Synthesis and Biological Evaluation of Novel Indole-Derived Thioureas

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.

Chromene- and Quinoline-3-Carbaldehydes: Useful Intermediates in the Synthesis of Heterocyclic Scaffolds

“…Antitumoral [ 21 , 22 ], anti-arrhythmic [ 19 ], anti-inflammatory [ 23 ], antimicrobial [ 24 ], and antihypertensive properties are amongst the reported biological activities. The synthesis of indole derivatives is largely explored due to relevant biological applications described for this scaffold, and there are reports on the synthesis of indole hybrids [ 25 , 26 , 27 ]. We thought it would be interesting to obtain chromene-indole hybrids, so we studied the reaction of 2-aryl-4-chloro-2 H -chromene-3-carbaldehydes 2a – c with indole ( 3 ).…”

G protein‐coupled receptor binding and pharmacological evaluation of indole‐derived thiourea compounds

“…The synthesis of thiourea derivatives 1 and 3 was described previously . The molecular structure of 3 has been determined.…”

Untitled

“…SAR studies reported the importance of 4bromophenyl moiety. All the compounds, (38) (EC 50 = 8.7 ± 0.4 μM) was found to be highly potent as compared to standard drug efavirenz (EC 50 = 0.002 ± 0.0002 μM) 114 . In 2016, Doussan et al, reported synthesis and evaluation of various indole derivatives for anti-HIV activity.…”

“…Sanna and his colleagues mentioned the synthesis of indolethiourea hybrids and evaluated it against a pool of microbes containing both Gram-positive and Gramnegative types. Compound (1) (minimum inhibitory concentration as MIC (minimum inhibitory concentration) < 12.5 μg/mL) was establish to be extremely potent as compared with standard drug ciprofloxacin (MIC < 1.0 μg/mL) 53 .…”