Electrochemical generation of phenothiazin-5-ium. A sustainable strategy for the synthesis of new bis(phenylsulfonyl)-10H-phenothiazine derivatives.
Journal
Scientific reports
ISSN: 2045-2322
Titre abrégé: Sci Rep
Pays: England
ID NLM: 101563288
Informations de publication
Date de publication:
21 Feb 2024
21 Feb 2024
Historique:
received:
30
10
2023
accepted:
02
02
2024
medline:
22
2
2024
pubmed:
22
2
2024
entrez:
21
2
2024
Statut:
epublish
Résumé
In this work, the electrochemical generation of phenothiazin-5-ium (PTZ
Identifiants
pubmed: 38383682
doi: 10.1038/s41598-024-53620-0
pii: 10.1038/s41598-024-53620-0
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
4276Informations de copyright
© 2024. The Author(s).
Références
Heard, D. M. & Lennox, A. Electrode materials in modern organic electrochemistry. Angew. Chem. Int. Ed. 59, 18866–18884 (2020).
doi: 10.1002/anie.202005745
Leech, M. C. & Lam, K. A. practical guide to electrosynthesis. Nat. Rev. Chem. 6, 275–286 (2022).
pubmed: 37117870
doi: 10.1038/s41570-022-00372-y
Zivari-Moshfegh, F., Khoram, M. M. & Nematollahi, D. Green electrochemical synthesis of silver sulfadiazine microcrystals. RSC Adv. 9, 24105–24109 (2019).
doi: 10.1039/C9RA04504J
Lodarski, K. et al. Discovery of butyrylcholinesterase inhibitors among derivatives of azaphenothiazines. J. Enzyme Inhib. Med. Chem. 30, 98–106 (2015).
pubmed: 24666296
doi: 10.3109/14756366.2014.889127
Pluta, K., Morak-Młodawska, B. & Jeleń, M. Recent progress in biological activities of synthesized phenothiazines. Eur. J. Med. Chem. 46, 3179–3189 (2011).
pubmed: 21620536
doi: 10.1016/j.ejmech.2011.05.013
Jaszczyszyn, A. et al. Chemical structure of phenothiazines and their biological activity. Pharmacol. Rep. 64, 16–23 (2012).
pubmed: 22580516
doi: 10.1016/S1734-1140(12)70726-0
Mentré, F. et al. Dose regimen of favipiravir for Ebola virus disease. Lancet Infect. Dis. 15, 150–151 (2015).
pubmed: 25435054
doi: 10.1016/S1473-3099(14)71047-3
Aktaş, A., Tüzün, B., Aslan, R., Sayin, K. & Ataseven, H. New anti-viral drugs for the treatment of COVID-19 instead of favipiravir. J. Biomol. Struct. Dyn. 39, 7263–7273 (2021).
pubmed: 32783586
doi: 10.1080/07391102.2020.1806112
Jiang, Y., Xu, K. & Zeng, C. Use of electrochemistry in the synthesis of heterocyclic structures. Chem. Rev. 118, 4485–4540 (2017).
pubmed: 29039924
doi: 10.1021/acs.chemrev.7b00271
Mohamadighader, N., Nematollahi, D. & Saraei, M. A. comprehensive study on electrochemical oxidation of phenothiazine in water-acetonitrile mixture: Electrosynthesis of phenothiazine dimers. Electrochim. Acta 425, 140706 (2022).
doi: 10.1016/j.electacta.2022.140706
Scott, K. A. & Njardarson, J. T. Analysis of US FDA-approved drugs containing sulfur atoms. In Sulfur Chemistry 1–34 (Springer, 2019).
Zhou, J. et al. Extended phenothiazines: synthesis, photophysical and redox properties, and efficient photocatalytic oxidative coupling of amines. Chem. Sci. 13, 5252–5260 (2022).
pubmed: 35655566
pmcid: 9093200
doi: 10.1039/D2SC01086K
Padhy, H. J. et al. Synthesis and applications of low-bandgap conjugated polymers containing phenothiazine donor and various benzodiazole acceptors for polymer solar cells. J. Polym. Sci. Part A Polym. Chem. 48, 4823–4834 (2010).
doi: 10.1002/pola.24273
Ullah, A. et al. Novel phenothiazine-based self-assembled monolayer as a hole selective contact for highly efficient and stable p-i-n perovskite solar cells. Adv. Energy Mater. 12, 2103175 (2022).
doi: 10.1002/aenm.202103175
Tozkoparan, B., Küpeli, E., Yeşilada, E. & Ertan, M. Preparation of 5-aryl-3-alkylthio-l,2,4-triazoles and corresponding sulfones with antiinflammatory–analgesic activity. Bioorganic Med. Chem. Lett. 15, 1808–1814 (2007).
