How to cite this paper
Kula, K., Bierczak, P., Miernik, K., Synkiewicz-Musialska, B & Gaurav, G. (2025). Experimental and theoretical correlations in (Z)-C-aryl-N-methylnitrones.Current Chemistry Letters, 14(1), 149-158.
References
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2 Leifert D., and Studer A. (2023) Organic synthesis using nitroxides. Chem. Rev., 123 (16) 10302-10380.
3 Kula K., Dresler E., Demchuk O. M., and Jasiński, R. (2015) New aldimine N-oxides as precursors for preparation of heterocycles with potential biological activity. Przem. Chem., 94 (1) 1385-1387.
4 Merino P. (2005) New developments in nucleophilic additions to nitrones. C. R. Chim., 8 (5) 775-788.
5 Loi N., Hung P., Chinh D., and Phuong, P. (2023) Studying the toxicity and structure-activity relationships of some synthesized polyfunctionalized pyrimidine compounds as potential insecticides. Curr. Chem. Lett., 12 (3) 489-498.
6 Abdel-Raheem S., Drar A., Hussein B., and Moustafa A. (2023) Some oxoimidazolidine and cyanoguanidine compounds: Toxicological efficacy and structure-activity relationships studies. Curr. Chem. Lett., 12 (4) 695-704.
7 Villamena F. A., Das A., and Nash K. M. (2012) Potential implication of the chemical properties and bioactivity of nitrone spin traps for therapeutics. Future Med. Chem., 4 (9) 1171-1207.
8 Janzen E. G. (1971) Spin trapping. Acc. Chem. Res., 4 (1) 31-40.
9 Boyd S. L., and Boyd, R. J. (1994) A theoretical study of spin trapping by nitrone: trapping of hydrogen, methyl, hydroxyl, and peroxyl radicals. J. Phys. Chem., 98 (45) 11705-11713.
10 Novelli G. P., Angiolini P., Tani R., Consales G., and Bordi L. (1986) Phenyl-t-butyl-nitrone is active against traumatic shock in rats. Free Radical Res. Commun., 1 (5) 321-327.
11 Zhao Z., Cheng M., Maples K. R., Ma J. Y., and Buchan A. M. (2001) NXY-059, a novel free radical trapping compound, reduces cortical infarction after permanent focal cerebral ischemia in the rat. Brain Res., 909 (1) 46-50.
12 Doggrell S. A. (2006) Nitrone spin on cerebral ischemia. Curr. Opin. Investig. Drugs., 7 (1) 20-24.
13 Datta P. K., Reddy S., Sharma M., and Lianos E. A. (2006) Differential nephron HO-1 expression following glomerular epithelial cell injury. Nephron. Exp. Nephrol., 103 (4) 131-138.
14 Mandal M. N., Moiseyev G. P., Elliott M. H., Kasus-Jacobi A., Li X., Chen H., Zheng L., Nikolaeva O., Floyd R. A., Ma J. X., and Anderson R. E. (2011) Alpha-phenyl-N-tert-butylnitrone (PBN) prevents light-induced degeneration of the retina by inhibiting RPE65 protein isomerohydrolase activity. J. Biol. Chem., 286 (37) 32491-32501.
15 Willis C. L., and Ray D. E. (2007) Antioxidants attenuate MK-801-induced cortical neurotoxicity in the rat. Neurotoxicology. 28 (1) 161-167.
16 He T., Doblas S., Saunders D., Casteel R., Lerner M., Ritchey J. W., Snider T., Floyd R. A., and Towner, R. A. (2011) Effects of PBN and OKN007 in rodent glioma models assessed by 1H MR spectroscopy. Free Radic. Biol. Med., 51 (2) 490-502.
17 Inoue Y., Asanuma T., Smith N., Saunders D., Oblander J., Kotake Y., Floyd R. A., and Towner, R. A. (2007) Modulation of Fas-FasL related apoptosis by PBN in the early phases of choline deficient diet-mediated hepatocarcinogenesis in rats. Free Radic. Res., 41 (9) 972-980.
18 Zuo L., Chen Y. R., Reyes L. A., Lee H. L., Chen C. L., Villamena F. A., and Zweier, J. L. (2009)
The radical trap 5,5-dimethyl-1-pyrroline N-oxide exerts dose-dependent protection against myocardial ischemia-reperfusion injury through preservation of mitochondrial electron transport. J. Pharmacol. Exp. Ther., 329 (2) 515-523.
