Theoretical and synthetic approach towards the biology of some novel monobactam induced sulphonamides : assessing biology through coupling of active ingredients

Abstract EN

Novel monobactams were designed and synthesized by coupling the monocyclic azetidinones with sulphapyridine moiety in order to assess the possibility to enhance the bactericidal activity through a synergistic dual-action mechanism.

In a process, sulphapyridine (4) was condensed with different aromatic aldehydes to obtain anils 5 (a-h) which on Staudinger [2 + 2] cycloaddition with chloroacetyl chloride produced N-sulphapyridinyl-3-chloro-4- (substituted) azetidin-2-ones 6(a-h).

Their structures were confirmed by 1H-NMR, IR, Mass spectra and elemental analysis.

The activities were tested, in vitro, against a panel of selected bacteria.

A correlation of structure and activities relationship of these compounds with respect to molecular modeling, Lipinski rule of five, drug likeness, toxicity profiles and other physicochemical properties of drugs are described and verified experimentally.