doi: 10.1016/j.bmc.2006.11.029
Hwang, S. H. et al. Synthesis and structure–activity relationship studies of urea-containing pyrazoles as dual inhibitors of cyclooxygenase-2 and soluble epoxide hydrolase. J. Med. Chem. 54, 3037–3050 (2011).
pubmed: 21434686
pmcid: 3281519
doi: 10.1021/jm2001376
Kudryavtsev, K. V., Bentley, M. L. & McCafferty, D. G. Probing of the cis-5-phenyl proline scaffold as a platform for the synthesis of mechanism-based inhibitors of the Staphylococcus aureus sortase SrtA isoform. Bioorganic Med. Chem. Lett. 17, 2886–2893 (2009).
doi: 10.1016/j.bmc.2009.02.008
Guruswamy, B., Arul, R. K., Chaitan, M. V. S. R. K. & Darsi, S. S. P. K. Synthesis and biological evaluation of novel β-hydroxy benzimidazolyl sulfone fluoroquinolones by selective oxidation using ammonium molybdate catalysed H
doi: 10.5155/eurjchem.4.4.329-335.792
Al-Said, M. S., Ghorab, M. M. & Nissan, Y. M. Dapson in heterocyclic chemistry, part VIII: Synthesis, molecular docking and anticancer activity of some novel sulfonylbiscompounds carrying biologically active 1,3-dihydropyridine, chromene and chromenopyridine moieties. Chem. Cent. J. 6, 1–14 (2012).
doi: 10.1186/1752-153X-6-64
Kamble, R. B., Chavan, S. S. & Suryavanshi, G. An efficient heterogeneous copper fluorapatite (CuFAP)-catalysed oxidative synthesis of diaryl sulfone under mild ligand-and base-free conditions. N. J. Chem. 43, 1632–1636 (2019).
doi: 10.1039/C8NJ04845B
Anderson, R., Groundwater, P. W., Todd, A. & Worsley, A. Antibacterial Agents: Chemistry, Mode of Action, Mechanisms of Resistance and Clinical Applications (John Wiley & Sons, 2012).
doi: 10.1002/9781118325421
Shoaib Ahmad Shah, S., Rivera, G. & Ashfaq, M. Recent advances in medicinal chemistry of sulfonamides. Rational design as anti-tumoral, anti-bacterial and anti-inflammatory agents. Mini Rev. Med. Chem. 13, 70–86 (2013).
doi: 10.2174/138955713804484749
Scozzafava, A., Owa, T., Mastrolorenzo, A. & Supuran, C. T. Anticancer and antiviral sulfonamides. Curr. Med. Chem. 10, 925–953 (2003).
pubmed: 12678681
doi: 10.2174/0929867033457647
Supuran, C. T., Casini, A. & Scozzafava, A. Protease inhibitors of the sulfonamide type: Anticancer, antiinflammatory, and antiviral agents. Med. Res. Rev. 23, 535–558 (2003).
pubmed: 12789686
doi: 10.1002/med.10047
Rakesh, K. P. et al. Recent development of sulfonyl or sulfonamide hybrids as potential anticancer agents. Med. Chem. 18, 488–505 (2018).
Pant, S. M. et al. Design, synthesis, and testing of potent, selective hepsin inhibitors via application of an automated closed-loop optimization platform. J. Med. Chem. 61, 4335–4347 (2018).
pubmed: 29701962
doi: 10.1021/acs.jmedchem.7b01698
Nishioka, H., Tooi, N., Isobe, T., Nakatsuji, N. & Aiba, K. BMS-708163 and Nilotinib restore synaptic dysfunction in human embryonic stem cell-derived Alzheimer’s disease models. Sci. Rep. 6, 33427 (2016).
pubmed: 27641902
pmcid: 5027582
doi: 10.1038/srep33427
Pennington, L. D. et al. Discovery and structure-guided optimization of diarylmethanesulfonamide disrupters of glucokinase–glucokinase regulatory protein (GK–GKRP) binding: Strategic use of a N→ S (nN→ σ* S-X) interaction for conformational constraint. J. Med. Chem. 58, 9663–9679 (2015).
pubmed: 26551034
doi: 10.1021/acs.jmedchem.5b01367
Gillman, K. W. et al. Discovery and evaluation of BMS-708163, a potent, selective and orally bioavailable γ-secretase inhibitor. ACS Med. Chem. Lett. 1, 120–124 (2010).
pubmed: 24900185
pmcid: 4007960
doi: 10.1021/ml1000239
Sugimoto, H. et al. An orally bioavailable small molecule antagonist of CRTH2, ramatroban (BAY u3405), inhibits prostaglandin D2-induced eosinophil migration in vitro. J. Pharmacol. Exp. Ther. 305, 347–352 (2003).
pubmed: 12649388
doi: 10.1124/jpet.102.046748
Lafferty, J. J., Garvey, E., Nodiff, E. A., Thompson, W. E. & Zirkle, C. L. The synthesis of phenothiazines. VII. Methyl- and arylsulfonylation of phenothiazine and its 10-substituted derivatives. J. Org. Chem. 27, 1346–1351 (1962).
doi: 10.1021/jo01051a052
Bard, A. J. & Faulkner, L. R. Electrochemical Methods: Fundamentals and Applications (Wiley, 2001).