19 Yoshii H., Yoshii Y., Asai T., Furukawa T., Takaichi S., and Fujibayashi Y. (2012) Photo-excitation of carotenoids causes cytotoxicity via singlet oxygen production. Biochem. Biophys. Res. Commun., 417 (1) 640-645.
20 Bosnjakovic A., and Schlick S. (2006) Spin trapping by 5,5-dimethylpyrroline-N-oxide in Fenton media in the presence of nafion perfluorinated membranes: limitations and potential. J. Phys. Chem. B., 110 (22) 10720-10728.
21 Ionita P., Conte M., Gilbert B. C., and Chechik V. (2007) Gold nanoparticle-initiated free radical oxidations and halogen abstractions. Org. Biomol. Chem., 5 (21) 3504-3509.
22 Fu H., Zhang L., Zhang S., Zhu Y., and Zhao J. (2006) Electron spin resonance spin-trapping detection of radical intermediates in N-doped TiO2-assisted photodegradation of 4-chlorophenol. J. Phys. Chem. B., 110 (7) 3061-3065.
23 Ríos‐Gutiérrez M., and Domingo L. R. (2019) Unravelling the mysteries of the [3+2] cycloaddition reactions. Eur. J. Org. Chem., 2 267-282.
24 Padwa A., and Bur S. (2016) Asymmetric reactions employing 1,3-dipoles. Chem. Heterocycl. Compd., 52 (9) 616-626.
25 Sirotkina E. V., Efremova M. M. Starova G. L. Kuznetsov M. A., and Molchanov A. P. (2020) Cycloaddition of nitrones to 1,3-diarylpropenones and subsequent transformations of the resulting isoxazolidines. Chem. Heterocycl. Compd., 56 (9) 1193-1201.
26 Sajadikhah S. S., and Didehban K. (2023) Synthesis of substituted isoxazolidines (microreview). Chem. Heterocycl. Compd., 59 (9) 640-642.
27 Yıldırım A. (2020) Diastereoselective thermal [3+2] cycloaddition reactions of nitrone possessing an amide functional group as hydrogen bond donor/acceptor. Chem. Heterocycl. Compd., 56 (3) 365-370.
28 Kula K., and Sadowski M. (2023) Regio-and stereoselectivity of [3+2] cycloaddition reactions between (Z)-1-(anthracen-9-yl)-N-methyl nitrone and analogs of trans-β-nitrostyrene on the basis of MEDT computational study. Chem. Heterocycl. Compd., 59 (3) 138-144.
29 Dresler E., Wróblewska A., and Jasiński R. (2024) Energetic Aspects and Molecular Mechanism of 3-Nitro-substituted 2-Isoxazolines Formation via Nitrile N-Oxide [3+2] Cycloaddition: An MEDT Computational Study. Molecules, 29 (13) 3042.
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31 Taft R. W. (1960) Sigma values from Reactivities1. J. Phys. Chem., 64 (12) 1805-1815.
32 Brown H. C., and Okamoto Y. (1958) Electrophilic substituent constants. J. Am. Chem. Soc., 80 (18) 4979-4987.
33 Exner O. (1966) Studies on the inductive effect. V. Separation of inductive and mesomeric effects in meta and para benzene derivatives. Collect. Czech. Chem. Commun., 31 (1) 65-89.
34 SwissADME. Available online: http://www.swissadme.ch/ (accessed on 12 July 2024).
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38 Tang C., Shao J., Si C., Yang X., Hu X., Li P., and Wang X. (2024) Discovery of indole-3-acetic acid derivatives containing 1,3,4-thiadiazole thioether and amide moieties as novel antibacterial agents. Chem. Heterocycl. Compd., 60 (1/2) 92-98.
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Chem. Rev., 119 (7) 4684-4716.
2 Leifert D., and Studer A. (2023) Organic synthesis using nitroxides. Chem. Rev., 123 (16) 10302-10380.
3 Kula K., Dresler E., Demchuk O. M., and Jasiński, R. (2015) New aldimine N-oxides as precursors for preparation of heterocycles with potential biological activity. Przem. Chem., 94 (1) 1385-1387.
4 Merino P. (2005) New developments in nucleophilic additions to nitrones. C. R. Chim., 8 (5) 775-788.
5 Loi N., Hung P., Chinh D., and Phuong, P. (2023) Studying the toxicity and structure-activity relationships of some synthesized polyfunctionalized pyrimidine compounds as potential insecticides. Curr. Chem. Lett., 12 (3) 489-498.
