FLUOROPHENYL-CONTAINING Α-AMINOPHOSPHONATES: SYNTHESIS AND STRUCTURE
Keywords:
α-aminophosphonates, fluorophenyl, Kabachnik-Fields reaction, synthesis, structureAbstract
Novel α-aminophosphonates 1-3 were synthesized by the one-pot three component reaction of equimolar quantities of dimethylphosphite, diphenylmethylpiperazine and a carbonyl component (4, 3 or 2-fluorobenzaldehyde) in benzene at reflux conditionsfor 30 h viaKabachnik-Fields reaction in high yields (82.9-90.3%). The progress of the reaction was monitored by thin layer chromatography analysis. The chemical structures were established by the physico-chemical methods as IR, 1H, 13C NMR and elemental analyses.
References
[1] Kafaraki P., Lejczak B., Biological Activity of Aminophosphonic Acid//Phosphorus Sulfur Silicon Relat. Elem. 1991. N 63. P. 191.
[2] Panl A.B., Willam B.K. Phosphinic acid dipeptide analogs: potent, slow-binding inhibitors of aspartic peptidases // J. Am. Chem. Soc. 1984. N 106. P. 4282.
[3] Vo-Quang Y., Gravey A. M., Stmonneau, R., Towards new inhibitors of D-alanine:Dalanine ligase: The synthesis of 3-amino butenylphosphonic and aminophosphonamidicacids // Tetrahedron Lett. 1987. N 28. P. 6167.
[4] Baylis E.K., Campbell C.D., Dingwall J.G. 1-Aminoalkylphosphonous acids. Part 1. Isosteres of the protein amino acids // J ChemSoc Perkin Trans 1. 1984. P. 2845-2853.
[5] Prasad G.S., Krishna J.R., Manjunath M., Reddy O.V.S., Krishnaiah M., Reddy C.S., Puranikd V.G., Synthesis, NMR, X-ray crystallography and bioactivity of some α-aminophosphonates // ARKIVOC. 2007. N 13. P. 133.
[6] Jing-Zi L., Bao-An S., Hui-Tao F., Bhadury P.S., Wan W.-T., Yang S., Xu W., Wu J., Jin L.-H., Wei X., Hu D.-Y., Zeng S. Synthesis and in vitro study of pseudo-peptide thioureas containing α-aminophosphonate moiety as potential antitumor agents // Eur. J. Med. Chem. 2010. N 45. P. 5108-5112.
[7] Bloemink M.J., Diederen J.J.H., Dorenbos J.P., Heetebrij R.J., Keppler B.K., Reedijik J., Calcium Ions Do Accelerate the DNA Binding of New Antitumor-Active Platinum Aminophosphonate // Complexes Eur. J. Inorg. Chem. 1999. N 10. P. 1655-1657.
[8] Rao X., Song Z., He L. Synthesis and antitumor activity of novel α-aminophosphonates from diterpenicdehydroabietylamine // Heteroatom. Chem. 2008. N 19. P. 512-516.
[9] Allen M.C., Fuhrer W., Tuck B., Wade R., Wood J.M. Renin inhibitors. Synthesis of transition-state analog inhibitors containing phosphorus acid derivatives at the scissile bond // J. Med. Chem. 1989. Vol. 32, N 7. P. 1652-1661.
[10] Atherton F.R., Hassall C.H., Lambert R.W. Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid // J. Med. Chem. 1986. Vol. 29, N1. P. 29-40.
[11] Hyung-Jun Yoon, Kyoung-Min Park, Won-Jung Choi, Soo-Hee Choi, Jin-Young Park, Jae-Jin Kim, Jeong-Ho Seok. Efficacy and safety of haloperidol versus atypical antipsychotic medications in the treatment of delirium // BMC Psychiatry. 2013. N 13. P. 240.
[12] Sneyd J.R. Droperidol: past, present and future // Anaesthesia. 2009. N 64. P. 1161–1164. doi:10.1111/j.1365-2044.2009.06124.x
[13] Sumiyoshi T., Jayathilake K., Meltzer H.Y. The effect of melperone, an atypical antipsychotic drug, on cognitive function in schizophrenia // Schizophrenia Research. 2003. Vol. 59, N 1. P. 7-16.
[14] Groult H., Leroux F., Tressaud A. Modern Synthesis Processes and Reactivity of Fluorinated Compounds: Progress in Fluorine Science. London: Academic Press, 2016. P. 500-501.
[15] Bohm H.J., Banner D., Bendels S., Kansy M., Kuhn B., Muller K., Obst-Sander U., Stahl M. Fluorine in Medicinal Chemistry // ChemBioChem: Wiley-VCH Verlag GmbH & Co. KGaA. Weinheim. 2004. Vol. 5, N 5. P. 637-643.
[16] Strunecka A., Patocka J., Connett P. Fluorine in medicine // Journal of Applied Biomedicine. 2004. N 2. P. 141-150.
[17] Kabachnik M.I., Bear T.Ya. A new method for the synthesis of α-aminophosphonic acids. Doklady Akademii Nauk SSSR. 1952. P. 689.
[18] Fields Е.K. Substituted hydroxymethanephosphonic esters // J. Am. Chem. Soc. 1952. Vol. 74, N 6. P. 1528-1531.
[19] Akhmetova G.S., Ibraimbek A.K., Sadyrbaeva F.M., Otesh A., Yu V.K., Praliev K.D., Ilyin A.I., Leonova N.V., Seilkhanov T.M., Idrisova R. 1-(2-Phenylethyl)-4-ketoximipiperidine fluorobenzoate with antimicrobial activity // News of Scientific and Technical Society "Kazakh". Ser. chem. 2015. N 3. P. 4-9.