Fluorinated α-aminoalkylphosphoryl Compounds. Synthesis, Chemical Properties and Biological Activitiy

  • A.Yu. Aksinenko Institute of Physiologically Active Compounds of the Russian Academy of Sciences, 1 Severny proezd, Moscow region, Chernogolovka, 142432 Russia
  • V.B. Sokolov Institute of Physiologically Active Compounds of the Russian Academy of Sciences, 1 Severny proezd, Moscow region, Chernogolovka, 142432 Russia
Keywords: α-aminophosphonates, imines of polyfluoroketones, diazaphospholes, phosphorans, cyanoguanidine, biological activity

Abstract

The review reports data on the synthesis of fluorine-containing α-aminophosphonates based on available organophosphorus and fluoroorganic compounds, some of their chemical properties and biological activity.

References

  1. Kukhar, V. P., Hudson H. R. Aminophosphonic and Aminophosphinic Acids. Chemistry and Biological Activity” (2000). Chichester, John Wiley & Sons Ltd.

  2. Romanenko, V. D., Kukhar, V. P. (2006) Fluorinated Phosphonates:  Synthesis and Biomedical Application, Chem. Rev., 106(9), 3868–3935. DOI

  3. Sokolov, V. B., Aksinenko, A. Yu., Korenchenko, O. V., Martynov I. V. (1989) Reaction of methyldichlorophosphine with the ethoxycarbonylimine of hexafluoroacetone in SO2, Russ. Chem. Bull. 38(5), 1106. DOI

  4. Korenchenko, O. V., Aksinenko, A. Yu., Sokolov, V. B., Martynov I. V. (1991) Reaction of fluorine-containing 1,4,2-oxazaphospholine with OH-nucleophiles, Russ. Chem. Bull. 40(1), 220-222. DOI

  5. Korenchenko, O. V., Aksinenko, A. Yu., Sokolov, V. B., Martynov I. V. (1992) Synthesis of fluorinated 2-Oxo-1,4,5-oxazaphosphol-4-ines and their opening by alcohols. Heteroatom Chem., 3(2), 147-150. DOI

  6. Dmitrieva, N. A., Molchan, O. K., Komissarov, A. A., Sokolov, V. B., Aksinenko, A. Yu., Pushin, A. N., Chekhlov, A. N., Debabov, V. G.(1998) A new inhibitor of pyrimidine phosphorylases, Russ. J. Bioorg. Chem. 24(12), 817-821.

  7. Osipov, S. N., Sokolov, V. B., Kolomiets, A. F., Martynov I. V., Fokin A. V. (1987) Reactions of methyl 2-imino-3,3,3-trifluoropropionates with CH-and PH-acids, Russ. Chem. Bull. 36(5), 1098-1100. DOI

  8. Chekhlov, A. N., Aksinenko, A. Yu., Sokolov, V. B., Martynov I. V. (1991) Sterically strained molecular structure of (1-acetamido-1-trifluoromethyl-2,2,2-trifluoroethyl)diphenylphosphine oxide, Doklady Akademii Nauk SSSR, 319(6), 1396-1400.

  9. Korenchenko, O. V., Ivanov. Yu. Ya., Sokolov, V. B., Martynov I. V. (1992) Synthesis and anticholinesterase activity of fluorine-containing α-aminophosphosphoryl compounds, Pharm. Chem. J. 26(6), 489-492. DOI

  10. Aksinenko, A. Yu., Chekhlov, A. N., Korenchenko, O. V., Sokolov, V. B., Martynov I. V. (1990) Synthesis and structure of O,O-dialkyl-1-(ethoxycarbonyl)-aminohexafluoroisopropyl phosphonate, Zhurnal obshchei khimii 60(1), 61-65.

  11. Chekhlov, A. N., Aksinenko, A. Yu., Sokolov, V. B., Martynov I. V. (1995) Crystal and molecular structures and synthesis of O,O-diisopentyl-1-phenylsulphonamido-1-trifluoromethyl-2,2,2-trifluoroethylphosphonate, Doklady Akademii Nauk 345(3), 360-363.

  12. Martynov I. V., Aksinenko, A. Yu., Chekhlov, A. N., Sokolov, V. B. (1989) Interaction of hexafluoroacetoneimine with PH-acids, Zhurnal obshchei khimii 59(4), 809-811.

  13. Chekhlov, A. N., Aksinenko, A. Yu., Sokolov, V. B., Martynov I. V. (1988) X-Ray diffraction structural investigation of 1-aminohexafluoroisopropyldiphenylphosphine oxide, Russ. Chem. Bull. 37(11), 2363-2364. DOI

  14. Aksinenko, A. Yu., Pushin, A. N., Sokolov V. B. (1993) The easy P-C-bond cleavage of fluorinated phosphine oxide, Phosphorus, Sulfur and Silicon, 84, 249-251. DOI

  15. Kireeva, E. G., Strukova, S. M., Dugina, T. N., Sokolov, V. B., Aksinenko, A. Yu. (1992) Inhibition of enzymatic activity of alpha-thrombin by low molecular weight synthetic inhibitor, Biokhimiia. 57(1), 21-26.

