Abstract
A series of 2-(1H-indol-3-yl)ethylthiourea derivatives were prepared by condensation of 2-(1H-indol-3-yl)ethanamine with appropriate aryl/alkylisothiocyanates in anhydrous media. The structures of the newly synthesized compounds were confirmed by spectroscopic analysis and the molecular structures of 8 and 28 were confirmed by X-ray crystallography. All obtained compounds were tested for antimicrobial activity against Gram-positive cocci, Gram-negative rods and for antifungal activity. Microbiological evaluation was carried out over 20 standard strains and 30 hospital strains. Compound 6 showed significant inhibition against Gram-positive cocci and had inhibitory effect on the S. aureus topoisomerase IV decatenation activity and S. aureus DNA gyrase supercoiling activity. Compounds were tested for cytotoxicity and antiviral activity against a large panel of DNA and RNA viruses, including HIV-1 and other several important human pathogens. Interestingly, derivative 8 showed potent activity against HIV-1 wild type and variants bearing clinically relevant mutations. Newly synthesized tryptamine derivatives showed also a wide spectrum activity, proving to be active against positive- and negative-sense RNA viruses.
Highlights
Indole derivatives have attracted a great deal of attention due to their wide therapeutic applications (Figure 1)
The antibacterial activity of compounds was tested against a series of Gram-positive bacteria: Staphylococcus aureus ATCC 4163, Staphylococcus aureus ATCC 25923, Staphylococcus aureus ATCC
Antimicrobial activity was examined by the disc diffusion and Minimal Inhibitory Concentration (MIC) method under standard conditions, using Mueller–Hinton II agar medium (Becton Dickinson, Franklin Lakes, NJ, USA) for bacteria and RPMI agar with 2% glucose
Summary
Indole derivatives have attracted a great deal of attention due to their wide therapeutic applications (Figure 1). The cytotoxic [13,14,15,16] and anticancer potency of substituted indole compounds was proven In this field they act as inhibitors of serine/threonine kinase (AKT) [17], tyrosinase [18], human sirtuins SIRT1-3 [19] or transcription factors NF-kB activation [20]. The thiourea moiety is an important synthon responsible for numerous biological activities, such as antimicrobial [21,22,23] antiviral [24,25], antiproliferative [26] and cytotoxic effects [22,27]. Through rationally planned modifications of thiourea derivative structures, a wide range of compounds with high pharmacological activity and low side-effects can be obtained. In turn, increases the bioavailability of the compound, which improves its pharmacokinetic parameters
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