A Mild and Versatile Friedel-Crafts Methodology for the Diversity-Oriented Synthesis of Redox-Active 3-Benzoylmenadiones with Tunable Redox Potentials.
Friedel-Crafts reaction
acylation
acyltrifluoroacetate
benzoyl
electrochemistry
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
ISSN: 1521-3765
Titre abrégé: Chemistry
Pays: Germany
ID NLM: 9513783
Informations de publication
Date de publication:
12 Mar 2020
12 Mar 2020
Historique:
received:
13
09
2019
revised:
04
11
2019
pubmed:
21
11
2019
medline:
21
11
2019
entrez:
21
11
2019
Statut:
ppublish
Résumé
A series of highly diversified 3-aroylmenadiones was prepared by a new Friedel-Crafts acylation variant/oxidative demethylation strategy. A mild and versatile acylation was performed between 1,4-dimethoxy-2-methylnaphthalene and various activated/deactivated benzoic and heteroaromatic carboxylic acids, in the presence of mixed trifluoroacetic anhydride and triflic acid, at room temperature and in air. The 1,4-dimethoxy-2-methylnaphthalene-derived benzophenones were isolated in high yield, and submitted to oxidative demethylation with cerium ammonium nitrate to produce 3-benzoylmenadiones. All 1,4-naphthoquinone derivatives were investigated as redox-active electrophores by cyclic voltammetry. The electrochemical data recorded for 3-acylated menadiones are characterized by a second redox process, the potentials of which cover a wide range of values (500 mV). These data emphasize the ability of the generated structural diversity at the 3-aroyl chain of these electrophores to fine-tune their corresponding redox potentials. These properties are of significance in the context of antimalarial drug development and understanding of the mechanism of bioactivation/action.
Identifiants
pubmed: 31746499
doi: 10.1002/chem.201904220
doi:
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
3314-3325Subventions
Organisme : Agence Nationale de la Recherche
ID : PlasmoPrim
Organisme : Agence Nationale de la Recherche
ID : ANR-11-LABX-0024
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
Références
J. R. Widhalm, D. Rhodes, Hortic. Res. 2016, 3, 16046-16063.
H. Y. Qiu, P. F. Wang, H. Y. Lin, C. Y. Tang, H. L. Zhu, Y. H. Yang, Chem. Biol. Drug Des. 2018, 91, 681-690.
E. A. Hillard, F. C. de Abreu, D. C. Ferreira, G. Jaouen, M. O. Goulart, C. Amatore, Chem. Commun. 2008, 2612-2628.
L. Salmon-Chemin, E. Buisine, V. Yardley, S. Kohler, M. A. Debreu, V. Landry, C. Sergheraert, S. L. Croft, R. L. Krauth-Siegel, E. Davioud-Charvet, J. Med. Chem. 2001, 44, 548-565;
D. Belorgey, D. A. Lanfranchi, E. Davioud-Charvet, Curr. Pharm. Des. 2013, 19, 2512-2528.
M. Elhabiri, P. Sidorov, E. Cesar-Rodo, G. Marcou, D. A. Lanfranchi, E. Davioud-Charvet, D. Horvath, A. Varnek, Chem. Eur. J. 2015, 21, 3415-3424;
P. Sidorov, I. Desta, M. Chesse, D. Horvath, G. Marcou, A. Varnek, E. Davioud-Charvet, M. Elhabiri, ChemMedChem 2016, 11, 1339-1351.
T. Müller, L. Johann, B. Jannack, M. Bruckner, D. A. Lanfranchi, H. Bauer, C. Sanchez, V. Yardley, C. Deregnaucourt, J. Schrevel, M. Lanzer, R. H. Schirmer, E. Davioud-Charvet, J. Am. Chem. Soc. 2011, 133, 11557-11571.
D. A. Lanfranchi, E. Cesar-Rodo, B. Bertrand, H.-H. Huang, L. Day, L. Johann, M. Elhabiri, K. Becker, D. L. Williams, E. Davioud-Charvet, Org. Biomol. Chem. 2012, 10, 6375-6387;
E. Cesar-Rodo, L. Feng, M. Jida, K. Ehrhardt, M. Bielitza, J. Boilevin, M. Lanzer, D. L. Williams, D. A. Lanfranchi, E. Davioud-Charvet, Eur. J. Org. Chem. 2016, 1982-1993;
