany
ID NLM: 0330167

Informations de publication

Date de publication:
Aug 2022
Historique:
revised: 11 04 2022
received: 15 02 2022
accepted: 14 04 2022
pubmed: 15 5 2022
medline: 3 8 2022
entrez: 14 5 2022
Statut: ppublish

Résumé

The conceptual layout of monoamine oxidase (MAO) inhibitors has been modified to explore their potential biological application in the case of neurological disorders for the time being. The current review article is an effort to display the summation of innovative conceptual prospects of MAO inhibitors and their intriguing chemistry and bioactivity. Based on this scenario, we emphasize the pivotal role of the benzyloxy moiety attached to scaffolds like oxadiazolones, indolalkylamines, safinamide, caffeine, benzofurans, α-tetralones, β-nitrostyrene, benzoquinones, coumarins, indoles, chromones, and chromanone analogs, while acting as an MAO inhibitor.

Identifiants

DOI: 10.1002/ardp.202200084 PMID: 35567313
pubmed: 35567313
doi: 10.1002/ardp.202200084
doi:

Substances chimiques

Chromones 0
Coumarins 0
Dopamine Agents 0
Monoamine Oxidase Inhibitors 0
Monoamine Oxidase EC 1.4.3.4

Types de publication

Journal Article Review

Langues

eng

Sous-ensembles de citation

IM

Pagination

e2200084

Subventions

Organisme : Research Center for Advanced Materials Science
ID : R.G.P.1/33/43.

Informations de copyright

© 2022 Deutsche Pharmazeutische Gesellschaft.

