Amidrazones - hydrazones of acid amides have been shown to be important precursors or intermediates to obtain various compounds with industrial aplications. Moreover NCNN group is an essential part of molecules bearing high biological activities and it is template in drug discovery. Open-chain or cyclic derivatives of the amidrazones and also their metal complexes are known to exhibit following activities: antithrombotic, antiinflamatory, antibacterial, antimalarial, antifungal, anticancer and insulin-mimetic.

The subject of our present study was biological activity of hexahydro-1H-isoindole-1,3(2H)-diones (1-3) and 2-cyclohexanecarboxylic acid derivatives (4, 5). Products were obtained in the reaction of some N³-substituted amidrazones with cis-1,2-cyclohexanedicarboxylic anhydride [1,2].

1 R₁=2-C₅H₄N, R₂=C₆H₅; 4 R₁=2-C₅H₄N, R₂=4-NO₂-C₆H₄;

2 R₁=C₆H₅, R₂=4-NO₂-C₆H₄ 5 R₁=2-C₅H₄N, R₂=2-C₅H₄N;

3 R₁=C₆H₅, R₂=C₆H₅;

The chemical structure of compounds was confirmed by IR, ¹H NMR, EI-MS, elemental analysis and X-ray crystallography. Their purity was confirmed by chromatographic methods.

The products (1-5) were tested in vitro against bacterial and fungal species. MIC₅₀ values were determined as the lowest concentration of compound which inhibited 50% of growth of the microorganism tested. The sensitivities to the derivatives 1, 4, and 5 were similar (MIC₅₀ 100-250 mg/ml) for the following strains: Nocardia spp., Enterococcus faecalis ATCC 29212, Sarcina lutea, and Yersinia enterocolitica O3. Product 1, MIC₅₀ 250 mg/ml, was also active against Staphylococcus aureus ATCC 25923. Compound 3 was shown to be effective against the Gram-positive bacteria Staphylococcus aureus ATCC 25923, Sarcina lutea and Enterococcus faecalis ATCC 29212 as well as against the fungi Aspergillus niger and Candida albicans at a concentration of 250 mg/ml [2]. Derivative 2 exhibited a relatively high antibacterial potency against Sarcina lutea (MIC₅₀ 75 mg/ml), Pseudomonas aeruginosa ATCC 27853 and Yersinia enterocolitica O3 (MIC₅₀ 200 mg/ml). The examined compounds did not inhibit the growth of the fast growing Mycobacterium smegmatis or strains used as drug resistant markers, Escherichia coli ATCC 25922 and Pseudomonas aeruginosa ATCC 27853 (except derivative 2).

References:
[1] Modzelewska-Banachiewicz, B.; Rzeski, W.; Nowaczyk A.; Ucherek, M. Acta Pol Pharm - Drug Research, 62, 5 (2006)
[2] Modzelewska-Banachiewicz, B., Kutkowska J., Ucherek, M., XX Naukowy Zjazd PTFarm, Poster No. S.14.P-9

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