How to cite this paper
Golovchenko, O., Abdurakhmanova, E., Brusnakov, M., Vladimirov, S., Shyshatska, Y., Khilya, O., Volovenko, Y & Brovarets, V. (2020). Synthesis of novel phosphorylated peptidomimetics which contain ω-haloalkyl and ω-thiocyanoethyl residues.Current Chemistry Letters, 9(3), 131-142.
Refrences
1. Kachaeva M., Pilyo S., Popilnichenko S., Kornienko A., Rusanov E., Prokopenko V., Zyabrev V., Brovarets V. (2018) Synthesis of fused heterocycles from 2-aryl-5-(chlorosulfonyl)oxazole-4-carboxylates and α-aminoakoles involving the Smiles rearrangement. Curr. Chem. Lett. 7 (4) 101-110.
2. Chumachenko S. A., Shablykin O. V., Vasilenko A. N., Brovarets V. S. (2013) Recyclization of 2-methoxy-5-morpholino-1,3-oxazole-4-carbonitrile by benzylamine, phenethylamine, and phenylhydrazine. Russ. J. Gen. Chem. 83 (9) 1710–1715.
3. Kornienko A. N., Pil'o S. G., Prokopenko V. M., Brovarets V. S. (2014) Amidophenacylating reagents in synthesis of new derivatives of 1,3-oxazole- and 1,3-thiazole-4-sulfonyl chlorides and corresponding sulfonamides. Russ. J. Gen. Chem. 84 (4) 686-692.
4. Kornienko A. N., Pil'o S. G., Prokopenko V. M., Brovarets V. S. (2014) Synthesis and properties of 2-substituted 5-chloro-1,3-oxazole-4-carboxamides. Russ. J. Gen. Chem. 84 (6) 1186-1189.
5. Kornienko A. N., Pil'o S. G., Prokopenko V. M., Brovarets V. S. (2014) Synthesis of methyl 2-aryl-5-chlorosulfonyl-1,3-oxazole-4-carboxylates and their reactions with amines and amidines. Russ. J. Gen. Chem. 84 (8) 1555-1560.
6. Kornienko A. N., Pil'o S. G., Kozachenko A. P., Prokopenko V. M., Rusanov E. B., Brovarets V. S. (2014) Reaction of 2-Aryl-4-Cyano-1,3-Oxazole-5-Sulfonyl Chlorides With 5-Amino-1H-Pyrazoles and 5-Amino-1H-1,2,4-Triazole. Chem. Heterocycl. Compd. 50 (1) 76-86.
7. Shablykin O.V., Brovarets V.S., Rusanov E.B., Drach B.S. (2007) Peculiar Reaction of N2 -Acyl-5-hydrazino-1,3-oxazole-4-carbonitriles with the Lawesson Reagent. Heteroatom Chem. 18 (7) 782-785.
8. Shablykin O.V., Gakh A.A., Brovarets V.S., Rusanov E.B., Drach B.S. (2008) A Facile Synthesis of New 1,2-Dihydro-2λ5 -[1,3]oxazolo[5,4-d][1,3,2]diaza¬phosphi¬nine Derivatives Starting from 2-Benzoylamino-3,3-dichloroacrylonitrile. Heteroatom Chem. 19 (5) 506-511.
9. Shablykin O.V., Golovchenko A.V., Brovarets V.S., Drach B.S. (2007) Reaction of 2-aryl(methyl)-4-cyano-5-hydrazino-1,3-oxazoles with aryl Isothiocyanates. Russ. J. Gen. Chem. 77 (5) 932-935.
10. Shablykin O.V., Brovarets V.S., Drach B.S. (2007) New transformations of 5-Hydrazino-2-phenyl-1,3-oxazole-4-carbonitrile. Russ. J. Gen. Chem. 77 (5) 936-939.
11. Turchi I. J. (1986) The Chemistry of Heterocyclic Compounds, J.Willey and Sons, New York, vol.45.
12. Palmer D. C. (2003) Oxazoles: Synthesis, Reactions and Spectroscopy, Hoboken, John Willey, New Jersey.
13. Golovchenko A.V., Prokopenko V. M., Shablykin O. V., Zyabrev V.S., Brovarets V.S. (2014) In the Chemistry and biological activity of azoles (Eds: V.S. Brovarets, V.S. Zyabrev), LAP LAMBERT Academic Publ., Germany, Ch. 6.
14. Kondratyuk K.M., Lukashuk E.I., Golovchenko A.V., Brovarets V.S. (2012) Reaction of diethyl 1-acylamino-2,2-dichloroethenylphosphonates with amino acids esters. Russ. J. Gen. Chem. 82 (4) 643–651.
15. Kondratyuk K.M., Lukashuk O.I., Golovchenko A.V., Komarov I.V., Brovarets V.S., Kukhar V.P. (2013) Synthesis of 5-amino-2-aminoalkyl-1,3-oxazol-4-ylphosphonic acid derivatives and their use in the preparation of phosphorylated peptidomimetics. Tetrahedron 69 (30) 6251-6261.
16. Lukashuk O.I., Kondratyuk K.M., Golovchenko A.V., Brovarets V.S., Kukhar V.P. (2013) A Novel Synthetic Approach to Phosphorylated Peptidomimetics. Heteroatom Chem. 24 (4) 289–297.
17. Lukashuk O.I., Abdurakhmanova E.R., Kondratyuk K.M., Golovchenko A.V., Brovarets V.S., Kukhar V.P. (2015) Introduction of chiral 2-(aminoalkyl) substituents into 5-amino-1,3-oxazol-4-ylphosphonic acid derivatives and their use in phosphonodipeptide synthesis. RSC Advances 71 (5) 11198-11206.
