1498-56-2Relevant academic research and scientific papers
Synthesis, characterization, and structures of zinc(II) and cadmium(II) complexes with phosphoramides bearing cyclic amino groups
M’haiham, Mohamed,Ebeid, Khaled,Ebnou, Fatimetou,Carpenter-Warren, Cameron L.,Slawin, Alexandra M. Z.,Woollins, John Derek,Ben Dhia, Med Taieb,Sanhoury, Med Abderrahmane K.
, p. 453 - 466 (2020)
Twelve new zinc(II) and cadmium(II) complexes with symmetric ligands, [MCl2((R2N)3PO)2] (M = Zn, R2N = pyrrolidinyl (1), piperidinyl (2); M = Cd, R2N = pyrrolidinyl (3), piperidinyl (4)), and differently substituted ligands of the general formula [MCl2(R2N)PO(R’2N)2] (M = Zn or Cd; R2N = Pyrr, Pip or Mor; R’2N = Pyrr, Pip or Mor (5–12) have been synthesized from reaction of zinc(II) or cadmium(II) chlorides with the ligands, giving yields of 43–76%. The complexes were characterized with multinuclear (1H, 13C and 31P) NMR, conductivity, IR spectroscopy, and X-ray analyses. Complexes 1, 3, 11, and 12 are comprised of two ligands coordinated to the metal center in a distorted monomeric tetrahedral arrangement. The P = O bond lengths of 1.490(3) (1), 1.497(4) (3), 1.480(4) (11), and 1.479(5) ? (12) are in the order observed for analogous phosphoramide complexes. The results are compared with those reported for related chalcogen counterparts.
Hydrolysis of cyclic phosphoramides. Evidence for syn lone pair catalysis
Nunez, Andres,Berroteran, Dyanna,Nunez, Oswaldo
, p. 2283 - 2289 (2007/10/03)
Hydrolysis between 1.5 31PNMR spectroscopy. The observed rates fit the equation: kobs = kH2O[H+]/([H+] + Ka) + k′su
Synthesis of P-chiral enephosphonic acid derivatives
Grison, Claude,Comoy, Corinne,Chatenet, David,Coutrot, Philippe
, p. 83 - 97 (2007/10/03)
An efficient and convenient synthesis of chiral enephosphonic acid derivatives (enephosphonates, enephosphonamides, enephosphinates) was reported by a two-step procedure involving alkylidenediphosphorylation of nucleophiles followed by a Horner-Emmons olefination. Depending on the selected strategy, the synthesis could be executed according to a one-pot or a twostep reaction sequence. Regioselectivity of Horner-Emmons reaction and 31P-NMR study of diphosphorylated anions were described.
Synthesis and Biological Evaluation of 5-Fluoro-2'-deoxyuridine Phosphoramidate Analogs
Fries, Kristin M.,Joswig, Carolyn,Borch, Richard F.
, p. 2672 - 2680 (2007/10/03)
A series of alkylating phosphoroamidate analogs of 5-fluoro-2'-deoxyuridine has been prepared and their growth inhibitory activity evaluated against murine L1210 leukemia and B16 melanoma cells in vitro.These compounds were designed to undergo intracellular release of the phosphoramidate anions, which it was hoped would function as irreversible inhibitors of thymidylate synthase.The expectation was that binding of the nucleoside moiety would be followed by alkylation of the enzyme via the phosphoramidate.The chloride, bromide, iodide, and tosylate analogs were highlypotent inhibitors of L1210 cell proliferation, with increased inhibition observed at both higher drug concentrations and longer exposure times.Addition of thymidine completely reversed the inhibition for all compounds, suggesting that these compounds are acting via inhibition of thymidylate synthase.Although the nonalkylating morpholine analog 1f was ca. 50-fold less potent than the methyl(chloroethyl)amino compound, the piperidine analog 1g was only 2-fold less potent, confirming that nitrogen basicity may be as important as the presence of an alkylating group.Addition of thymidine reversed the growth inhibition of the morpholine and piperidine analogs, suggesting that these compounds may also undergo intracellular conversion to 5-fluoro-2'-deoxyuridine 5'-monophosphate.The thymidine and deoxyuridine derivatives 2 and 3 showed minimal growth inhibition in the L1210 assay.The alkylating analogs showed modest cytotoxicity against B16 melanoma cells, and the potency of the analogs was more dependent upon the alkylating moiety than on the 5-substituent.
