New NH-substituted 1,4-naphtho- and 1,4-benzo- quinones: Synthesis, characterization and potential antiproliferative effect against MDA-MB-231 cells

References

• Tandon, V.-K.; Maurya, H.-K.; Verma, M.-K.; Kumar, R.; Shukla, P.-K. On Water’ Assisted Synthesis and Biological Evaluation of Nitrogen and Sulfur Containing Hetero-1,4-Naphthoquinones as Potent Antifungal and Antibacterial Agents. Eur. J. Med. Chem. 2010, 45, 2418–2426. DOI:10.1016/j.ejmech.2010.02.023.
   PubMed Web of Science ®Google Scholar
• Delarmelina, M.; Daltoe, R.-D.; Cerri, M.-F. Madeira; ,. J. Braz. Chem. Soc. 2015, 26, 1804–1816. K.-P.; Rangel, L.-B.-A.; Junior, V.-L.; Romao, W.; Taranto, A.-G.; Greco, S.-J. Synthesis, Antitumor Activity and Docking of 2,3-(Substituted)-1,4-Naphthoquinone Derivatives Containing Nitrogen, Oxygen and Sulfur. http://dx.doi.org/10.5935/0103-5053.20150157
   Web of Science ®Google Scholar
• Silva, M.-G.; Camara, C.-A.; Silva, T.-M.-S.; Feitosa, A.-C.-S.; Meira, A.-S.; Pessoa, C. Synthesis of 2,3-Diyne-1,4-Naphthoquinone Derivatives and Evaluation of Cytotoxic Activity against Tumor Cell Lines. J. Braz. Chem. Soc. 2013, 24, 1420–1426. http://dx.doi.org/10.5935/0103-5053.20130180
   Web of Science ®Google Scholar
• Perez-Sacau, E.; Diaz-Penate, R.-G.; Estevez-Braun, A.; Ravelo, A.-G.; Garcia-Castellano, J.-M.; Pardo, L.; Campillo, M. Synthesis and Pharmacophore Modeling of Naphthoquinone Derivatives with Cytotoxic Activity in Human Promyelocytic Leukemia HL-60 Cell Line. J. Med. Chem. 2007, 50, 696–706. DOI: 10.1021/jm060849b
   PubMed Web of Science ®Google Scholar
• Valderrama, J. A.; Leiva, H.; Rodríguez, J. A.; Theoduloz, C.; Schmeda-Hirshmann, G. Studies on Quinones. Part 43: Synthesis and Cytotoxic Evaluation of Polyoxyethylene-Containing 1,4-Naphthoquinones. Bioorg. Med. Chem. 2008, 16, 3687–3693. DOI: 10.1016/j.bmc.2008.02.018
   PubMed Web of Science ®Google Scholar
• Barbosa, T.-P.; Camara, C.-A.; Silva, T.-M.-S.; Martins, R.-M.; Pinto, A.-C.; Vargas, M.-D. New 1,2,3,4-Tetrahydro-1-Aza-Anthraquinones and 2-Aminoalkyl Compounds from Norlapachol with Molluscicidal Activity. Bioorg. Med. Chem. 2005, 13, 6464–6469. DOI: 10.1016/j.bmc.2005.06.068
   PubMed Web of Science ®Google Scholar
• Silva, T.-M.-S.; Camara, C.-A.; Barbosa, T.-P.; Soares, A.-Z.; da Cunha, L.-C.; Pinto, A.-C.; Vargas, M.-D. Molluscicidal Activity of Synthetic Lapachol Amino and Hydrogenated Derivatives. Bioorg. Med. Chem. 2005, 13, 193–196. DOI: 10.1016/j.bmc.2004.09.043
