ChemInform Abstract: Synthesis of 3′‐Azido‐2′,3′‐dideoxy‐5‐fluorouridine Phosphoramidates and Evaluation of Their Anticancer Activity.

Abstract

Synthesis of 3'-Azido-2',3'-dideoxy-5-fluorouridine Phosphoramidates and Evaluation of Their Anticancer Activity. -The precursor for the target compounds is prepared starting from 5-fluoro-2'-deoxyuridine (I). Compounds (VI) are evaluated for their cytotoxic activity in human cancer cell lines with (VIa) showing highest activity. -(LEWANDOWSKA, M.; RUSZKOWSKI, P.; BARANIAK, D.; CZARNECKA, A.; KLECZEWSKA, N.; CELEWICZ*, L.; Eur. J. Med. Chem. 67 (2013) 188-195, http://dx.doi.org/10.1016/j.ejmech.2013.06.047 ; Fac. Chem., Adam Mickiewicz Univ., PL-60-780 Poznan, Pol.; Eng.) -R. Langenstrassen 05-203

Synthesis, characterization and electrochemical behavior of new bis(fluoroalkyl) ferrocenylphosphonates and their tin tetrachloride complexes

“…FT-IR (υ/cm 19 F NMR (376 MHz, CDCl3) δ -75.10 (t, J = 7.9 Hz). 13 C NMR (101 MHz,CDCl3) 122,73(qd, 1 JC-F = 278.76 Hz, 3…”

“…1 H NMR (400 MHz, CDCl3) δ 4.50 -4.45 (m, 2H), 4.39 -4.34 (m, 2H), 4.27 (s, 5H), 4.10 -3.94 (m, 4H), 1.71 -1.58 (m, 4H), 1.41 -1.21 (m,12H), 0.86 (t, J = 6.7 Hz, 6H). 13 C NMR (101 MHz, CDCl3) 71.50 (d, J = 15.4 Hz, C3), 71.11 (d, J = 13.9 Hz, C2), 69.79 (s, CPC), 66.88 (d, J 1 P-C= 216,14 Hz, C1), 65.64 (d, JP-O-C = 6.0 Hz))., 31.31 (s), 30.48 (d, J = 6.6 Hz), 25.24(s), 22.91 (s), 22.51 (s), 13.97 (s). 31 P NMR (162 MHz, CDCl3) δ 25.79 (s).…”

“…Melting points were measured using an "Electrothermal 9100 : apparatus and are uncorrected. 1 H (300 MHz), 13 C (75.4 MHz), 19 F NMR (282 MHz) and 31 P (121 MHz) NMR spectra were recorded with a Bruker ACIII-300 spectrometer. TMS was used as the internal standard for 1 H and 13 C, CFCl3 for 19 F and H3PO4 for 31 P NMR spectroscopy.…”

“…Organophosphorus chemistry have gained considerable interest due to their widespread applications in various areas such as agriculture [1,2], biology [3,4], pharmaceuticals [5][6][7] and chemical synthesis [8,9]. Among these, one of the most common classes are phosphonates, which are attracting increasing interest as important structural motifs that are found in a variety of naturally occurring compounds [10][11][12], as anticancer [13,14], inhibitors of hepatitis C virus [15,16], anti-HIV [17] and antimalarial agents [18].…”

“…In continuation of our exploration in the synthesis of variously substituted phosphoramidates [34,35], we describe, herein, the synthesis of a series of new fluoroalkyl and alkyl ferrocenylphosphonates and corresponding tin tetrachloride complexes. The products were obtained in good yields and fully characterized by multinuclear ( 1 H, 13 C, 19 F, 31 P and 119 Sn NMR) NMR, IR, cyclic voltammetry (CV), HRMS for phosphonates and elemental analysis for the corresponding tin(IV) complexes. The effect of fluoroalkyl and non-fluorinated long chain groups on the electrochemical behavior of these phosphonate derivatives is also investigated.…”