Novel amino- and thio(substituted)-1,4-naphthoquinone (NQ) compounds: Synthesis and characterization

References

• Berkheij, M.; Sluis, L.; Sewing, C.; Boer, D. J.; Terpstra, J. W.; Hiemstra, H.; Iwema Bakker, W. I.; Hoogenband, A.; Maarseveen, J. H. Synthesis of 2-Substituted Piperazines via Direct α-Lithiation. Tetrahedron Lett 2005, 46, 2369–2371. DOI: 10.1016/j.tetlet.2005.02.085.
   Web of Science ®Google Scholar
• Upadhayaya, R. S.; Sinha, N.; Jain, S.; Kishore, N.; Chandra, R.; Arora, S. K. Optically Active Antifungal Azoles: synthesis and Antifungal Activityof (2R,3S)-2-(2,4-Difluorophenyl)-3-(5-{2-[4-Aryl-Piperazin-1-yl]-Ethyl}-Tetrazol-2-yl/1-yl)-1-[1,2,4]-Triazol-1-yl-Butan-2-ol. Bioorg. Med. Chem 2004, 12, 2225–2238. DOI: 10.1016/j.bmc.2004.02.014.
   PubMed Web of Science ®Google Scholar
• Chaudhary, P.; Kumar, R.; Verma, A. K.; Singh, D.; Yadav, V.; Chhillar, A. K.; Sharma, G. L.; Chandra, R. Synthesis and Antimicrobial Activity of N-Alkyl and N-Aryl Piperazine Derivatives. Bioorg. Med. Chem 2006, 14, 1819–1826. DOI: 10.1016/j.bmc.2005.10.032.
   PubMed Web of Science ®Google Scholar
• Brun, M. P.; Braud, E.; Angotti, D.; Mondesert, O.; Quaranta, M.; Montes, M.; Miteva, M.; Gresh, N.; Ducommun, B.; Garbay, C. Design, Synthesis, and Biological Evaluation of Novel Naphthoquinone Derivatives with CDC25 Phosphatase Inhibitory Activity. Bioorg. Med. Chem 2005, 13, 4871–4879. DOI: 10.1016/j.bmc.2005.05.005.
   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. 4408.2012.00391.x. DOI: 10.1111/j.1478-.
   Web of Science ®Google Scholar
• Koroteev, N. I.; Magnıtskii, S. A.; Shubin, V. V.; Sokolyuk, N. T. Photochemical and Spectroscopic Properties of Naphthacenequinones Ascandidates for 3D Optical Data Storage. Jpn. J. Appl. Phys. 1997, 36, 424–425. DOI: 10.1143/JJAP.36.424.
   Web of Science ®Google Scholar
• Ohkura, K.; Takeshima, M.; Omokawa, S.; Hasegawa, Y.; Kobayashi, T. Quinone, Compound, electrophotographic photoconductor and electrophotographic apparatus. US Patent 2006/0204874, Sep. 14, 2006.
   Google Scholar
• Won, J. H.; Latifatu, M.; Jang, M.; Lee, H. S.; Kim, B. C.; Hamenu, L.; Park, J. H.; Kim, K. M.; Ko, J. M. Supercapacitive Properties of Composite Electrode Consisting of Activated Carbon and a Quinone-Containing Conducting Additive. Synth. Met 2015, 203, 31–36. DOI: 10.1016/j.synthmet.2015.02.010.
   Web of Science ®Google Scholar
• Hamenu, L.; Madzvamuse, A.; Mohammed, L.; Hu, M.; Park, J.; Ryou, M. H.; Lee, Y. M.; Ko, J. M. Highly Stable 2,3,5,6-Tetrachloro-1,4-Benzoquinone Electrodes for Supercapacitors. Synth. Met 2017, 231, 25–33. DOI: 10.1016/j.synthmet.2017.06.006.
   Web of Science ®Google Scholar
• Singh, D.; Kushwaha, A.; Banerjee, A.; Prasad, R. L. Synthesis and Characterization of Multifunctional Coordination Polymer of the Type [CuxNi1-x(Dedb) · 2 H2O]n. Solid State Sci 2015, 45, 35–45. DOI: 10.1016/j.solidstatesciences.2015.04.004.
   Web of Science ®Google Scholar
• Gafner, S.; Wolfender, J. L.; Nianga, M.; Stoeckli-Evans, H.; Hostettmann, K. Antifungal and Antibacterial Naphthoquinones from Newbouldia Laevis Roots. Phytochemistry 1996, 42, 1315–1320. DOI: 10.1016/0031-9422(96)00135-5.
