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Who can model new quinolone-type heterocycles as potential antibacterials?
Synthesis of thieno[2',3':4,5]thieno[3,2-b]- pyridone-3-carboxylic acids

Ulrich Jordis, Fritz Sauter and Peter Martinek

Vienna University of Technology, Inst. Organic Chemistry, Getreidemarkt 9/154, A-1060 Vienna, Austria
 ga.gif
Keywords Quinolones / Gyrase inhibitors
Invitation to molecular modelling Comparison with norfloxacine
Download the structures Click here to open the overlap.tgf file in ISIS/Draw.

Click here to see the reaction scheme.

Abstract

 The synthesis of members of a new heterocyclic ring system (thieno[2',3':4,5]thieno[3,2-b]pyridine) is described. Compound 9 (and fluorinated derivatives thereof) seem to have a similar spatial arrangement of functional groups as the "mother" of third generation quinolones, norfloxacine. Readers might have the resources and expertise to compare the two structures.
Accompanying poster

Explanation and invitation for discussion

In continuation of works described in the accompanying paper [1]Benzothieno[3,2-b]pyridone-3-carboxylic acids as potential antibacterials the title compounds were synthesized using the same methodology.

Compound 9 - not containing the fluorine atom depicted in the above comparison with Norfloxacin - showed no antibacterial activity to warrant further development, but calculations might justify the effort to place a fluorine atom at the desired position of the molecule.

Synthesis

The synthetic sequence is described in Scheme 1. Click here to spawn ISIS/Draw to view the file.

You can also view the scheme here as a jpeg