6 Abdel-Raheem S., Drar A., Hussein B., and Moustafa A. (2023) Some oxoimidazolidine and cyanoguanidine compounds: Toxicological efficacy and structure-activity relationships studies. Curr. Chem. Lett., 12 (4) 695-704.
7 Villamena F. A., Das A., and Nash K. M. (2012) Potential implication of the chemical properties and bioactivity of nitrone spin traps for therapeutics. Future Med. Chem., 4 (9) 1171-1207.
8 Janzen E. G. (1971) Spin trapping. Acc. Chem. Res., 4 (1) 31-40.
9 Boyd S. L., and Boyd, R. J. (1994) A theoretical study of spin trapping by nitrone: trapping of hydrogen, methyl, hydroxyl, and peroxyl radicals. J. Phys. Chem., 98 (45) 11705-11713.
10 Novelli G. P., Angiolini P., Tani R., Consales G., and Bordi L. (1986) Phenyl-t-butyl-nitrone is active against traumatic shock in rats. Free Radical Res. Commun., 1 (5) 321-327.
11 Zhao Z., Cheng M., Maples K. R., Ma J. Y., and Buchan A. M. (2001) NXY-059, a novel free radical trapping compound, reduces cortical infarction after permanent focal cerebral ischemia in the rat. Brain Res., 909 (1) 46-50.
12 Doggrell S. A. (2006) Nitrone spin on cerebral ischemia. Curr. Opin. Investig. Drugs., 7 (1) 20-24.
13 Datta P. K., Reddy S., Sharma M., and Lianos E. A. (2006) Differential nephron HO-1 expression following glomerular epithelial cell injury. Nephron. Exp. Nephrol., 103 (4) 131-138.
14 Mandal M. N., Moiseyev G. P., Elliott M. H., Kasus-Jacobi A., Li X., Chen H., Zheng L., Nikolaeva O., Floyd R. A., Ma J. X., and Anderson R. E. (2011) Alpha-phenyl-N-tert-butylnitrone (PBN) prevents light-induced degeneration of the retina by inhibiting RPE65 protein isomerohydrolase activity. J. Biol. Chem., 286 (37) 32491-32501.
15 Willis C. L., and Ray D. E. (2007) Antioxidants attenuate MK-801-induced cortical neurotoxicity in the rat. Neurotoxicology. 28 (1) 161-167.
16 He T., Doblas S., Saunders D., Casteel R., Lerner M., Ritchey J. W., Snider T., Floyd R. A., and Towner, R. A. (2011) Effects of PBN and OKN007 in rodent glioma models assessed by 1H MR spectroscopy. Free Radic. Biol. Med., 51 (2) 490-502.
17 Inoue Y., Asanuma T., Smith N., Saunders D., Oblander J., Kotake Y., Floyd R. A., and Towner, R. A. (2007) Modulation of Fas-FasL related apoptosis by PBN in the early phases of choline deficient diet-mediated hepatocarcinogenesis in rats. Free Radic. Res., 41 (9) 972-980.
18 Zuo L., Chen Y. R., Reyes L. A., Lee H. L., Chen C. L., Villamena F. A., and Zweier, J. L. (2009)
The radical trap 5,5-dimethyl-1-pyrroline N-oxide exerts dose-dependent protection against myocardial ischemia-reperfusion injury through preservation of mitochondrial electron transport. J. Pharmacol. Exp. Ther., 329 (2) 515-523.
19 Yoshii H., Yoshii Y., Asai T., Furukawa T., Takaichi S., and Fujibayashi Y. (2012) Photo-excitation of carotenoids causes cytotoxicity via singlet oxygen production. Biochem. Biophys. Res. Commun., 417 (1) 640-645.
20 Bosnjakovic A., and Schlick S. (2006) Spin trapping by 5,5-dimethylpyrroline-N-oxide in Fenton media in the presence of nafion perfluorinated membranes: limitations and potential. J. Phys. Chem. B., 110 (22) 10720-10728.
21 Ionita P., Conte M., Gilbert B. C., and Chechik V. (2007) Gold nanoparticle-initiated free radical oxidations and halogen abstractions. Org. Biomol. Chem., 5 (21) 3504-3509.
22 Fu H., Zhang L., Zhang S., Zhu Y., and Zhao J. (2006) Electron spin resonance spin-trapping detection of radical intermediates in N-doped TiO2-assisted photodegradation of 4-chlorophenol. J. Phys. Chem. B., 110 (7) 3061-3065.
23 Ríos‐Gutiérrez M., and Domingo L. R. (2019) Unravelling the mysteries of the [3+2] cycloaddition reactions. Eur. J. Org. Chem., 2 267-282.
