Chloramphenicol analogues I: DL‐2‐dichloroacetamido‐1‐(4‐pyridyl)‐1,3‐propanediol

Abstract

en Nederlandsche Kininefabriek) .The synthesis of one of the stereoisomeric forms (probably the threo-form) of DL-2-dichloroacetamido-1 ~ (4-pyridyl) -1,3-propanediol, the pyridine analogue of chloramphenicol, is described.Its activity against S a h fyphimuriurn and Eberf. typhi is 1--3 per cent of that of chloramphenicol only.After the structure of chloramphenicol had been established, several analogues were synthesized, in which the nitro group was replaced by other groups or elements 1). As nitrobenzene bears resemblance to pyridine in several respects 2 ) . it was interesting to prepare the pyridine analoaue of chloramphenicol.An attempt to prepare this substance has been published already, though, the project had to be abandoned owing to difficulties encountered in the preparation of the intermediates 1).The simplest way seemed to start from 4-(o-aminoacetyl) -pyridine and to proceed with a reaction scheme more or less similar to those of the syntheses of known chloramphenicol analogues.For the preparation of a sufficiently large amount of the starting aminoketone, the procedure of Burrus and Powell 3 ) did not appear very attractive, nor did the general method via the bromoketone and the hexamethylenetetramine-complex. Clerno 4 ) prepared 2and 3-( o-aminoacetyl) -pyridine by conversion of the 0-p-toluenesulphonyl derivatives of the corresponding acetylpyridine oximes with potassium ethoxide. This very useful and general 1) Cf. e.g. B. N . Feifelson et al., J.

Synthesis, Characterization, and Antimicrobial Studies of Novel Benzodipyran Analog of Chloramphenicol

“…The numerous chemical derivatives of this antibiotic have been synthesized and tested for antimicrobial activity so as to clarify the relationship between the structures of this antibiotic and its biological properties. Because no experimental difficulties were encountered in incorporating the active 2‐dichloroacetamidopropandiol side chain to various heterocyclic systems, many interesting analogs of chloramphenicol have been synthesized to test their antimicrobial properties .…”