Facile synthesis of some new functionalized 2-selenoxopyrimidines

References

• Garud, D. R.; Koketsu, M.; Ishihara, H. Isoselenocyanates: A Powerful Tool for the Synthesis of Selenium-Containing Heterocycles. Molecules 2007, 12, 504–535. DOI: 10.3390/12030504.
   PubMed Web of Science ®Google Scholar
• Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V. Comprehensive Heterocyclic Chemistry II. A Review of the Literature 1982–1995; Elsevier Science: Oxford, 1996; Vol. 1–11.
   Google Scholar
• Wirth, T. Organoselenium Chemistry: Modern Development in Organic Synthesis, Selenocarbonyls; Springer: Berlin, 2000; pp 178–193.
   Google Scholar
• Pfeiffer, W. D.; Romberg, H.; Kelzhanova, N.; Saginayev, A. T.; Villinger, A.; Langer, P. Synthesis and Reactions of 1,3,4-Selenadiazines. Heterocycles 2014, 8, 1397–1431. DOI: 10.3987/COM-13-S(S)109.
   Google Scholar
• Bodtke, A.; Kandt, M.; Pfeiffer, W. D.; Langer, P. Synthesis of 4-Aryl-2-Imino-2H-Selenazolines by a Reaction of α α-(Selenocyanato)Acetophenones with Anilines. Phosphorus Sulfur Silicon Relat. Elem. 2007, 182, 209–217. DOI: 10.1080/10426500600892685.
   Web of Science ®Google Scholar
• Below, H.; Pfeiffer, W. D.; Geisler, K.; Lalk, M.; Langer, P. 1,3-Selenazole. Eur. J. Org. Chem. 2005, 2005, 3637–3639. DOI: 10.1002/ejoc.200500456.
   Web of Science ®Google Scholar
• Geisler, K.; Künzler, A.; Below, H.; Bulka, E.; Pfeiffer, W. D.; Langer, P. Synthesis and Reactivity of 2-Acyl-1,3-Selenazoles. Synthesis 2004, 97–105. DOI: 10.1055/s-2003-44348.
   Web of Science ®Google Scholar
• Bhabak, K. P.; Mugesh, G. Functional Mimics of Glutathione Peroxidase: Bioinspired Synthetic Antioxidants. Acc. Chem. Res. 2010, 43, 1408–1419. DOI: 10.1021/ar100059g.
   PubMed Web of Science ®Google Scholar
• Alberto, E. E.; Do Nascimento, V.; Braga, A. L. Catalytic Application of Selenium and Tellurium Compounds as Glutathione Peroxidase Enzyme Mimetics. J. Braz. Chem. Soc. 2010, 21, 2032–2041. DOI: 10.1590/S0103-50532010001100004.
   Web of Science ®Google Scholar
• Sinha, R.; El-Bayoumy, K. Apoptosis is a Critical Cellular Event in Cancer Chemoprevention and Chemotherapy by Selenium Compounds. Curr. Cancer Drug Targets 2004, 4, 13–28. DOI: 10.2174/1568009043481614.
   PubMed Web of Science ®Google Scholar
• Rikiishi, H. Apoptotic Cellular Events for Selenium Compounds Involved in Cancer Prevention. J. Bioenerg. Biomembr. 2007, 39, 91–98. DOI: 10.1007/s10863-006-9065-7.
   PubMed Web of Science ®Google Scholar
• Nam, K. N.; Koketsu, M.; Lee, E. H. 5-Chloroacetyl-2-Amino-1,3-Selenazoles Attenuate Microglial Inflammatory Responses through NF-κB Inhibition. Eur. J. Pharmacol. 2008, 589, 53–57. DOI: 10.1016/j.ejphar.2008.03.034.