24 Padwa A., and Bur S. (2016) Asymmetric reactions employing 1,3-dipoles. Chem. Heterocycl. Compd., 52 (9) 616-626.
25 Sirotkina E. V., Efremova M. M. Starova G. L. Kuznetsov M. A., and Molchanov A. P. (2020) Cycloaddition of nitrones to 1,3-diarylpropenones and subsequent transformations of the resulting isoxazolidines. Chem. Heterocycl. Compd., 56 (9) 1193-1201.
26 Sajadikhah S. S., and Didehban K. (2023) Synthesis of substituted isoxazolidines (microreview). Chem. Heterocycl. Compd., 59 (9) 640-642.
27 Yıldırım A. (2020) Diastereoselective thermal [3+2] cycloaddition reactions of nitrone possessing an amide functional group as hydrogen bond donor/acceptor. Chem. Heterocycl. Compd., 56 (3) 365-370.
28 Kula K., and Sadowski M. (2023) Regio-and stereoselectivity of [3+2] cycloaddition reactions between (Z)-1-(anthracen-9-yl)-N-methyl nitrone and analogs of trans-β-nitrostyrene on the basis of MEDT computational study. Chem. Heterocycl. Compd., 59 (3) 138-144.
29 Dresler E., Wróblewska A., and Jasiński R. (2024) Energetic Aspects and Molecular Mechanism of 3-Nitro-substituted 2-Isoxazolines Formation via Nitrile N-Oxide [3+2] Cycloaddition: An MEDT Computational Study. Molecules, 29 (13) 3042.
30 Hammett L. P. (1937) The effect of structure upon the reactions of organic compounds. Benzene derivatives. J. Am. Chem. Soc., 59 (1) 96-103.
31 Taft R. W. (1960) Sigma values from Reactivities1. J. Phys. Chem., 64 (12) 1805-1815.
32 Brown H. C., and Okamoto Y. (1958) Electrophilic substituent constants. J. Am. Chem. Soc., 80 (18) 4979-4987.
33 Exner O. (1966) Studies on the inductive effect. V. Separation of inductive and mesomeric effects in meta and para benzene derivatives. Collect. Czech. Chem. Commun., 31 (1) 65-89.
34 SwissADME. Available online: http://www.swissadme.ch/ (accessed on 12 July 2024).
35 Lipinski C.A., Lombardo F., Dominy B. W., and Feeney P. J. (2001) Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv. Drug Deliv. Rev., 46 (1) 3-26.
36 PASS Online. Available online: http://www.way2drug.com/passonline/ (accessed on 12 July 2024).
37 Soldaini G., Cardona F., and Goti A. (2007) Catalytic oxidation of imines based on methyltrioxorhenium/urea hydrogen peroxide: A mild and easy chemo-and regioselective entry to nitrones. Org. Lett., 9 (3) 473-476.
38 Tang C., Shao J., Si C., Yang X., Hu X., Li P., and Wang X. (2024) Discovery of indole-3-acetic acid derivatives containing 1,3,4-thiadiazole thioether and amide moieties as novel antibacterial agents. Chem. Heterocycl. Compd., 60 (1/2) 92-98.
39 Mitsui H., Zenki S. I., Shiota T., and Murahashi S. I. (1984) Tungstate catalysed oxidation of secondary amines with hydrogen peroxide. A novel transformation of secondary amines into nitrones. J. Chem. Soc. Chem. Commun., 13 874-875.
40 Izmest’ev A. N., Isakov S. S., Kravchenko A. N., and Gazieva G. A. (2024) The synthesis and antitumor activity of novel 1-alkyl-3-phenyland 3-alkyl-1-phenylimidazothiazolotriazines. Chem. Heterocycl. Compd., 60 (3/4) 133-137.
41 Mohammed J. H., and Salih N. A. M. (2022) Synthesis and characterization of some new nitrones derivatives and screening their biological activities. J. Zhejiang Univ. Sci., 10 (4) 268-273.
42 Gomonov K. A., Pelipko V. V., Litvinov I. A., Baichurin R. I., and Makarenko S. V. (2024) Synthesis and structure of new substituted furan-3-carboxylate hydrazones. Chem. Heterocycl. Compd., 60 (3/4) 196-204.
43 Tikhomolova A. S., Mamleeva Z. V., and Egorova A. Y. (2024) An efficient synthesis of (E)-3-[(dimethylamino) methylidene] furan-2 (3H)-thiones and transamination reactions thereof. Chem. Heterocycl. Compd., 60 (3) 138-142.
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