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Fifteen novel aryl, substituted aryl and heteroaryl γ-hydroxy- (2a-e), γ-methoxyimino- (3a-e), and γ-benzyloxyimino- (4a-e) butyric acid methyl esters were investigated for their enzyme inhibition, and the synthesis of 10 compounds (3a-e, 4a-e) is given in this study. The other five compounds (2a-e) were synthesized before in another study. Compounds 3a-e and 4a-e were synthesized in this work as original compounds and characterized by H and C NMR, IR, mass, and elemental analyses. Their (E/Z)-isomerisation ratios were analyzed by H and C NMR. All of them are of pure (E)-configuration. Due to the literature survey, the elastase inhibition activity was not studied for these compounds. Elastase inhibition ability was investigated in this work for five γ-hydroxy- (2a-e), five γ-methoxy- (3a-e), and five γ-benzyloxyimino- (4a-e) butyric acid methyl esters. All these 15 compounds showed elastase inhibition activity. Compound 2b was the best one and exhibited a better activity than the standard ursolic acid whereas compound 2a worked like the standard. All these compounds can be novel elastase inhibitor agents in the pharmaceutical and cosmetic industries.

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All reagents were obtained from commercial suppliers unless otherwise stated. Organic solvents were routinely dried and/or distilled prior to use and stored over molecular sieves under argon. Solvents for chromatography were technical grade and distilled prior to use. Thin layer chromatography (TLC) was carried out on Merck aluminium support plates Silica gel 60 F254.Visualization was achieved under a UV mineral light. Column chromatography was performed using silica gel Merck 60 (particle size 0.2-0.063 mm). NMR spectra were recorded at 500 MHz for 1 H and at 125 MHz for 13 C using Me4Si as the internal standard in CD3OD, and CDCl3. GC-MS were recorded on Shimadzu/QP2010 Plus. IR spectra were recorded on Mattson 1000. Melting points were determined with Buchi melting point B-540. Chemical yields refer to pure isolated substances.

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