   PubMed Web of Science ®Google Scholar
• Choi, S. Y.; Jo, Y. O.; Koketsu, M.; Ishihara, H.; Kim, S. H.; Kim, S. Y. Inhibitory Effects of 2-(4-Chlorophenyl)-1,3-Selenazol-4-One on Lipopolysaccharide-Induced Nitric Oxide Production in RAW 264.7 Cells. J. Korean Soc. Appl. Biol. Chem. 2009, 52, 371–374. DOI: 10.3839/jksabc.2009.066.
   Google Scholar
• El-Bayoumy, K.; Sinha, R. Mechanisms of Mammary Cancer Chemoprevention by Organoselenium Compounds. Mutat. Res. 2004, 551, 181–197. DOI: 10.1016/j.mrfmmm.2004.02.023.
   PubMed Web of Science ®Google Scholar
• Block, E.; Bird, S.; Tyson, J. F.; Uden, P. C.; Zhang, X.; Denoyer, E. The Search for Anticarcinogenic Organoselenium Compounds from Natural Sources. Phosphorus Sulfur Silicon Relat. Elem. 1998, 136, 1–10. DOI: 10.1080/10426509808545931.
   Web of Science ®Google Scholar
• Ahn, H. J.; Koketsu, M.; Yang, E. M.; Kim, Y. M.; Ishihara, H.; Yang, H. O. 2‐(4‐Methylphenyl)‐1,3‐Selenazol‐4‐One Induces Apoptosis by Different Mechanisms in SKOV3 and HL 60 Cells. J. Cell. Biochem. 2006, 99, 807–815. DOI: 10.1002/jcb.20973.
   PubMed Web of Science ®Google Scholar
• Nishina, A.; Sekiguchi, A.; Fukumoto, R.; Koketsu, M.; Furukawa, S. Selenazoles (Selenium Compounds) Facilitate Survival of Cultured Rat Pheochromocytoma PC12 Cells after Serum-Deprivation and Stimulate Their Neuronal Differentiation via Activation of Akt and Mitogen-Activated Protein Kinase, Respectively. Biochem. Biophys. Res. Commun. 2007, 352, 360–365. DOI: 10.1016/j.bbrc.2006.11.025.
   PubMed Web of Science ®Google Scholar
• Koketsu, M.; Choi, S. Y.; Ishihara, H.; Lim, B. O.; Kim, H.; Kim, S. Y. Inhibitory Effects of 1,3-Selenazol-4-One Derivatives on Mushroom Tyrosinase. Chem. Pharm. Bull. 2002, 50, 1594–1596. DOI: 10.1248/cpb.50.1594.
   PubMed Web of Science ®Google Scholar
• Lee, E. H.; Lim, Y. J.; Ha, S. K.; Kang, T. H.; Koketsu, M.; Kang, C. H.; Kim, S. Y.; Park, J. H. Inhibitory Effects of 5‐Chloroacetyl‐2‐Piperidino‐1,3‐Selenazole, a Novel Selenium‐Containing Compound, on Skin Melanin Biosynthesis. J. Pharm. Pharmacol. 2010, 62, 352–359. DOI: 10.1211/jpp.62.03.0010.
   PubMed Web of Science ®Google Scholar
• Tulenin, S. S.; Markov, V. F.; Maskaeva, L. N.; Kuznetsov, M. V. Deposition Conditions, Composition, and Structure of Chemically Deposited In2Se3 Films. Russ. J. Inorg. Chem. 2016, 61, 488–495. DOI: 10.1134/S0036023616040227.
   Google Scholar
• Sogabe, S.; Ando, H.; Koketsu, M.; Ishihara, H. A Novel Dechloroacetylation Reagent: 1-Seleonocarbamoylpiperidine. Tetrahedron Lett. 2006, 47, 6603–6606. DOI: 10.1016/j.tetlet.2006.07.009.
   Web of Science ®Google Scholar
• Takahashi, H.; Nishina, A.; Fukumoto, R. H.; Kimura, H.; Koketsu, M.; Ishihara, H. Selenoureas and Thioureas Are Effective Superoxide Radical Scavengers in Vitro. Life Sci. 2005, 76, 2185–2192. DOI: 10.1016/j.lfs.2004.08.037.