   PubMed Web of Science ®Google Scholar
• Kumagai, Y.; Shinkai, Y.; Miura, T.; Cho, A.-K. The Chemical Biology of Naphthoquinones and Its Environmental Implications. Annu. Rev. Pharmacol. Toxicol. 2012, 52, 221–247. DOI: 10.1146/annurev-pharmtox-010611-134517
   PubMed Web of Science ®Google Scholar
• Ryu, C.-K.; Choi, K.-U.; Shim, J.-Y.; You, H.-J.; Choi, I. H.; Chae, M.-J. Synthesis and Antifungal Activity of 6-Arylthio-/6-Arylamino-4,7-Dioxobenzothiazoles. Bioorg. Med. Chem. 2003, 11, 4003–4008. DOI:10.1016/S0968-0896(03)00390-0
   PubMed Web of Science ®Google Scholar
• Tran, T.; Saheba, E.; Arcerio, A.-V.; Chavez, V.; Li, Q-y.; Martinez, L.-E.; Primm, T.-P. Quinones as Antimycobacterial Agents. Bioorg. Med. Chem. 2004, 12, 4809–4813. DOI:10.1016/j.bmc.2004.07.015
   PubMed Web of Science ®Google Scholar
• Lien, J.-C.; Huang, L.-J.; Wang, J.-P.; Teng, C.-M.; Lee, K.-H.; Kuo, S.-C. Synthesis and Antiplatelet, Antiinflammatory, and Antiallergic Activities of 2-Substituted 3-Chloro-l,4-Naphthoquinone Derivatives. Bioorg. Med. Chem. 1997, 5, 2111–2120.
   PubMed Web of Science ®Google Scholar
• Tjepkema, J.-J. Manufacture of Organomercapto Substituted Quinones. US Patent 2691661, 1954.
   Google Scholar
• Neves-Pinto, C.; Malta, V.-R.-S.; F.-R. Pinto, MdC.; Santos, R.-H.-A.; de Castro, S.-L.; Pinto, A.-V. A Trypanocidal Phenazine Derived from β-Lapachone. J. Med. Chem. 2002, 45, 2112–2115. DOI: 10.1021/jm010377v
   PubMed Web of Science ®Google Scholar
• Szymczak, A. M.; Podsiadły, R.; Podemska, K.; Sokołowska, J. Dyes Derived from 1,4-Naphthoquinone as Initiators for Radical and Cationic Photopolymerisation. Color. Technol. 2012, 128, 378–386. DOI: 10.1111/j.1478-4408.2012.00391.x
   Web of Science ®Google Scholar
• Fornier, M.; Fumoleau, P. The Paradox of Triple Negative Breast Cancer: Novel Approaches to Treatment. Breast J. 2012, 18, 41–51. DOI: 10.1111/j.1524-4741.2011.01175.x.
   PubMed Web of Science ®Google Scholar
• The Cancer Genome Atlas Network Comprehensive Molecular Portraits of Human Breast Tumours. Nature 2012, 490, 61–70. https://doi.org/10.1038/nature11412
   PubMed Web of Science ®Google Scholar
• Mahmood, T. Aspects of the Chemistry of 1,4-Naphthoquinones, University of Bradford, Bradford, West Yorkshire, UK, 2012.
