By Irving Wainer
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Extra info for Drug stereochemistry. Amalythical methods and pharamacology
We also found that the 2-fluoroethyl esters of some of the higher w-fluorocarboxylic acids had a greater toxicity than expected from a consideration solely of the hydrolysis products. Taylor: The increased toxicity might be connected with transport to a particular site. Saunders: Yes, that is the explanation we gave. We often find this in the phosphorofluoridate series : phosphorofluoroidic acid is non-toxic, but the esters (I) are toxic. /OR /OR O=P-OR O=P-F \F F' /OR O=P-OH F' I think that when there are two fluorine atoms in the phosphate molecule (11), one fluorine hydrolyses quickly to OH and the new molecule (III) does not then get through the plasma membrane.
STACEY and I. G. WILDING(1949) J. Chem. 773. SWARTS, F. (1896) Bull. Chim. BeZg. 15, 1134. Discussion Gdl: Is it likely that the inductive effects in P-fluoropropionic acid lower the bond energy of C-F enough to allow exchange of F for OH to occur in cold alkaline conditions? Saunders: The fluorobutyrates appear to have more stability. Could it be the loss of H F in much the same way as hydracrylic acid goes to acrylic acid so easily with the loss of water, whereas lactic acid does not behave in the same way?
And T. SAKAI(1971) Biochemistry 10, 3598. , S. ROZENand E. D. BERGMANN (1971) J. Org. Chem. 36,501. WEISSMAN, A. and B. K. KOE(1967) J. Pharmacol. Exp. Ther. 155, 135-144. Carbon-Fluorine Compounds Chemistry, Biochemistry & Biological Activities KATHERINE ELLIOTT and JOANBIRCH Copyright 0 Ciba Foundation The physical properties of the carbon-fluorine bond A. G . SHARPE University Chemical Laborutory, Cambridge This paper deals with the fundamental physicochemical properties of compounds containing the C-F (carbon-fluorine) bond.
Drug stereochemistry. Amalythical methods and pharamacology by Irving Wainer