   PubMed Web of Science ®Google Scholar
• Olsen, J. I.; Plata, G. B.; Padrón, J. M.; López, Ó.; Bols, M.; Fernández-Bolaños, J. G. Selenoureido-Iminosugars: A New Family of Multitarget Drugs. Eur. J. Med. Chem. 2016, 123, 155–160. DOI: 10.1016/j.ejmech.2016.07.021.
   PubMed Web of Science ®Google Scholar
• Romero-Hernandez, L. L.; Merino-Montiel, P.; Montiel-Smith, S.; Meza-Reyes, S.; Vega-Báez, J. L.; Abasolo, I.; Schwartz, S.; López, O.; Fernández-Bolaños, J. G. Diosgenin-Based Thio(Seleno)Ureas and Triazolyl Glycoconjugates as Hybrid Drugs. Antioxidant and Antiproliferative Profile. Eur. J. Med. Chem. 2015, 99, 67–81. DOI: 10.1016/j.ejmech.2015.05.018.
   PubMed Web of Science ®Google Scholar
• Merino-Montiel, P.; Maza, S.; Martos, S.; López, Ó.; Maya, I.; Fernández-Bolaños, J. G. Synthesis and Antioxidant Activity of O-Alkyl Selenocarbamates, Selenoureas and Selenohydantoins. Eur. J. Pharm. Sci. 2013, 48, 582–592. DOI: 10.1016/j.ejps.2012.12.016.
   PubMed Web of Science ®Google Scholar
• Ibáñez, E.; Plano, D.; Font, M.; Calvo, A.; Prior, C.; Palop, J. A.; Sanmartín, C. Synthesis and Antiproliferative Activity of Novel Symmetrical Alkylthio- and Alkylseleno-Imidocarbamates. Eur. J. Med. Chem. 2011, 46, 265–274. 2010.11.013. DOI: 10.1016/j.ejmech.
   PubMed Web of Science ®Google Scholar
• Pfeiffer, W. D.; Ahlers, K. D.; Falodun, A.; Villinger, A.; Langer, P. Synthesis and Spectroscopic Characterization of Arylated Selenoureas. Phosphorus Sulfur Silicon Relat. Elem. 2014, 189, 324–332. DOI: 10.1080/10426507.2013.820729.
   Web of Science ®Google Scholar
• Geisler, K.; Pfeiffer, W. D.; Künzler, A.; Below, H.; Bulka, E.; Langer, P. Synthesis of 1,3-Selenazoles and Bis(Selenazoles) from Primary Selenocarboxylic Amides and Selenourea. Synthesis 2004, 875–884. DOI: 10.1055/s-2004-822312.
   Web of Science ®Google Scholar
• Klein, E.; De Bonis, S.; Thiede, B.; Skoufias, D.; Kozielski, F.; Lebeau, L. New Chemical Tools for Investigating Human Mitotic Kinesin Eg5. Bioorg. Med. Chem. 2007, 15, 6474–6488. DOI: 10.1016/j.bmc.2007.06.016.
   PubMed Web of Science ®Google Scholar
• Kolb, S.; Mondesert, O.; Goddard, M. L.; Jullien, D.; Villoutreix, B. O.; Ducommun, B.; Garbay, C.; Braud, E. Development of Novel Thiazolopyrimidines as CDC25B Phosphatase Inhibitors. Chem. Med. Chem. 2009, 4, 633–648. DOI: 10.1002/cmdc.200800415.
   Web of Science ®Google Scholar
• Schneider, M.; Gil, M. J.; Reliquet, A.; Meslin, J. C.; Levillain, J.; Vazeux, M.; Jury, D.; Mieloszynski, J. L.; Paquer, D. Correlations Des DéPlacements Chimiques En Rmn 13C De Composés Carbonyles, Thiocarbonyles Et Selenocarbonyles. Phosphorus Sulfur Silicon Relat. Elem. 1998, 134, 295–305. DOI: 10.1080/10426509808545470.