  16. Makhaeva, G. F., Malygin, V. V., Aksinenko, A. Yu., Sokolov, V. B., Strakhova, N. N., Rasdolsky, A. N., Richardson, R. J., Martynov, I. V. (2005) Fluorinated alpha-aminophosphonates - a new type of irreversible inhibitors of serine hydrolases, Dokl. Biochem. Biophys. 400(1-6), 92-95. DOI

  17. Makhaeva G. F., Aksinenko A. Yu., Sokolov V. B., Baskin I. I., Palyulin V. A., Zefirov N. S., Hein N. D., Kampf J. W., Wijeyeskere S. J., Richardson R. J. (2010). Kinetics and mechanism of inhibition of serine esterases by fluorinated aminophosphonates. Chem. Biol. Interact., 187(1-3), 177-184. DOI

  18. Kuusk, V. V., Morozova, I. V., Agabekian, R. S., Aksinenko, A. Yu., Epishina, T. A., Sokolov, V. B., Kovaleva, N. V., Razdol'skiy, A. N., Fetisov, V. N., Martynov, I. V. (1990) Inhibition of cholinesterase activity with fluorine-containing derivatives of alpha-aminophosphonic acid, Bioorg. Khim. 16(11), 1500-1508.

  19. Parfenova, E. V., Popov, D. G., Novikov, A. A., Sterkin, V. E., Strongin, A. Ya., Aksinenko, A. Yu., Korenchenko, O. V., Fetisov, V. I., Martynov, I. V., Sokolov, V. B. (1989) The effect of synthetic proteinase inhibitors of the level of human recombinant proinsulin production, secreted by a genetically engineered strain of Bacillus subtilis, Bioorg. Khim. 15(7), 987-989.

  20. Martynov I. V., Aksinenko, A. Yu., Korenchenko, O. V., Gontar, A. F., Sokolov, V. B. (1988) Phosphorus-containing trifluoromethylureas and their reaction with secondary amines, Russ. Chem. Bull. 37(11), 2359-2360. DOI

  21. Chekhlov, A. N., Aksinenko, A. Yu., Korenchenko, O. V., Sokolov, V. B., Martynov I. V. (1988) Molecular and crystal structure of O,O-diethyl-1-(N-2-trifluoromethylfluoroformamidino)-1-methylethylphosphonate, Doklady Akademii Nauk SSSR 302(4), 855-858.

  22. Aksinenko, A. Yu., Pushin, A. N., Sokolov, V. B., Gontar, A. F., Martynov I. V. (1987) Reaction of α-aminoalkylphosphonates with perfluoro-2-azapropene, Russ. Chem. Bull. 36(5), 1090-1091. DOI

  23. Martynov I. V., Aksinenko, A. Yu., Korenchenko, O. V., Chekhlov, A. N., Fokin, E. A., Sokolov, V. B. (1988) interaction of phosphorus-containing N-trifluoromethylfluoroamidine with N-nucleophiles, Zhurnal obshchei khimii 58(9), 2165-2167.

  24. Chekhlov, A. N., Aksinenko, A. Yu., Sokolov, V. B., Martynov I. V. (1989) Effect of F-hyperconjugation in the structure of O,O-diethyl-1-[(N,N-diisopropylfluoro-formamidino)carbonyl]amino-1-methylpropyl phosphonate, Doklady Akademii Nauk SSSR, 304(2), 400-404.

  25. Martynov I. V., Aksinenko, A. Yu., Chekhlov, A. N., Pushin, A. N., Sokolov, V. B. (1987) New hexacoordinated phosphorus compounds, Russ. Chem. Bull. 36(7), 1559. DOI

  26. Martynov I. V., Chekhlov, A. N., Aksinenko, A. Yu., Sokolov, V. B., Pushin, A. N. (1987) Unusual synthesis and structure of new hexacoordinated phosphorus compounds with 5-membered C2N2P-cycle, Doklady Akademii Nauk SSSR, 297(5) 1132-1136.

  27. Chekhlov, A. N., Martynov I. V., Aksinenko, A. Yu., Sokolov, V. B. (1988) Molecular and crystal structure of a hexacoordinated phosphorus compound,F4PC(R1R2)N(H)C(NR3)2NH (R1 =Me, R2 =i-Bu, R3 =i-Pr), Russ. Chem. Bull. 37(4), 815-817. DOI

  28. Martynov I. V., Aksinenko, A. Yu., Pushin, A. N., Chekhlov, A. N., Fokin, E. A., Sokolov, V. B. (1988) Synthesis and NMR spectra of 5-dialkylamino-2,2,2,2-tetrafluoro-Δ5-1,4,2λ6-diazaphosphoratqlines, Russ. Chem. Bull. 37(9), 1906-1910. DOI

  29. Chekhlov, A. N., Martynov I. V., Aksinenko, A. Yu., Sokolov, V. B. (1989) Molecular structure of new heterocyclic compounds of F4PC(R1R2)N(H)C(NR-2(3))NH hexacoordinated phosphorus, Koordinatsionnaya khimya, 15(9), 1192-1198.

