Among over 2000 synthesized compounds of the structure similar to chloramphenicol [1], only three found use in therapy: thiamphenicol, azidamphenicol and florfenicol. The heteroaromatic analogs of chloramphenicol are insignificantly active or inactive. The only exception is the thiophene analogue with the activity of 50% in relation to the racemic chloramphenicol.

Pyrrole analogs of chloramphenicol are known to exhibit the selective significant activity only against strains from the Enterobacteriaceae family and high activity against Gram-positive and Gram-negative bacteria [2,3].

The synthesis of comound 5 was performed according to the procedure showen in the scheme below.

Reagents and conditions: (a) CHF₂COOH, SOCl₂, Et₃N, temp. 0 ^oC, THF; (b) HCHO, NaHCO₃, EtOH; (c) (i-PrOH)₃Al, i-PrOH

The structure of compounds 2-5 were confirmed by means of ¹H NMR and ¹³C NMR spectrometry. Compound 5 (DL-threo) presents insensibility antibacterial activity.

References:

1. Korzybski T., Kowszyk-Gindifer Z., Kuryłowicz W.: in: Antybiotyki. Pochodzenie, rodzaje i właściwości, PZWL, Warszawa, 1977, str. 403-409.
2. Krajewska D., Różański A., J. Antibiotics (Tokyo) 1999, 52, 1140
3. Krajewska D., Dąbrowska M., Jakoniuk P., Różański A., Acta Pol. Pharm. 2000, 59, 127.

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