   Web of Science ®Google Scholar
• Antoniadis, C. D.; Hadjikakou, S. K.; Hadjiliadis, N.; Papakyriakou, A.; Baril, M.; Butler, I. S. Synthesis and Structures of Se Analogues of the Antithyroid Drug 6‐n‐Propyl‐2‐Thiouracil and Its Alkyl Derivatives: Formation of Dimeric Se–Se Compounds and Deselenation Reactions of Charge‐Transfer Adducts of Diiodine. Chem. Eur. J. 2006, 12, 6888–6897. DOI: 10.1002/chem.200501455.
   PubMed Web of Science ®Google Scholar
• Mautner, H. G.; Clayton, E. M. 2-Selenobarbiturates. Studies of Some Analogous Oxygen, Sulfur and Selenium Compounds. J. Am. Chem. Soc. 1959, 81, 6270–6273. DOI: 10.1021/ja01532a037.
   Web of Science ®Google Scholar
• Diao, P. C.; Lin, W. Y.; Jian, X. E.; Li, Y. H.; You, W. W.; Zhao, P. L. Discovery of Novel Pyrimidine-Based Benzothiazole Derivatives as Potent Cyclin-Dependent Kinase 2 Inhibitors with Anticancer Activity. Eur. J. Med. Chem. 2019, 179, 196–207. DOI: 10.1016/j.ejmech.2019.06.055.
   PubMed Web of Science ®Google Scholar
• Baryshnikov, G. V.; Minaeva, V. A.; Minaev, B. F.; Sun, V. H.; Grigoras, M. Analysis of the Electronic, IR, and 1H-NMR Spectra of Conjugated Oligomers Based on 4,4'-Triphenylamine Vinylene. Opt. Spectrosc. 2016, 121, 348–356. DOI: 10.1134/S0030400X16090046.
   Web of Science ®Google Scholar
• Karaush, N. N.; Minaeva, V. A.; Baryshnikov, G. V.; Minaev, B. F.; Ågren, H. Identification of Tautomeric Intermediates of a Novel Thiazolylazonaphthol Dye-A Density Functional Theory Study. Spectrochim. Acta Part A 2018, 203, 324–332. DOI: 10.1016/j.saa.2018.05.096.
   PubMed Web of Science ®Google Scholar
• Panda, S. S.; Khanna, P.; Khanna, L. Biginelli Reaction: A Green Perspective. Curr. Org. Chem. 2012, 16, 507–520. DOI: 10.2174/138527212799499859.
   Web of Science ®Google Scholar
• Nagarajaiah, H.; Mukhopadhyay, A.; Moorthy, J. N. Biginelli Reaction: An Overview. Tetrahedron Lett. 2016, 57, 5135–5149. DOI: 10.1016/j.tetlet.2016.09.047.
   Web of Science ®Google Scholar
• Chen, P.; Tu, M. Synthesis of 2-Selenoxo DHPMs by Biginelli Reaction with Hf(OTf)4 as Catalyst. Tetrahedron Lett. 2018, 59, 987–990. DOI: 10.1016/j.tetlet.2018.01.070.
   Web of Science ®Google Scholar
• Barbosa, F. A. R.; Siminski, T.; Canto, R. F. S.; Almeida, G. M.; Mota, N. S. R. S.; Ourique, F.; Pedrosa, R. C.; Braga, A. L. Novel Pyrimidinic Selenourea Induces DNA Damage, Cell Arrest and Apoptosis in Human Breast Carcinoma. Eur. J. Med. Chem. 2018, 155, 503–515. DOI: 10.1016/j.ejmech.2018.06.026.
   PubMed Web of Science ®Google Scholar