Références

C. Marogianni, M. Sokratous, E. Dardiotis, G. M. Hadjigeorgiou, D. Bogdanos, G. Xiromerisiou, Int. J. Mol. Sci. 2020, 21, 8421. https://doi.org/10.3390/ijms21228421
M. T. Heneka, M. J. Carson, J. el Khoury, E. Gary, F. Brosseron, D. L. Feinstein, A. H. Jacobs, T. Wyss-Coray, J. Vitorica, R. M. Ransohoff, Lancet Neurol. 2018, 14​.
D. G. T. Parambi, K. S. Alharbi, R. Kumar, S. Harilal, G.E.-S. Batiha, N. Cruz-Martins, O. Magdy, A. Musa, D. S. Panda, B. Mathew, Mol. Neurobiol. 2022, 59, 191. https://doi.org/10.1007/s12035-021-02555-y
M. Singh, S. P. Singh, D. Yadav, M. Agarwal, S. Agarwal, V. Agarwal, G. Swargiary, S. Srivastava, S. Tyagi, R. Kaur, S. Mani, Curr. Gene Ther. 2021, 21, 23. https://doi.org/10.2174/1566523220999200817164907
N. Puranik, D. Yadav, P. S. Chauhan, M. Kwak, J.-O. Jin, Curr. Gene Ther. 2021, 21, 11. https://doi.org/10.2174/1566523220999200917114101
W. J. Geldenhuys, C. J. Van der Schyf, Curr. Med. Chem. 2013, 20, 1662. https://doi.org/10.2174/09298673113209990112
B. Mathew, S. Carradori, P. Guglielmi, M.dS. Uddin, H. Kim, Curr. Med. Chem. 2020, 28, 266. https://doi.org/10.2174/0929867327666200121165931
P. O. Patil, S. B. Bari, S. D. Firke, P. K. Deshmukh, S. T. Donda, D. A. Patil, Bioorg. Med. Chem. 2013, 21, 2434. https://doi.org/10.1016/j.bmc.2013.02.017
D. Viña, M. J. Matos, G. Ferino, E. Cadoni, R. Laguna, F. Borges, E. Uriarte, L. Santana, ChemMedChem 2012, 7, 464. https://doi.org/10.1002/cmdc.201100538
J. C. Shih, K. Chen, M. J. Ridd, Annu. Rev. Neurosci. 1999, 22, 197. https://doi.org/10.1146/annurev.neuro.22.1.197
L. Dezsi, L. Vecsei, CNS Neurol. Disord Drug Targets. 2017, 16, 425. https://doi.org/10.2174/1871527316666170124165222
P. Guglielmi, B. Mathew, D. Secci, S. Carradori, Eur. J. Med. Chem. 2020, 205, 112650. https://doi.org/10.1016/j.ejmech.2020.112650
Y. J. Rao, K. Abhijit, G. Mallikarjun, Y. Hemasri, Chem. Pap. 2021, 75, 703. https://doi.org/10.1007/s11696-020-01332-w
A. Bolasco, S. Carradori, R. Fioravanti, Expert Opin. Ther. Pat. 2010, 20, 909. https://doi.org/10.1517/13543776.2010.495716
S. Gal, Z. A. Abassi, M. B. H. Youdim, Neurotox. Res. 2010, 18, 143. https://doi.org/10.1007/s12640-009-9128-8
V. P. Vishal, J. M. Oh, A. Khames, M. A. Abdelgawad, A. S. Nair, L. R. Nath, N. Gambacorta, F. Ciriaco, O. Nicolotti, H. Kim, B. Mathew, Pharmaceutics 2021, 13, 850. https://doi.org/10.3390/pharmaceutics13060850
A. Helguera, G. Perez-Machado, M. D. S. Cordeiro, F. Borges, Mini Rev. Med. Chem. 2012, 12, 907. https://doi.org/10.2174/138955712802762301
M. Naoi, W. Maruyama, K. Inaba-Hasegawa, Curr. Top. Med. Chem. 2013, 12, 2177. https://doi.org/10.2174/1568026611212200006
D. Muck-Seler, P. Presecki, N. Mimica, M. Mustapic, N. Pivac, A. Babic, G. Nedic, V. Folnegovic-Smalc, Prog. Neuro Psychopharmacol. Biol. Psychiatry 2009, 33, 1226. https://doi.org/10.1016/j.pnpbp.2009.07.004
N. Mimica, D. Mück-Seler, N. Pivac, M. Mustapić, M. Dezeljin, T. Stipcević, P. Presecki, E. Radonić, V. Folnegović-Smalc, Coll. Antropol. 2008, 32(Suppl. 1), 119.
C. Binda, P. Newton-Vinson, F. Hubálek, D. E. Edmondson, A. Mattevi, Nat. Struct. Biol. 2002, 9, 22. https://doi.org/10.1038/nsb732
L. de Colibus, M. Li, C. Binda, A. Lustig, D. E. Edmondson, A. Mattevi, Proc. Natl. Acad. Sci. USA. 2005, 102, 12684. https://doi.org/10.1073/pnas.0505975102
D. Knez, M. Sova, U. Košak, S. Gobec, Future Med. Chem. 2017, 9, 811. https://doi.org/10.4155/fmc-2017-0036
S. J. Cloete, C. I. N'Da, L. J. Legoabe, A. Petzer, J. P. Petzer, Mol. Divers. 2021, 25, 491. https://doi.org/10.1007/s11030-020-10143-w