K. Urgin, M. Jida, K. Ehrhardt, T. Müller, M. Lanzer, L. Maes, M. Elhabiri, E. Davioud-Charvet, Molecules 2017, 22, 161.
P. C. B. Halicki, L. A. Ferreira, K. C. G. De Moura, P. F. Carneiro, K. P. Del Rio, T. D. S. C. Carvalho, M. D. C. F. R. Pinto, P. E. A. da Silva, D. F. Ramos, Front Microbiol. 2018, 9, 673;
S. B. Vafai, E. Mevers, K. W. Higgins, Y. Fomina, J. Zhang, A. Mandinova, D. Newman, S. Y. Shaw, J. Clardy, V. K. Mootha, PLoS One 2016, 11, e0162686;
C. O. Salas, M. Faundez, A. Morello, J. D. Maya, R. A. Tapia, Curr. Med. Chem. 2011, 18, 144-161.
J. Yang, D. Knueppel, B. Cheng, D. Mans, S. F. Martin, Org. Lett. 2015, 17, 114-117;
D. Knueppel, J. Yang, B. Cheng, D. Mans, S. F. Martin, Tetrahedron 2015, 71, 5741-5757.
G. A. Kraus, J. Mengwasser, Molecules 2009, 14, 2857-2861;
L. Johann, D. A. Lanfranchi, E. Davioud-Charvet, M. Elhabiri, Curr Pharm. Des. 2012, 18, 3539-3566;
M. Bielitza, D. Belorgey, K. Ehrhardt, L. Johann, D. A. Lanfranchi, V. Gallo, E. Schwarzer, F. Mohring, E. Jortzik, D. L. Williams, K. Becker, P. Arese, M. Elhabiri, E. Davioud-Charvet, Antioxid. Redox Signaling 2015, 22, 1337-1351.
M. Buccini, M. J. Piggott, Org. Lett. 2014, 16, 2490-2493.
B. S. Joshi, Q. Jiang, T. Rho, S. W. Pelletier, J. Org. Chem. 1994, 59, 8220-8223;
F. M. Hauser, H. Yin, Org. Lett. 2000, 2, 1045-1047.
M. Oelgemöller, C. Schiel, R. Frohlich, J. Mattay, Eur. J. Org. Chem. 2002, 2465-2474;
J. Benites, D. Rios, P. Diaz, J. A. Valderrama, Tetrahedron Lett. 2011, 52, 609-611.
L. Feng, D. A. Lanfranchi, L. Cotos-Munoz, E. Cesar Rodo, K. Ehrhardt, A.-A. Goetz, H. Zimmerman, F. Fenaille, S. Blandin, E. Davioud-Charvet, Org. Biomol. Chem. 2018, 16, 2647-2665.
G. Kranzlein, Aluminium Chloride in der Organischen Chemie, 3rd ed., Verlag Chemie, Berlin, 1939;
C. A. Thomas, Anhydrous Aluminium Chloride in Organic Chemistry, Rainhold, New York, 1961.
S. Paul, P. Nanda, R. Gupta, A. Loupy, Synthesis 2003, 2877-2881.
M. H. Sarvari, H. Sharghi, J. Org. Chem. 2004, 69, 6953-6956.
G. A. Olah, R. Malhorta, S. C. Narang, J. A. Olah, Synthesis 1978, 672-673.
O. Akiko, M. Katsuya, O. Hideaki, Y. Noriyuki, Synth. Commun. 2007, 37, 2701-2715;
I. R. Butler, J. O. Morley, J. Chem. Res. (S) 1980, 10, 358-359.
A. G. Posternak, R. Yu. Garlyauskayte, L. M. Yagupolskii, Tetrahedron Lett. 2009, 50, 446-447.
J. Izumi, T. Mukaiyama, Chem. Lett. 1996, 25, 739-740;
K. Shū, I. Shunsuke, Tetrahedron Lett. 1998, 39, 4697-4700.
F. Effenberger, G. Epple, Angew. Chem. Int. Ed. Engl. 1972, 11, 299-300;
Angew. Chem. 1972, 84, 294-295;
F. Effenberger, G. Epple, Angew. Chem. Int. Ed. Engl. 1972, 11, 300-301;
Angew. Chem. 1972, 84, 295-296;
F. Effenberger, E. Sohn, G. Epple, Chem. Ber. 1983, 116, 1195-1208.
J. J. Li, L. H. Mitchell, R. L. Dow, Bioorg. Med. Chem. Lett. 2010, 20, 306-308;
Z. Wu, G. Wei, G. Lian, B. Yu, J. Org. Chem. 2010, 75, 5725-5728.
H. Sharghi, B. Kaboudin, J. Chem. Res. Synop. 1998, 628-629.
H. Sharghi, M. Hosseini-Sarvari, R. Eskandari, Synthesis 2006, 2047-2052;
M. Hosseini-Sarvari, H. Sharghi, Synthesis 2004, 2165-2168.
S. Grasso, G. De Sarro, A. De Sarro, N. Micale, M. Zappalà, G. Puja, M. Baraldi, C. De Micheli, J. Med. Chem. 2000, 43, 2851-2859;
M. Zappalà, S. Grasso, N. Micale, S. Polimeni, C. De Micheli, Synth. Commun. 2002, 32, 527-533;
M. Zappalà, A. Pellicanò, N. Micale, F. S. Menniti, G. Ferreri, G. De Sarro, S. Grasso, C. De Micheli, Bioorg. Med. Chem. Lett. 2006, 16, 167-170.
