Synthesis of N,N'-diarylalkanediamides and their antimycobacterial and antialgal activity

L Kubicova,K Waisser,Z Odlerova,J Kunes,M Slosarek,K Kralova,Z Svoboda,J Janota

doi:10.3390/ecsoc-3-01766

L Kubicova, K Waisser + Show 6 more

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https://doi.org/10.3390/ecsoc-3-01766

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Abstract

A set of N,N'-diarylalkanediamides was synthesised. The compounds were tested for their antimycobacterial and antialgal activity. The antimycobacterial activity of N,N'-diarylalkanediamides depends on the lipophilicity of the respective acid. Antimycobacterially active substances were found only in the series of N,N'-diarylethanediamides and N,N'-diarylbutanediamides. Other compounds (derivatives of pentane-, hexane-, octane- and nonanediamide) were inactive against various strains of mycobacteria. The compounds inhibited growth and chlorophyll production in Chlorella vulgaris. Their relatively low antialgal activity is caused by their low aqueous solubility, and hence by a restricted passage of the inhibitor through the hydrophilic regions of thylakoid membranes.

Highlights

As the end of the 20th century witnesses a sharp rise in the incidence of mycobacterial infections, the development of new antimycobacterial drugs is presently of utmost importance and should proceed at a rapid pace
In our previous study [6] we found that N,N'-bis(3,4-dichlorophenyl)butanediamide effectively inhibited oxygen evolution rate (OER) in spinach chloroplasts and that this compound interacted with the pigment-protein complexes in photosystem 2
The decrease in biological activity with increasing lipophilicity of the compounds is probably linked to their lowered aqueous solubility, and to a restricted passage of the inhibitor through the hydrophilic regions of thylakoid membranes

Summary

Introduction

As the end of the 20th century witnesses a sharp rise in the incidence of mycobacterial infections, the development of new antimycobacterial drugs is presently of utmost importance and should proceed at a rapid pace. This study is focused on the synthesis of a large set of N,N'-diarylalkanediamides and on the study of antimycobacterial and antialgal activity of these compounds. Compounds 1-46 were tested for their in vitro antimycobacterial activity against Mycobacterium tuberculosis, M. avium, M. fortuitum, and M. kansasii.

Results

Conclusion