Highlights on the chemistry of 2-amino-3-cyano-quinoxaline 1, 4-dioxides and their derivatives

References

• Satsumabayashi, S.; Irioka, S.; Kudo, H.; Tsujimoto, K.; Motoki, S. BCSJ. 1972, 45, 913–915. DOI: 10.1246/bcsj.45.913.
   Google Scholar
• Vanajatha, G.; Reddy, V. P. Syn. Commun. 2016, 46, 1953–1961. DOI: 10.1080/00397911.2016.1242746.
   Web of Science ®Google Scholar
• (a) Varala, R.; Enugala, R.; Adapa, S. R. Synthesis. 2006, 3825.
   Web of Science ®Google Scholar
  (b) Cheng, C. C.; Yan, S. J. Org. React. 1982, 28, 37.
   Web of Science ®Google Scholar
  (c) Madrid, P. B.; Sherrill, J.; Liou, A. P.; Weisman, J. L.; DeRisi, J. L.; Guy, R. K. Bioorg. Med. Chem. Lett. 2005, 15, 1015–1018. DOI: 10.1016/j.bmcl.2004.12.037.
   PubMed Web of Science ®Google Scholar
• Abd El-Wahab, A. H. F. Acta. Pharm. 2002, 54, 269.
   Google Scholar
• (a) Rosowsky, A.; Chen, H. J. J. Org. Chem. 2001, 66, 7522–7526. DOI: 10.1021/jo010536i.
   PubMed Web of Science ®Google Scholar
  (b) Mohareb, R. M.; Al-Omran, F. A.; Ho, J. Z. Monatsh. Chem. 2002, 133, 1443–1452. DOI: 10.1007/s00706-002-0494-7.
   Web of Science ®Google Scholar
  (c) Wiklund, P.; Bergman, J. Org. Biomol. Chem. 2003, 1, 467.
   Google Scholar
• (a) Roth, G. A.; Tai, J. J. J. Heterocycl. Chem. 1996, 33, 2051–2053. . DOI: 10.1002/jhet.5570330680.
   Web of Science ®Google Scholar
  (b) Zhang, P.; Fensome, A.; Terefenko, E. A.; Zhi, L.; Jones, T. K.; Marschke, K. B.; Tegley, C. M. PCT Int. Appl. 2000, WO0066560.
   Google Scholar
• (a) Mizuno, T.; Okamoto, N.; Ito, T.; Miyata, T. Heteroatom Chem. 2000, 11, 428–433. DOI: 10.1002/1098-1071(2000)11:6<428::AID-HC12>3.0.CO;2-Z.
   Web of Science ®Google Scholar
  (b) Mizuno, T. Kagaku Kogyo. 2002, 76, 431.
   Google Scholar
  (c) Yoshida, T. Jpn. Patent. 2004, JP200491403.
   Google Scholar
  (d) Mizuno, T.; Iwai, T.; Ishino, Y. Tetrahedron Lett. 2004, 45, 7073–7075. DOI: 10.1016/j.tetlet.2004.07.152.
   Web of Science ®Google Scholar
  (e) Nourry, A.; Legoupy, S.; Huet, F. Tetrahedron Lett. 2007, 48, 6014–6018. DOI: 10.1016/j.tetlet.2007.06.100.
   Web of Science ®Google Scholar
• Kotovskaya, S. K.; Charushin, V. N.; Perova, N. M.; Kodess, M. I.; Chupakhin, O. Synth. Commun. 2004, 34, 2531–2537. DOI: 10.1081/SCC-200025595.
   Web of Science ®Google Scholar
• Monge, A.; Palop, J. A.; Urbasos, I.; Fernandez-Alvarez, E. J. Heterocycl. Chem. 2009, 26, 1623–1626. DOI: 10.1002/jhet.5570260621.
   Google Scholar
• Urquiola, C.; Vieites, M.; Aguirre, G.; Marın, A.; Solano, B.; Arrambide, G.; Noblia, P.; Lavaggi, M. L.; Torre, M. H.; Gonzalez, M.; et al. Bioorg. Med. Chem. 2006, 14, 5503–5509. DOI: 10.1016/j.bmc.2006.04.041.
   PubMed Web of Science ®Google Scholar
• Torre, M. H.; Gambino, D.; Araujo, J.; Cerecetto, H.; GonzáLez, M.; Lavaggi, M. L.; Azqueta, A.; LóPez de Cerain, A.; Monge Vega, A.; Abram, U.; Costa-Filho, A. J. Eur. J. Med. Chem. 2005, 40, 473–480. DOI: 10.1016/j.ejmech.2004.11.012.
