R. J. Collins, B. Ellis, S. B. Hansen
Sep 1, 1951
Citations
0
Influential Citations
16
Citations
Journal
Journal of Pharmacy and Pharmacology
Abstract
IN Part P an attempt was made to define broadly the structural features associated with antibiotic activity in the chloramphenicol series. Since then additional studies have been carried out in this and other laboratories which permit further elaboration of the concepts developed in the earlier publication. The present investigation is concerned largely with the preparation of some analogues of chloramphenicol (I) in which the hydrogen atoms marked a, b and c are replaced by methyl groups. Interpretation of the results obtained is included in the discussion. Experiments on the synthesis of 3-methylchloramphenicol (V ; R = -CHCl,; R’ = -Me) in which Ha of (I) is replaced by Me, have been recorded by Rebstock? who obtained a compound of unknown configuration, hereafter termed the “a”-isomer, by reduction of isonitrosobenzoylacetone, followed by nitration and dichloroacetylation of the resulting amino-alcohol. The asymmetric configuration of the structural type (V), however, provides for the existence of 4 pairs of enantiomorphs, of which 2 pairs may be regarded as derived from erythroand two from threo-2-acetamido1-p-nitrophenylpropane1 : 3-diol. We have, therefore, carried out experiments in order to prepare further compounds of this type.