   Google Scholar
• Singh, V.-K.; Verma, S.-K.; Kadu, R.; Mobin, S.-M. Identification of Unusual C–Cl…л Contacts in 2-(Alkylamino)-3-Chloro-1,4-Naphthoquinones: effect of N-Substituents on Crystal Packing, Fluorescence, Redox and anti-Microbial Properties. RSC Adv. 2015, 5, 43669–43686. DOI: 10.1039/C5RA02295A
   Web of Science ®Google Scholar
• Salunke-Gawali, S.; Pawar, O.; Nikalje, M.; Patil, R.; Weyhermüller, T.; Puranik, V.-G.; Konkimalla, V.-B. Synthesis, Characterization and Molecular Structures of Homologated Analogs of 2-Bromo-3-(n-Alkylamino)-1,4-Napthoquinone. J. Mol. Struct. 2014, 1056–1057, 97–1057. 97-103. http://dx.doi.org/10.1016/j.molstruc.2013.10.016
   Web of Science ®Google Scholar
• Santos, M.-M.-M.; Faria, N.; Iley, J.; Coles, S.-J.; Hursthouse, M.-B.; Martins, M.-L.; Moreira, R. Reaction of Naphthoquinones with Substituted Nitromethanes. Facile Synthesis and Antifungal Activity of Naphtho[2,3-d]Isoxazole-4,9-Diones. Bioorg. Med. Chem. Lett. 2010, 20, 193–195. https://doi.org/10.1016/j.bmcl.2009.10.137
   PubMed Web of Science ®Google Scholar
• Tapia, R.-A.; Cantuarias, L.; Cuellar, M.; Villena, J. Microwave-Assisted Reaction of 2,3-Dichloronaphthoquinone with Aminopyridines. J. Braz. Chem. Soc. 2009, 20, 999–1002. http://dx.doi.org/10.1590/S0103-50532009000500027
   Web of Science ®Google Scholar
• Mandal, A.; Mondal, S.-K.; Jana, A.; Manna, S.-K.; Ali, S. A.; Samanta, S. Pd‐Catalyzed C‐H Arylation: A General Route for the Synthesis of Benzo[b]Carbazolenaphthoquinones. J. Heterocyclic Chem. 2017, 54, 2529–2535. https://doi.org/10.1002/jhet.2832
   Web of Science ®Google Scholar
• Chung-Kyu, R.; Dong-Hyun, K. The Synthesis and Antimicrobial Activities of Some 1,4-Naphthoquinones (II). Arch. Pharm. Res. 1992, 15, 263–268.
   Google Scholar
• Bowen, R.-D.; Mahmood, T.; Maitland, D.-J.; Mercer, K.-E.; Gallagher, R.-T. Evidence of Structure-Selective Fragmentations in the Tandem Mass Spectra of Protonated Hydroxyalkylamino-1,4-Naphthoquinones Formed by Electrospray Ionisation. Eur. J. Mass Spectrom. (Chichester). 2009, 15, 617–626. https://doi.org/10.1255/ejms.1023
   PubMed Web of Science ®Google Scholar
• Nguyen Van, T.; De Kimpe, N. Synthesis of 6H-Naphtho[2,3-c]Chromene-7,12-Diones via Palladium-Catalyzed Intramolecular Cyclization of 2-Bromo-3-Aryloxymethyl-1,4-Naphthoquinones. Tetrahedron 2003, 59, 5941–5946. https://doi.org/10.1016/S0040-4020(03)00874-3
   Web of Science ®Google Scholar
• Kutyrev, A.-A. Nucleophilic Reactions of Quinones. Tetrahedron 1991, 47, 8043–8065.