   PubMed Web of Science ®Google Scholar
• Amin, K. M.; Ismail, M. M. F.; Noaman, E.; Soliman, D. H.; Ammar, Y. A. Bioorg. Med. Chem. 2006, 14, 6917–6923. DOI: 10.1016/j.bmc.2006.06.038.
   PubMed Web of Science ®Google Scholar
• Monge, A.; Palop, J. A.; Lopez de Cerain, A.; Senador, V.; Martinez, F. J.; Sainz, Y.; Narro, S.; Garcia, E.; Carlos de Miguel, Gonzalez, M.; Hamilton, E.; et al. J. Med. Chem. 1995, 38, 1786–1792. DOI: 10.1021/jm00010a023.
   PubMed Web of Science ®Google Scholar
• Chowdhury, G.; Kotandeniya, D.; Daniels, J. S.; Barnes, C. L.; Gates, K. S. Chem. Res. Toxicol. 2004, 17, 1399–1405. DOI: 10.1021/tx049836w..
   PubMed Web of Science ®Google Scholar
• Fuchs, T.; Gates, K. S.; Hwang, J. T.; Greenberg, M. M. Chem. Res. Toxicol. 1999, 12, 1190–1194. DOI: 10.1021/tx990149s.
   PubMed Web of Science ®Google Scholar
• Barea, C.; Pabón, A.; Galiano, S.; Pérez-Silanes, S.; Gonzalez, G.; Deyssard, C.; Monge, A.; Deharo, E.; Aldana, I. Molecules. 2012, 17, 9451–9461. DOI: 10.3390/molecules17089451.
   PubMed Web of Science ®Google Scholar
• Wally, M. A.; Ibrahim, I. T. J. Radioanal. Nucl. Chem. 2010, 285, 169–175.
   Web of Science ®Google Scholar
• Lima, L. M.; do Amaral, D. N. Rev. Virtual Quim. 2013, 5 (6), 1075–1100.
   Google Scholar
• Cerecetto, H.; González, M.; Lavaggi, M. L.; Porcal, W. J. Braz. Chem. Soc. 2005, 16, 1290–1296. DOI: 10.1590/S0103-50532005000700030.
   Web of Science ®Google Scholar
• Rayes, S. T. Some Novel Derivatives of Quinoxaline 1,4-Dioxides and Phenazine 7,12-Dioxides. Thesis (M.S.), The American University of Beirut, Lebanon, 2010.
   Google Scholar
• Ermondi, G.; Visentin, S.; Boschi, D.; Fruttero, R.; Gasco, A. J. Mol. Struct. 2000, 523, 149–162. DOI: 10.1016/S0022-2860(99)00386-5.
   Web of Science ®Google Scholar
• Waly, M.; Elgogary, S.; Lashien, A.; Farag, A. J. Heterocyclic Chem. 2015, 52, 411–417. DOI: 10.1002/jhet.1999.
   Web of Science ®Google Scholar
• Barea, C.; Pabón, A.; Pérez-Silanes, S.; Galiano, S.; Gonzalez, G.; Monge, A.; Deharo, E.; Aldana, I. Molecules. 2013, 18, 4718–4727. DOI: 10.3390/molecules18044718.
   PubMed Web of Science ®Google Scholar
• Monge, A.; Palop, J. A.; Piñol, A.; Martínez-Crespo, F. J.; Narro, S.; González, M.; Sáinz, Y.; De Ceráin, A. L.; Hamilton, E.; Barker, A. J. J. Heterocyc Chem. 1994, 31, 1135–1139. DOI: 10.1002/jhet.5570310506.
   Web of Science ®Google Scholar
• (a) Ángel, M.; José, M.; Martínezcrespo, F. J.; Sainz, Y.; Elena, M.; López, A.; Monge, A. 2000, 35, 21–30.
   Google Scholar
  (b) Ortega, M. A.; Morancho, M. J.; Martínez-Crespo, F. J.; Sainz, Y.; Montoya, M. E.; López de Ceráin, A.; Monge, A. Eur. J. Med. Chem. 2000, 35, 21–30. DOI: 10.1016/S0223-5234(00)00112-4.
   PubMed Web of Science ®Google Scholar
• Ewies, E. F.; El-Sayed, N. F.; Boulos, L. S. J Chem Res. 2016, 40, 417–421. DOI: 10.3184/174751916X14655742365588.]