A. Zarei, A. R. Hajipour, L. Khazdooz, Tetrahedron Lett. 2008, 49, 6715-6719.
M. C. Wilkinson, Org. Lett. 2011, 13, 2232-2235.
D. Tejedor, L. Cotos, D. Marquez-Arce, M. Odriozola-Gimeno, M. Torrent-Sucarrat, F. P. Cossio, F. Garcia-Tellado, Chem. Eur. J. 2015, 21, 18280-18289.
G. Mlostoń, R. Hamera, H. Heimgartner, Phosphorus Sulfur Silicon Relat. Elem. 2015, 190, 2125-2133.
Z.-Y. Lin, Y.-L. Chen, C.-S. Lee, C.-P. Chuang, Eur. J. Org. Chem. 2010, 3876-3882.
M. C. Pirrung, R. J. Tepper, J. Org. Chem. 1995, 60, 2461-2465.
J. McNulty, P. Das, Tetrahedron 2009, 65, 7794-7800;
D. Van Leusen, A. M. Van Leusen, Org. React. 2001, 57, 417-666;
S. S. Yan, L. Zhu, J. H. Ye, Z. Zhang, H. Huang, H. Zeng, C. J. Li, Y. Lan, D. G. Yu, Chem. Sci. 2018, 9, 4873-4878;
L. R. Cafiero, T. S. Snowden, Org. Lett. 2008, 10, 3853-3856.
J. Cesar, M. Sollner Dolenc, Tetrahedron Lett. 2001, 42, 7099-7102;
T. Tsuchida, A. Kuroda, H. Nagai, M. Yoshida, T. Nakashima, K. Konuki, K. Isshiki, H. Nakamura, T. Takeuchi, J. Antibiot. 2003, 56, 38-41;
M. B. Khaled, R. K. El Mokadem, J. D. Weaver, J. Am. Chem. Soc. 2017, 139, 13092-13101.
W. R. J. D. Galloway, A. Isidro-Llobet, D. R. Spring, Nat. Commun. 2010, 1, 80.
E. J. Bourne, M. Stacey, J. C. Tatlow, J. M. Tedder, J. Chem. Soc. 1951, 718-720;
E. J. Bourne, M. Stacey, J. C. Tatlow, R. Worrall, J. Chem. Soc. 1954, 2006-2012.
D. Plażuk, J. Zakrzewski, Synth. Commun. 2004, 34, 99-107.
D. Plażuk, J. Zakrzewski, M. Salmain, Org. Biomol. Chem. 2011, 9, 408-417.
T. R. Forbus, Jr., J. C. Martin, J. Org. Chem. 1979, 44, 313-314;
T. R. Forbus, Jr., S. L. Taylor, J. C. Martin, J. Org. Chem. 1987, 52, 4156-4159.
D. A. L. Otte, D. E. Borchmann, C. Lin, M. Weck, K. A. Woerpel, Org. Lett. 2014, 16, 1566-1569.
R. T. Pardasani, P. Pardasani, S. Muktawat, R. Ghosh, T. Mukherjee, Heterocycl. Commun. 1998, 4, 77-80.
W. H. Smith, A. J. Bard, J. Am. Chem. Soc. 1975, 97, 5203-5210;
J. Šarlauskas, V. Miliukienė, Ž. Anusevičius, L. Misevičienė, K. Krikštopaitis, A. Nemeikaitė-Čėnienė, I. Vitėnienė, N. Čėnas, Chemija 2009, 20, 109-115;
J. Šarlauskas, A. Nemeikaitė-Čėnienė, L. Misevičienė, K. Krikštopaitis, Ž. Anusevičius, N. Čėnas, Acta Biochim. Pol. 2013, 60, 227-231;
O. Hammerich in Organic Electrochemistry, Revised and Expanded, 5th ed. (Eds.: O. Hammerich, B. Speiser) CRC Press, Boca Raton, 2015, Chapter 30, pp. 1149-1201.
H. A. Seow, P. G. Penketh, R. P. Baumann, A. C. Sartorelli, Methods Enzymol. 2004, 382, 221-233.
N. M. Archer, N. Petersen, M. A. Clark, C. O. Buckee, L. M. Childs, M. T. Duraisingh, Proc. Natl. Acad. Sci. USA 2018, 115, 7350-7355.