   Web of Science ®Google Scholar
• Yang, J.; Cohen Stuart, M.-A.; Kamperman, M. Jack of All Trades: versatile Catechol Crosslinking Mechanisms. Chem. Soc. Rev. 2014, 43, 8271–8298. DOI: 10.1039/c4cs00185k
   PubMed Web of Science ®Google Scholar
• Barbosa, L.-C.-A.; Pereira, U.-A.; Maltha, C.-R.-A.; Teixeira, R.-R.; Valente, V.-M.-M.; Ferreira, J.-R.-O.; Costa-Lotufo, L.-V.; Moraes, M.-O.; Pessoa, C. Synthesis and Biological Evaluation of 2,5-Bis(Alkylamino)-1,4-Benzoquinones. Molecules 2010, 15, 5629–5643. DOI:10.3390/molecules15085629
   PubMed Web of Science ®Google Scholar
• Bayen, S.; Barooah, N.; Sarma, R.-J.; Sen, T.-K.; Karmakar, A.; Baruah, J.-B. Synthesis, Structure and Electrochemical Properties of 2,5-Bis(Alkyl/Arylamino)1,4-Benzoquinones and 2-Arylamino-1,4-Naphthoquinones. Dyes. Pigm. 2007, 75, 770–775. DOI:10.1016/j.dyepig.2006.07.033
   Web of Science ®Google Scholar
• Nain-Perez, A.; Barbosa, L.-C.-A.; Picanco, M.-C.; Giberti, S.; Forlani, G. Amino-Substituted Para-Benzoquinones as Potential Herbicides. Chem. Biodiv. 2016, 13, 1008–1017. DOI:10.1002/cbdv.201500340
   PubMed Web of Science ®Google Scholar
• MacGregor, K.-A.; Abdel-Hamid, M.-K.; Odell, L. R.; Chau, N.; Whiting, A.; Robinson, P.-J.; McCluskey, A. Development of Quinone Analogues as Dynamin GTPase Inhibitors. Eur. J. Med. Chem. 2014, 85, 191–206. https://doi.org/10.1016/j.ejmech.2014.06.070
   PubMed Web of Science ®Google Scholar
• Kolesnikov, V.-T.; Romashkin, M.-P. Vestnik L'vovskogo Politekhnicheskogo Instituta. Some Derivatives of 1,4-Benzoquinone 1975, 96, 26–31. ISSN:0460-0436
   Google Scholar
• Kathawate, L.; Sproules, S.; Pawar, O.; Markad, G.; Haram, S.; Puranik, V.; Salunke-Gawali, S. Synthesis and Molecular Structure of a Zinc Complex of the Vitamin K3 Analogue Phthiocol. J. Mol. Struct. 2013, 1048, 223–229. https://doi.org/10.1016/j.molstruc.2013.05.057
   Web of Science ®Google Scholar
• Win, T.; Bittner, S. Novel 2-Amino-3-(2,4-Dinitrophenylamino) Derivatives of 1,4-Naphthoquinone. Tetrahedron Lett. 2005, 46, 3229–3231. https://doi.org/10.1016/j.tetlet.2005.03.041
   Web of Science ®Google Scholar
• Silver, R.-F.; Holmes, H.-L. Synthesis of Some 1,4-Naphthoquinones and Reactions Relating to Their Use in the Study of Bacterial Growth Inhibition. Can. J. Chem. 1968, 46, 1859–1864.
   Web of Science ®Google Scholar
• Chu, K.-Y.; Griffiths, J. Naphthoquinone Colouring Matters. Part 1. Synthesis and Electronic Absorption Spectra of 1,4-Naphthoquinone Derivatives with Electron-Donating Groups in the Quinonoid Ring. J. Chem. Soc, Perkin Trans. 1 1978, 9, 1083–1087. DOI:10.1039/P19780001083
   Google Scholar
• Perpete, E.-A.; Lambert, C.; Wathelet, V.; Preat, J.; Jacquemin, D. Ab Initio Studies of the Λmax of Naphthoquinones Dyes. Spectrochim. Acta Part A 2007, 68, 1326–1333. DOI:10.1016/j.saa.2007.02.012
   PubMed Web of Science ®Google Scholar
• Záliš, S.; Fiedler, J.; Pospı́šil, L.; Fanelli, N.; Lanza, C.; Lampugnani, L. Electron Transfer in Donor–Acceptor Molecules of Substituted Naphtoquinones: Spectral and Redox Properties of Internal Charge Transfer Complexes. Microchem. J. 1996, 54, 478–486. https://doi.org/10.1006/mchj.1996.0125
   PubMed Web of Science ®Google Scholar
• Nithianandam, V.-S.; Erhan, S. Quinone-Amine Polymers: 18 a Novel Method for the Synthesis of Poly(Alkylaminoquinone)s. Polymer. 1998, 39, 4095–4098. https://doi.org/10.1016/S0032-3861(97)10301-9
   Web of Science ®Google Scholar