   Google Scholar
• Junnotula, V.; Rajapakse, A.; Arbillaga, L.; López de Cerain, A.; Solano, B.; Villar, R.; Monge, A.; Gates, K. S. Bioorg. Med. Chem. 2010, 18, 3125–3132. DOI: 10.1016/j.bmc.2010.03.042.
   PubMed Web of Science ®Google Scholar
• Moreno-Viguri, E.; Pérez-Silanes, S. Rev. Virtual Quim. 2013, 5, 1101–1119.
   Google Scholar
• Laskina, O. B.; Mel, S. F.; Tselinskii, I. V. Russ. J. Org. Chem. 2012, 48, 278–283. DOI: 10.1134/S1070428012020194.
   Web of Science ®Google Scholar
• Ismail, M. M. F.; Amin, K. M.; Noaman, E.; Soliman, D. H.; Ammar, Y. A. Eur. J. Med. Chem. 2010, 45, 2733–2738. DOI: 10.1016/j.ejmech.2010.02.052.
   PubMed Web of Science ®Google Scholar
• Ancizu, S.; Moreno, E.; Torres, E.; Burguete, A.; Pérez-Silanes, S.; Benítez, D.; Villar, R.; Solano, B.; Marín, A.; Aldana, I.; et al. Molecules. 2009, 14, 2256–2272. DOI: 10.3390/molecules14062256.
   PubMed Web of Science ®Google Scholar
• Sainz, Y.; Montoya, M.; Martínez-Crespo, F.; Ortega, M.; Ceráin, A.; Monge, A. Arzneimittelforschung. 2011, 49, 55–59. DOI: 10.1055/s-0031-1300359.
   Google Scholar
• Martínez Crespo, F. J.; Palop, J. A.; Sainz, Y.; Narro, S.; Senador, V.; González, M.; De Ceráin, A. L.; Monge, A.; Hamilton, E.; Barker, A. J. J. Heterocyc. Chem. 1996, 33, 1671–1677. DOI: 10.1002/jhet.5570330620.
   Web of Science ®Google Scholar
• World Health Organization. Leishmaniasis Fact Sheet N°375. 2014.
   Google Scholar
• Martinez Crespo, F. J.; Palop, J. A.; Saiz, Y.; Narro, S.; Senador, V.; Gonzalez. M; Lopez. A. J. Heterocycl. Chem. 1996, 33, 1671–1677.
   Google Scholar
• Alvar, J.; Velez, I. D.; Bern, C.; Herrero, M.; Desjeux, P.; Cano, J.; Jannin, J.; den Boer, M.; the WHO Leishmaniasis Control Team. PLoS One. 2012, 7, e35671.
   Google Scholar
• Natile, G.; M. Coluccia, M. Coord. Chem. Rev. 2001, 216–217.
   Google Scholar
• Orvig, C.; Abrams, M. J. Chem. Rev. 1999, 99, 2201–2203. DOI: 10.1021/cr980419w.
   PubMed Web of Science ®Google Scholar
• Urquiola, C.; Vieites, M.; Torre, M. H.; Cabrera, M.; Lavaggi, M. L.; Cerecetto, H.; González, M.; Cerain, A. L. d.; Monge, A.; Smircich, P.; et al. Bioorg. Med. Chem. 2009, 17, 1623–1629. DOI: 10.1016/j.bmc.2008.12.064.
   PubMed Web of Science ®Google Scholar
• Kenji, Y.; Hideo, K.; Kazuki, F. J. Nucl. Med. 1999, 40, 5.
   Google Scholar
• Chapman, J. D. Radiother. Oncol. 1991, 20, 13–19. DOI: 10.1016/0167-8140(91)90181-F.
   PubMed Web of Science ®Google Scholar
• Sartorelli, A. C. Cancer Res. 1988, 48, 775–778.
   PubMedGoogle Scholar
• Guyue, C.; Wei, S.; Chen, C.; Liangliang, G.; Haihong, H.; Zhenli, L.; Xu, W.; Zonghui, Y. Front Pharmacol. 2016, 7, 64.
   PubMed Web of Science ®Google Scholar
• Vieira, M.; Pinheiro, C.; Fernandes, R.; Noronha, J. P.; Prudêncio, C. Microbiol. Res. 2014, 169, 287–293. DOI: 10.1016/j.micres.2013.06.015.
   PubMed Web of Science ®Google Scholar
• Cheesman, G. W. H.; Cookson, R. F. In The Chemistry of Heterocyclic Compounds; Weisberger, A., Taylor, E. C., Eds. Wiley Interscience: New York, 1979, Vol. 35.
   Google Scholar