  30. Martynov I. V., Chekhlov, A. N., Aksinenko, A. Yu., Pushin, A. N., Sokolov, V. B., Gontar, A. F. (1987) Synthesis and structure of phosphorus-containing cyanoguanidines, Zhurnal obshchei khimii 57(10), 2285-2289.

  31. Aksinenko, A. Yu., Sokolov, V. B., Korenchenko, O. V., Pushin, A. N., Martynov I. V. (1988) Reaction of a phosphorus-containing N2-trifluoromethyl-N1-methylfluoroamidine with ammonia, Russ. Chem. Bull. 37(7), 1503-1503. DOI

  32. Chekhlov, A. N., Aksinenko, A. Yu., Korenchenko, O. V., Sokolov, V. B., Fokin, E. A., Martynov I. V. (1990) Synthesis and structure of 2-ehtoxy-2-oxo-3,3,4-trimethyl-5-(2-ethoxy-4H-4,4-bis(trifluoromethyl)-2,3,5-oxadiazin-6-yl)imino-1,4,2-diazaphospholane, Zhurnal obshchei khimii 60(8), 1739-1745.

  33. Chekhlov, A. N., Levkovskii, A. V., Aksinenko, A. Yu., Sokolov, V. B., Martynov I. V. (1989) Crystal and molecular structure of 2-ethoxy-2-oxo-3,3,4-trimethyl-5-(cyanoimino)-1,4,2-diazaphospholane, Doklady Akademii Nauk SSSR 309(6), 1410-1413.

  34. Levkovskii, A. V., Aksinenko, A. Yu., Pushin, A. N., Sokolov, V. B., Martynov I. V. (1989) Reaction of a phosphorus-containing N-trifluoromethylfluoroformamidine with methylamine, Russ. Chem. Bull. 38(12), 2631. DOI

  35. Chekhlov, A. N., Levkovskii, A. V., Aksinenko, A. Yu., Sokolov, V. B., Martynov I. V. (1991) Crystal and molecular structure of acetonitrile semisolvate monohydrate of 2-hydroxy-2-oxo-1,3,3,4-tetramethyl-5-(N'.N'-dimethylamidinoformyl) imino-1,4,2-diazaphospholane zwitterion, Doklady Akademii Nauk SSSR 317(6), 1413-1417.

  36. Chekhlov, A. N., Levkovskii, A. V., Aksinenko, A. Yu., Sokolov, V. B., Martynov I. V. (1993) Synthesis and crystal structure of monohydrate zwitterion 3,3,4-trimethyl-5-bis(dimethylamino)-methylenamino-2-oxy-2-oxo-1,4,2-diazaphospholine, Doklady Akademii Nauk 332(3), 338-341.

  37. Martynov I. V., Aksinenko, A. Yu., Chekhlov, A. N., Korenchenko, O. V., Torgun, I. N., Sokolov, V. B. (1989) Interaction of N-substituted cyanoguanidines with hexafluoroacetone, Zhurnal obshchei khimii 59(6), 1397-400.

  38. Chekhlov, A. N., Aksinenko, A. Yu., Sokolov, V. B., Korenchenko, O.V., Martynov I. V. (1988) Crystal and molecular structure of O,O-diethyl-1-(2-(1H)-oxo-3,4-dihydro-4,4-bis(trifluoromethyl)-1,3,5-triazin-6-yl)amino-1-methylpropyl phosphonate, Doklady Akademii Nauk SSSR 300(3), 658-661.

  39. Aksinenko, A. Yu., Sokolov, V. B., Korenchenko, O. V., Chekhlov, A. N., Fokin, E. A., Martynov I. V. (1989) Reaction of phosphorus-containing cyanoguanidines with hexafluoroacetone imines, Russ. Chem. Bull. 38(12), 2580–2583. DOI

  40. Chekhlov, A. N., Aksinenko, A. Yu., Korenchenko, O. V., Sokolov, V. B., Fokin, E. A., Martynov I. V. (1990) Synthesis and structure of 2-ethoxy-2-oxo-3,3,4-trimethyl-5-(2-ethoxy-4H-4,4-bis(trifluoromethyl)-1,3,5-oxadiazin-6-yl)imino-1,4,2-diazaphospholane, Zhurnal obshchei khimii 60(8), 1739-1745.

Published
2018-08-31