Abstract
Herein, we report design, synthesis and spectral characterization of novel 4-ferrocenyl-8-(phenylthio)-1,2,3,4-tetrahydroquinoline. Desired synthesis was achieved in three reaction steps, with a good overall yield (67%). First step included aza-Michael addition of 2-(phenylthio)aniline to 1-ferrocenylpropenone, subsequently, the obtained ketone was smoothly reduced to the corresponding 1,3-amino alcohol. The final step was an intramolecular cyclization prompted by acetic acid, proceeding via corresponding α-ferrocenyl carbocation. The synthesized compounds have been isolated pure, and their structure have been undoubtedly confirmed by standard spectral techniques (1H NMR, 13C NMR, IR and elemental analyses).
Keywords
Array
Array
Array
Array
References
Biot, C., Castro, W., Botte, C. Y., & Navarro, M. 2012. The therapeutic potential of metal-based antimalarial agents: Implications for the mechanism of action. Dalton Transactions, 41, pp. 6335-6349. doi.10.1039/C2DT12247B
Bleiholder, C., Rominger, F., & Gleiter, R. 2009. α-Metallocenylmethylium Ions and Their Isoelectronic Congeners: A Comparison Based on DFT Calculations. Organometallics, 28, pp. 1014-1017. doi. 10.1021/om800573u
Dai, Z., Ni, J., Huang, X., Lu, G., & Bao, J. 2007. Direct electrochemistry of glucose oxidase immobilized on a hexagonal mesoporous silica-MCM-41 matrix. Bioelectrochemistry, 70, pp 250-256. doi.org/10.1016/j.bioelechem.2006.09.009
Damljanović, I., Stevanović, D., Pejović, A., Vukićević, M., Novaković, S. B., Bogdanović, G. A., Mihajilov-Krstev, M. T., Radulović, N. & Vukićević, R. D. 2011. Antibacterial 3-(arylamino)-1-ferrocenylpropan-1-ones: Synthesis, spectral, electrochemical and structural characterization. Journal of Organometallic Chemistry, 696, pp. 3703-3713. doi.org/10.1016/j.jorganchem.2011.08.016
Eicher, T., Hauptmann, S., & Speicher, A. 2003. The Chemistry of Heterocycles: Structure, Reactions, Syntheses, and Applications. Wiiey-VCH Veriag. 2nd ed., doi.10.1002/352760183X
Gambino, D., & Otero, L. 2012. Perspectives on what ruthenium-based compounds could offer in the development of potential antiparasitic drugs. Inorganica Chimica Acta, 393, pp. 103–114. doi.10.1016/j.ica.2012.05.028
Houlton, A., Roberts, R. M. G., & Silver, J. 1991. Studies on the anti-tumour activity of some iron sandwich compounds. Journal of Organometallic Chemistry, 418, pp. 107-112. doi.org/10.1016/0022-328X(91)86350-Y
Jaouen, G. 2006. Bioorganometallics: Biomolecules, Labeling, Medicine. Weinheim, FRG: John Wiley. doi:10.1002/3527607692
Kelland, L. 2007. The resurgence of platinum-based cancer chemotherapy. Nature Reviews Cancer, 7(8), pp. 573-584. doi:10.1038/nrc2167
Kowalski, K. 2018. Recent developments in the chemistry of ferrocenyl secondary natural product conjugates. Coordination Chemistry Reviews, 366, pp. 91-108. doi:10.1016/j.ccr.2018.04.008
Köpf‐Maier, P., Köpf, H., & Neuse, E. W. 1984. Ferrocenium Salts-The First Antineoplastic Iron Compounds. Angewandte Chemie International Edition, in English, 23, pp. 456-457. doi.org/10.1002/anie.198404561
Madrid, P. B., Liou, A. P., Derisi, J. L., & Guy, R. K. 2006. Incorporation of an Intramolecular Hydrogen-Bonding Motif in the Side Chain of 4-Aminoquinolines Enhances Activity against Drug-Resistant P. Falciparum. Journal of Medicinal Chemistry, 49, pp. 4535-4543. doi.10.1021/jm0600951