   PubMed Web of Science ®Google Scholar
• Yıldırım, H.; Bayrak, N.; Yıldız, M.; Kara, E. M.; Celik, B. O.; Tuyun, A. F. Thiolated Plastoquinone Analogs: Synthesis, Characterization, and Antimicrobial Evaluation. J. Mol. Struct 2019, 1195, 681–688. DOI: 10.1016/j.molstruc.2019.05.076.
   Web of Science ®Google Scholar
• Huang, L.-J.; Chang, F.-C.; Lee, K.-H.; Wang, J.-P.; Teng, C.-M.; Kuo, S.-C. Synthesis and Antiplatelet, Antiinflammatory, and Antiallergic Activities of Substituted 3-Chloro-5,8-Dimethoxy-1,4-Naphthoquinone and Related Compounds. Bioorg. Med. Chem 1998, 6, 6, 2261–2269. DOI: 10.1016/S0968-0896(98)80006-0.
   PubMed Web of Science ®Google Scholar
• Ma, W.; Zhou, H.; Ying, Y. L.; Li, D. W.; Chen, G. R.; Long, Y. T.; Chen, H. Y. In Situ Spectroeletrochemistry and Cytotoxic Activities of Natural Ubiquinone Analogues. Tetrahedron 2011, 67, 5990–6000. DOI: 10.1016/j.tet.2011.06.026.
   Web of Science ®Google Scholar
• Ganesh, K.; Balraj, C.; Satheshkumar, A.; Elango, K. P. Spectroscopic Studies on the Formation of Molecular Complexes of Sulfamethoxazole with Novel 2,3,5-Trichloro-6-Alkoxy-1,4-Benzoquinones. J. Mol. Struct 2013, 1033, 312–320. DOI: 10.1016/j.molstruc.2012.09.062.
   Web of Science ®Google Scholar
• Delarmelina, M.; Daltoe, R. D.; Cerri, M. F.; Madeira, 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. J. Brazil Chem. Soc 2015, 26, 1804–1816. DOI: 10.5935/0103-5053.20150157.
   Web of Science ®Google Scholar
• Karakaş, D.; Akar, R. O.; Gökmen, Z.; Deniz, N. G.; Ulukaya, E. A Novel 1,4-Naphtoquinone-Derived Compound Induces Mitochondria-Mediated Apoptotic Cell Death in Breast Cancer Cells. Turk. J. Biol. 2019, 43, 256–263. DOI: 10.3906/biy-1901-19.
   PubMed Web of Science ®Google Scholar
• Song, G. Y.; Kim, Y.; You, Y. J.; Cho, H.; Kim, S. H.; Sok, D. E.; Ahn, B. Z. Naphthazarin Derivatives (VI): Synthesis, Inhibitory Effect on DNA Topoisomerase-I and Antiproliferative Activity of 2- or 6-(1-Oxyiminoalkyl)-5,8-Dimethoxy-1,4-Naphthoquinones. Arch. Pharm. Pharm. Med. Chem. 2000, 333, 87–92. DOI: 10.1002/(SICI)1521-4184(20004)333:4 < 87::AID-ARDP87 > 3.0.CO:2-1.
   PubMed Web of Science ®Google Scholar
• Deniz, N.; Ibis, C.; Gokmen, Z.; Stasevych, M.; Novikov, V.; Komarovska-Porokhnyavets, O.; Ozyurek, M.; Guclu, K.; Karakas, D.; Ulukaya, E. Design, Synthesis, Biological Evaluation, and Antioxidant and Cytotoxic Activity of Heteroatom-Substituted 1,4-Naphtho- and Benzoquinones. Chem. Pharm. Bull. 2015, 63, 1029–1039. [Mismatch] DOI: 10.1155/2019/1658417.
   PubMed Web of Science ®Google Scholar
• Gokmen, Z.; Onan M. E.; Deniz N. G.; Karakas D.; Ulukaya E. Synthesis and Investigation of Cytotoxicity of New N- and S,S-Substituted-1,4-Naphthoquinone (NQ) Derivatives on Selected Cancer Lines. Synth. Commun 2019, 49, 1–3016. DOI: 10.1080/00397911.2019.1655057.
   Web of Science ®Google Scholar
• Kacmaz, A.; Deniz, N. G.; Aydinli, S. G.; Sayil, C.; Onay-Ucar, E.; Mertoglu, E.; Arda, N. Synthesis and Antiproliferative Evaluation of Some 1,4-Naphthoquinone Derivatives against Human Cervical Cancer Cells. Open Chem 2019, 17, 337–345. DOI: 10.1515/chem-2019-0030.
   Web of Science ®Google Scholar