M. Joao Matos, D. Vina, S. Vazquez-Rodriguez, E. Uriarte, L. Santana, Curr. Top. Med. Chem. 2013, 12, 2210. https://doi.org/10.2174/1568026611212200008
S. Carradori, R. Silvestri, J. Med. Chem. 2015, 58, 6717. https://doi.org/10.1021/jm501690r
I. Engelbrecht, J. P. Petzer, A. Petzer, Bioorg. Med. Chem. Lett. 2015, 25, 1896. https://doi.org/10.1016/j.bmcl.2015.03.040
J. P. M. Finberg, J. M. Rabey, Front. Pharmacol. 2016, 7, 340. https://doi.org/10.3389/fphar.2016.00340
B. Strydom, J. J. Bergh, J. P. Petzer, Bioorg. Med. Chem. Lett. 2013, 23, 1269. https://doi.org/10.1016/j.bmcl.2013.01.003
A. S. Nair, J.-M. Oh, V. P. Koyiparambath, S. Kumar, S. T. Sudevan, O. Soremekun, M. E. Soliman, A. Khames, M. A. Abdelgawad, L. K. Pappachen, B. Mathew, H. Kim, Molecules 2021, 26, 3264. https://doi.org/10.3390/molecules26113264
S. H. Seong, M. Y. Ali, H. A. Jung, J. S. Choi, Bioorg. Chem. 2019, 92, 103293. https://doi.org/10.1016/j.bioorg.2019.103293
P. Guglielmi, S. Carradori, A. Ammazzalorso, D. Secci, Drug Discov. 2019, 14, 995. https://doi.org/10.1080/17460441.2019.1637415
B. Kumar, S. Sheetal, A. K. Mantha, V. Kumar, RSC Adv. 2016, 6, 42660. https://doi.org/10.1039/C6RA00302H
T. Müller, Neurodegener. Dis. Manag. 2020, 10, 195. https://doi.org/10.2217/nmt-2020-0017
M. Rullo, M. Catto, A. Carrieri, M. de Candia, C. D. Altomare, L. Pisani, Molecules 2019, 24, 4507. https://doi.org/10.3390/molecules24244507
P. L. Chazot, C.urr Opin, Investig. Drugs 2007, 8, 570.
Z. Wang, J. Wu, X. Yang, P. Cai, Q. Liu, K. D. G. Wang, L. Kong, X. Wang, Bioorg. Med. Chem. 2016, 24, 5929. https://doi.org/10.1016/j.bmc.2016.09.050
S. K. Yeon, J. W. Choi, J.-H. Park, Y. R. Lee, H. J. Kim, S. J. Shin, B. K. Jang, S. Kim, Y.-S. Bahn, G. Han, Y. S. Lee, A. N. Pae, K. D. Park, Bioorg. Med. Chem. 2018, 26, 232. https://doi.org/10.1016/j.bmc.2017.11.036
C. Binda, J. Wang, L. Pisani, C. Caccia, A. Carotti, P. Salvati, D. E. Edmondson, A. Mattevi, J. Med. Chem. 2007, 50, 5848. https://doi.org/10.1021/jm070677y
F. Mazouz, S. Gueddari, C. Burstein, D. Mansuy, R. Milcent, J. Med. Chem. 1993, 36, 1157. https://doi.org/10.1021/jm00061a006
S. Bernard, C. Fuseau, L. Schmid, R. Milcent, C. Crouzel, Eur. J. Nucl. Med. 1996, 23, 150. https://doi.org/10.1007/BF01731838
M. Hirata, S. Kagawa, M. Yoshimoto, Y. Ohmomo, Chem. Pharm. Bull. 2002, 50, 609. https://doi.org/10.1248/cpb.50.609
M. Yoshimoto, M. Hirata, S. Kagawa, Y. Magata, Y. Ohmomo, T. Temma, J. Label. Compd. Radiopharm. 2019, 62, 580. https://doi.org/10.1002/jlcr.3779
V. Pérez, J. L. Marco, E. Fernández-Álvarez, M. Unzeta, B.rJ. Pharmacol, Br. J. Pharmacol. 1999, 127, 869. https://doi.org/10.1038/sj.bjp.0702600
V. Perez, M. Unzeta, Neurochem. Int. 2003, 42, 221. https://doi.org/10.1016/S0197-0186(02)00091-8
V. Perez, M. Romera, J. M. Lizcano, J. L. Marco, M. Unzeta, J. Pharm. Pharmacol. 2010, 55, 713. https://doi.org/10.1211/002235703765344649
E. Sanz, M. Romera, L. Bellik, J. I. Marco, M. Unzeta, Med. Sci. Monit Int. Med. J. Exp. Clin. Res. 2004, 10, BR477-84.
V. Battaglia, E. Sanz, M. Salvi, M. Unzeta, A. Toninello, Cell. Mol. Life Sci. 2006, 63, 1440. https://doi.org/10.1007/s00018-006-6105-8
E. Sanz, A. Quintana, J. Hidalgo, J. L. Marco, M. Unzeta, Mol. Cell. Neurosci. 2009, 41, 19. https://doi.org/10.1016/j.mcn.2009.01.005
I. Bolea, J. Juárez-Jiménez, de C. los, M. Rı́os, R. Chioua, F. J. Pouplana, M. Luque, J. Unzeta, A. Marco-Contelles, J. Med. Chem. 2011, 54, 8251. https://doi.org/10.1021/jm200853t