Malisa, A. L., Pearce, R. J., Mutayoba, B. M., Abdullah, S., Mshinda, H., Kachur, P. S., Bloland, P. & Roper, C. 2011. The evolution of pyrimethamine resistant dhfr in Plasmodium falciparum of south-eastern Tanzania: comparing selection under SP alone vs SP+artesunate combination. Malaria Journal, 10(317), pages 13. doi.10.1186/1475-2875-10-317
Minić, A., Bugarinović, J., Ilić-Komatina, D., Bogdanović, G. A., Damljanović, I., & Stevanović, D. 2018. Synthesis of novel ferrocene-containing 1, 3-thiazinan-2-imines: One-pot reaction promoted by ultrasound irradiation. Tetrahedron Letters, 59, pp. 3499-3502. doi. 10.1016/j.tetlet.2018.08.029
Minić, A., Stevanović, D., Damljanović, I., Pejović, A., Vukićević, M., Bogdanović, G. A., Radulović, N. & Vukićević, R. D. 2015. Synthesis of ferrocene-containing six-membered cyclic ureas via α-ferrocenyl carbocations. RSC Advances, 5, pp. 24915-24919. doi. 10.1039/C5RA01383F
Minić, A., Stevanović, D., Vukićević, M., Bogdanović, G. A., D'hooghe, M., Radulović, N., & Vukićević, R. D. 2017. Synthesis of novel 4-ferrocenyl-1, 2, 3, 4-tetrahydroquinolines and 4-ferrocenylquinolines via α-ferrocenyl carbenium ions as key intermediates. Tetrahedron, 73, pp 6268-6274. doi. 10.1016/j.tet.2017.09.014
N'da, D., & Smith, P. 2014. Synthesis, in vitro antiplasmodial and antiproliferative activities of a series of quinoline-ferrocene hybrids. Medicinal Chemistry Research, 23, pp. 1214-1224. doi.org/10.1007/s00044-013-0748-4
Pejović, A., Stevanović, D., Damljanović, I., Vukićević, M., Novaković, S. B., Bogdanović, G. A., Mihajilov-Krstev, M. T., Radulović, N. & Vukićević, R. D. 2012. Ultrasound‐assisted synthesis of 3‐(arylamino)‐1‐ferrocenylpropan‐1‐ones. Helvetica Chimica Acta, 95, pp. 1425-1441. doi.org/10.1002/hlca.201200009
Pejović, A., Danneels, B., Desmet, T., Cham, B. T., Nguyen, T., Radulović, N. S., Vukićević, R. D., & D'hooghe, M. 2015. Synthesis and Antimicrobial/Cytotoxic Assessment of Ferrocenyl Oxazinanes, Oxazinan-2-ones, and Tetrahydropyrimidin-2-ones. Synlett, p. 1195-1200. doi. /s-0034-1380348
Salas, P. F., Herrmann, C., & Orvig, C. 2013. Metalloantimalarials. Chemical Reviews, 113, pp. 3450-3492. doi.10.1021/cr3001252
Supan, C., Mombo-Ngoma, G., Dal-Bianco, M. P., Salazar, C. L. O., Issifou, S., Mazuir, F., Filali-Ansary, A., Biot, C., Ter-Minassian, D., Ramharter, M., Kremsner, P. G. & Lell, B. 2012. Pharmacokinetics of Ferroquine, a Novel 4-Aminoquinoline. In Asymptomatic Carriers of Plasmodium falciparum Infections. Antimicrobial Agents and Chemotherapy. 56, pp. 3165–3173. doi. 10.1128/AAC.05359-11
Sridharan, V., Suryavanshi, P. A., & Menéndez, J. C. 2011. Advances in the Chemistry of Tetrahydroquinolines. Chemical Reviews, 111(11) p.p. 7157-7259. doi.10.1021/cr100307m
Taylor, A. P., Robinson, R. P., Fobian, Y. M., Blakemore, D.C., Jones, L. H., & Fadeyi, O. 2016. Modern advances in heterocyclic chemistry in drug discovery. Organic and Biomolecular Chemistry, 14, pp. 6611-6637. doi.10.1039/C6OB00936K
Togni, A. 1996. Planar-Chiral Ferrocenes: Synthetic Methods and Applications. Angewandte Chemie International Edition in English, 35(1314), pp. 1475-1477. doi:10.1002/anie.199614751
Authors retain copyright and grant the journal right of first publication with the work simultaneously licensed under a Creative Commons Attribution License that allows others to share the work with an acknowledgement of the work's authorship and initial publication in this journal.