18. Abdurakhmanova E.R., Lukashuk E.I., Golovchenko A.V., Brovarets V.S. (2016) Synthesis of Novel Phosponopeptidomimetics. Rus. J. Gen. Chem. 86 (5) 1206-1208.
19. Abdurakhmanova E.R., Lukashuk E.I., Golovchenko A.V., Brovarets V.S. (2016) Synthesis and Properties of 4-Phosphorylated Derivatives of 5-Hydroxyalkylamino-1,3-Oxazoles. Rus. J. Gen. Chem. 86 (7) 1584-1596.
20. Greco M.N., Hawkins M.J., Powell E.T., Almond H.R., de Garavilla L., Hall J., Minor L.K., Wang Y., Corcoran T.W., Di Cera E., Cantwell A.M., Savvides S.N., Damiano B.P., Maryanoff B.E. (2007) Discovery of Potent, Selective, Orally Active, Nonpeptide Inhibitors of Human Mast Cell Chymase. J. Med. Chem. 50 (8) 1727-1730.
21. Kunze T. (1996) Phosphono Analogues of Glutathione as New Inhibitors of Glutathione S-Transferases. Arch. Pharm. 329 (11) 503-509.
22. Kunze T., Heps S. (2000) Phosphono Analogs of Glutathione: Inhibition of Glutathione Transferases, Metabolic Stability, and Uptake by Cancer Cells. Biochem. Pharm. 59 (8) 973-981.
23. Sperandio D., Gangloff A., Litvak J., Goldsmiss R., Hataye J.M., Wang V.R., Shelton E.J., Elrod K., Janc J.W., Clark J.M., Rice K., Weinheimer S., Yeung K.-S., Meanwell N.A., Hernandes D., Staab A.J., Venables B.L., Spencer J.R. (2002) Highly Potent Non-peptidic Inhibitors of the HCVNS3/NS4A Serine Protease. Bioorg. Med. Chem. Lett. 12 (21) 3129-3133.
24. Nizhenkovska I.V., Romanenko A.V., Sedko K.V., Grusha M.M., Brovarets V.S., Golovchenko A.V. (2015) Studing of vasoactive properties of diethyl ester of 5-alkylamino-2-{N-[N-benzoyl(4-methylbenzal)-glycyl]¬amino¬methyl}-1,3-oxazole-4-ylphosphonic acid on rat´s isolated aorta. Pharm. Drug Toxycol. 46 76-83.
25. Nizhenkovska I.V., Sedko K.V., Golovchenko O.V., Golovchenko O.I. (2018) Studies of acute toxicity of 1,3-oxazole-4-ylphosphonic acid derivative in intraperitoneal administration. Visnik Farmacii 93 43-48.
26. Nizhenkovska I., Sedko K., Golovchenko O., Golovchenko O. (2018) Efficiency of the application 1,3-oxazole-4-ylphosphonic acid derivative on the sustained arterial hypertension model in rats. Curr. Topics Pharm. 22 63-68.
27. Kim D., Benjamim L., Horenstein A.,Nakanishi K. (1990) Synthesis of tunichromes Mm-1 and Mm-2, blood pigments of the iron-assimilating tunicate, Molgula Manhattensis. Tetrahedron Lett. 31 (49) 7119-7122.
28. Horenstein B.A., Nakanishi K. (1989) Synthesis of Unprotected
(±)-Tunichrome An-1, a Tunicate Blood Pigment. J. Am. Chem. Soc. 111 (16) 6242–6246.
29. Schmidt U., WildJ. (1985) Totalsynthese von Hexaacetylcelenamid A. Liebigs Ann. Chem. 9 1882-1894.
30. Schmidt U., Wild J. (1984) Total synthese von Hexaacetylcelenamid A. Angew. Chem. 96 996-998.
31. Armstrong R.W., Tellew J.E., Moran E. (1996) Mono-Osmylation Acid Dienes: Synthesis of Dehydroamino Acids Related to the Azinomycins. Tetrahedron Lett. 37 (4) 447-450.
32. Coleman R.S., Li J., Navarro A. (2001) Total Synthesis of Azinomycin A. Angew. Chem. Int. Ed. 40 (9) 1736-1739.
33. Schmidt U., Riedl B. (1993) The Total Synthesis of Antrimycin Dv; III: Construction of the Protected Hexapeptide and Deprotection. Synthesis 12 815-818.
34. Köckritz A., Schnell M. (1993) α-Substituted phosphonates 68. α-Aminophosphonates and phosphonosubstituted heterocycles from diethyl [2,2,2-trichloro-1-iso¬cyanatoethyl]phosphonate. Phosphorus, Sulfur, Silicon, Relat. Elem. 83 (1-4) 125-134.
35. Röhr G., Schnell M., Köckritz A. (1992) α-Substituted phosphonates; synthesis of 2-phosphonoglycine amides by solvolysis of 5-amino-4-phosphonooxazoles. Synthesis 10 1031–1034.
36. Salehi P., Zolligol M.A., Shirini F., Baghbanzadeh M. (2006) Silica sulfuric acid and silica chloride as efficient reagents for organic reactions. Curr. Org. Chem. 10 2171-2189.
37. KlimovaV.A. (1975) Basic Micromethods for the Analysis of Organic Compounds [in Russian], Moscow, USSR: Khimiya.