R. Purgatorio, N. Gambacorta, M. Catto, de M. Candia, L. Pisani, A. Espargaró, R. Sabaté, S. Cellamare, O. Nicolotti, C. D. Altomare, Molecules 2020, 25, 5773. https://doi.org/10.3390/molecules25235773
I. Bolea, M. A. Colivicchi, C. Ballini, J. Marco-Contelles, K. F. Tipton, M. Unzeta, L. della Corte, CNS Neurosci. Ther. 2014, 20, 641. https://doi.org/10.1111/cns.12271
F. Leonetti, C. Capaldi, L. Pisani, O. Nicolotti, G. Muncipinto, A. Stefanachi, S. Cellamare, C. Caccia, A. Carotti, J. Med. Chem. 2007, 50, 4909. https://doi.org/10.1021/jm070725e
F. Chimenti, D. Secci, A. Bolasco, P. Chimenti, B. Bizzarri, A. Granese, S. Carradori, M. Yáñez, F. Orallo, F. Ortuso, S. Alcaro, J. Med. Chem. 2009, 52, 1935. https://doi.org/10.1021/jm801496u
L. Pisani, G. Muncipinto, T. F. Miscioscia, O. Nicolotti, F. Leonetti, M. Catto, C. Caccia, P. Salvati, R. Soto-Otero, E. Mendez-Alvarez, C. Passeleu, A. Carotti, J. Med. Chem. 2009, 52, 6685. https://doi.org/10.1021/jm9010127
L. Pisani, M. Catto, O. Nicolotti, G. Grossi, M. di Braccio, R. Soto-Otero, E. Mendez-Alvarez, A. Stefanachi, D. Gadaleta, A. Carotti, Eur. J. Med. Chem. 2013, 70, 723. https://doi.org/10.1016/j.ejmech.2013.09.034
L. Pisani, R. Farina, O. Nicolotti, D. Gadaleta, R. Soto-Otero, M. Catto, M. di Braccio, E. Mendez-Alvarez, A. Carotti, Eur. J. Med. Chem. 2015, 89, 98. https://doi.org/10.1016/j.ejmech.2014.10.029
J. Joubert, G. B. Foka, B. P. Repsold, D. W. Oliver, E. Kapp, S. F. Malan, Eur. J. Med 2017, 125, 853. https://doi.org/10.1016/j.ejmech.2016.09.041
A. A. Titov, M. S. Kobzev, M. Catto, M. de Candia, N. Gambacorta, N. Denora, L. Pisani, O. Nicolotti, T. N. Borisova, A.V Varlamov, L. G. Voskressensky, C. D. Altomare, ACS Chem. Neurosci. 2021, 12, 340. https://doi.org/10.1021/acschemneuro.0c00706
B. Strydom, S. F. Malan, N. Castagnoli, J. J. Bergh, J. P. Petzer, Bioorg. Med. Chem. 2010, 18, 1018. https://doi.org/10.1016/j.bmc.2009.12.064
H. P. Booysen, C. Moraal, G. Terre'Blanche, A. Petzer, J. J. Bergh, J. P. Petzer, Bioorg. Med. Chem. 2011, 19, 7507. https://doi.org/10.1016/j.bmc.2011.10.036
L. J. Legoabe, A. Petzer, J. P. Petzer, Bioorg. Med. Chem. Lett. 2012, 22, 5480. https://doi.org/10.1016/j.bmcl.2012.07.025
L. J. Legoabe, A. Petzer, J. P. Petzer, Bioorg. Chem. 2012, 45, 1. https://doi.org/10.1016/j.bioorg.2012.08.003
L. Pisani, M. Barletta, R. Soto-Otero, O. Nicolotti, E. Mendez-Alvarez, M. Catto, A. Introcaso, A. Stefanachi, S. Cellamare, C. Altomare, A. Carotti, J. Med. Chem 2013, 56, 2651. https://doi.org/10.1021/jm4000769
L. Meiring, J. P. Petzer, A. Petzer, Bioorg. Med. Chem. Lett. 2013, 23, 5498. https://doi.org/10.1016/j.bmcl.2013.08.071
L. J. Legoabe, A. Petzer, J. P. Petzer, Bioorg. Med. Chem. Lett. 2014, 24, 2758. https://doi.org/10.1016/j.bmcl.2014.04.021
L. Legoabe, J. Petzer, A. Petzer, Drug Des. Dev. Ther. 2015, 9, 3635. https://doi.org/10.2147/DDDT.S86225
M. M. van der Walt, G. Terre'Blanche, J. P. Petzer, A. Petzer, Eur. J. Med. Chem. 2017, 125, 1193. https://doi.org/10.1016/j.ejmech.2016.11.016
S. Mostert, A. Petzer, J. P. Petzer, Eur. J. Med. Chem. 2017, 135, 196. https://doi.org/10.1016/j.ejmech.2017.04.055
J.-S. Lan, T. Zhang, Y. Liu, Y. Zhang, J. Hou, S.-S. Xie, J. Yang, Y. Ding, Z. Cai, MedChemComm 2017, 8, 471. https://doi.org/10.1039/C6MD00586A
G. S. Jeong, S. Kaipakasseri, S. R. Lee, N. Marraiki, G. E. Batiha, S. Dev, A. Palakkathondi, F. S. Kavully, N. Gambacorta, O. Nicolotti, B. Mathew, H. Kim, ChemMedChem 2020, 15, 2257. https://doi.org/10.1002/cmdc.202000491