Nematollahi, D., Joudaki, M., Khazalpour, S. & Pouladi, F. Electrochemical oxidation of sulfinic acids: Efficient oxidative synthesis of diaryl disulfones. J. Electrochem. Soc. 164, G65–G70 (2017).
doi: 10.1149/2.1111706jes
Zivari-Moshfegh, F., Javanmardi, F. & Nematollahi, D. A comprehensive electrochemical study on anti-tuberculosis drug rifampicin. Investigating reactions of rifampicin-quinone with other anti-tuberculosis drugs, isoniazid, pyrazinamide and ethambutol. Electrochim. Acta 457, 142487 (2023).
doi: 10.1016/j.electacta.2023.142487
Zivari-Moshfegh, F. & Nematollahi, D. An eco-friendly electrochemical process for the formation of a new desloratadine derivative and its antibacterial susceptibility. Report of a new type of ortho-quinhydrone complex. Electrochim. Acta 421, 140518 (2022).
doi: 10.1016/j.electacta.2022.140518
Zivari-Moshfegh, F. & Nematollahi, D. New insights into co-administration of anti-tuberculosis drug rifampicin with acetaminophen and vitamin C: Strong electrochemical evidence for the detoxification. J. Electrochem. Soc. 170, 095501 (2023).
doi: 10.1149/1945-7111/acf95c
Varmaghani, F., Nematollahi, D., Mallakpour, S. & Esmaili, R. Electrochemical oxidation of 4-substituted urazoles in the presence of arylsulfinic acids: An efficient method for the synthesis of new sulfonamide derivatives. Green Chem. 14, 963–967 (2012).
doi: 10.1039/c2gc16342j
Varmaghani, F. & Nematollahi, D. Electrochemical study of 1,2-dihydropyridazine-3,6-dione in protic and aprotic solvents: Oxidative ring cleavage and reduction. Electrochim. Acta 56, 6089–6096 (2011).
doi: 10.1016/j.electacta.2011.04.076
Salehzadeh, H., Nematollahi, D. & Rafiee, M. Electrochemical dimerization of 4-methylesculetin: Synthesis and kinetic study of a highly-oxygenated dimer. J. Electroanal. Chem. 650, 226–232 (2011).
doi: 10.1016/j.jelechem.2010.09.019
Shahparast, S., Nematollahi, D., Sharafi-Kolkeshvandi, M. & Goljani, H. Direct electrochemical dimerization of N, N′-diphenylbenzidine. J. Electrochem. Soc. 166, G47 (2019).
doi: 10.1149/2.0081908jes
Nematollahi, D., Shayani-Jam, H., Alimoradi, M. & Niroomand, S. Electrochemical oxidation of acetaminophen in aqueous solutions: Kinetic evaluation of hydrolysis, hydroxylation and dimerization processes. Electrochim. Acta 54, 7407–7415 (2009).
doi: 10.1016/j.electacta.2009.07.077
Souri, Z., Masoudi Khoram, M., Nematollahi, D., Mazloum-Ardakani, M. & Alizadeh, H. A. green protocol for the electrochemical synthesis of a fluorescent dye with antibacterial activity from imipramine oxidation. Sci. Rep. 12, 4921 (2022).
pubmed: 35318352
pmcid: 8941072
doi: 10.1038/s41598-022-08770-4
Beiginejad, H. & Nematollahi, D. Electrochemical oxidation of 2, 5-diethoxy-4-morpholinoaniline in aqueous solutions. Electrochim. Acta 114, 242–250 (2013).
doi: 10.1016/j.electacta.2013.09.063
Beiginejad, H., Nematollahi, D., Varmaghani, F. & Bayat, M. Efficient factors on the hydrolysis reaction rate of some para-aminophenol derivatives in acidic pHs. J. Electrochem. Soc. 160, H469 (2013).
doi: 10.1149/2.084308jes
Blankert, B. et al. Electrochemical, chemical and enzymatic oxidations of phenothiazines. Electroanalysis 17, 1501–1510 (2005).
doi: 10.1002/elan.200403253
Zhang, C., Liu, J. & Chen, B. Effect of CeO
doi: 10.1016/j.ceramint.2018.07.227
Jamshidi, M., Nematollahi, D., Bayat, M. & Salahifar, E. Unsymmetrical diaryl sulfones through electrochemical oxidation of fast violet B in the presence of aryl sulfinic acids. J. Electrochem. Soc. 163, G211–G218 (2016).
doi: 10.1149/2.1431614jes