Auteurs

Sachithra T Sudevan (ST)

Department of Pharmaceutical Chemistry, Amrita School of Pharmacy, Amrita Vishwa Vidyapeetham, AIMS Health Sciences Campus, Kochi, India.

T M Rangarajan (TM)

Department of Chemistry, Sri Venketeswara College, University of Delhi, New Delhi, India.

Abdullah G Al-Sehemi (AG)

Research Center for Advanced Materials Science, King Khalid University, Abha, Saudi Arabia.
Department of Chemistry, KingKhalid University, 61413, Abha, Saudi Arabia.

Aathira S Nair (AS)

Department of Pharmaceutical Chemistry, Amrita School of Pharmacy, Amrita Vishwa Vidyapeetham, AIMS Health Sciences Campus, Kochi, India.

Vishal P Koyiparambath (VP)

Department of Pharmaceutical Chemistry, Amrita School of Pharmacy, Amrita Vishwa Vidyapeetham, AIMS Health Sciences Campus, Kochi, India.

Bijo Mathew (B)

Department of Pharmaceutical Chemistry, Amrita School of Pharmacy, Amrita Vishwa Vidyapeetham, AIMS Health Sciences Campus, Kochi, India.
ORCID: 0000-0002-6658-4497

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Classifications MeSH

questionsmedicales.fr › Composés hétérocycliques › Composés hétérocycliques à cycles fusionnés › Composés hétérobicycliques › Benzopyranes › 4H-1-Benzopyran-4-ones › Revealing the role of the benzyloxy...
questionsmedicales.fr › Composés hétérocycliques › Composés hétérocycliques à cycles fusionnés › Composés hétérobicycliques › Benzopyranes › Coumarines › Revealing the role of the benzyloxy...
questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Effets physiologiques des médicaments › Agents neuromédiateurs › Agents dopaminergiques › Revealing the role of the benzyloxy...
questionsmedicales.fr › Enzymes et coenzymes › Enzymes › Oxidoreductases › Oxidoreductases acting on CH-NH2 group donors › Monoamine oxidase › Revealing the role of the benzyloxy...
questionsmedicales.fr › Actions chimiques et utilisations › Actions pharmacologiques › Mécanismes moléculaires de l'action pharmacologique › Antienzymes › Inhibiteurs de la monoamine oxydase › Revealing the role of the benzyloxy...
questionsmedicales.fr › Phénomènes physiologiques › Phénomènes pharmacologiques et toxicologiques › Phénomènes pharmacologiques › Relation structure-activité › Revealing the role of the benzyloxy...