Synthetic Transition from Thiourea-Based Compounds to Tetrazole Derivatives: Structure and Biological Evaluation of Synthesized New N-(Furan-2-ylmethyl)-1H-tetrazol-5-amine Derivatives

Abstract

Twelve novel derivatives of N-(furan-2-ylmethyl)-1H-tetrazol-5-amine were synthesized. For obtained compound 8, its corresponding substrate single crystals were isolated and X-ray diffraction experiments were completed. In the initial stage of research, in silico structure-based pharmacological prediction was conducted. All compounds were screened for their antibacterial and antimycobacterial activities using standard and clinical strains. The cytotoxic activity was evaluated against a panel of human cancer cell lines, in contrast to normal (HaCaT) cell lines, by using the MTT method. All examined derivatives were found to be noncytotoxic against normal cell lines. Within the studied group, compound 6 showed the most promising results in antimicrobial studies. It inhibited four hospital S. epidermidis rods’ growth, when applied at the amount of 4 µg/mL. However, the most susceptible to the presence of compound 6 was S. epidermidis T 5501 851/19 clinical strain, for which the MIC value was only 2 µg/mL. Finally, a pharmacophore model was established based on lead compounds from this and our previous work.

Novel Tetrazole-Based Antimicrobial Agents Targeting Clinical Bacteria Strains: Exploring the Inhibition of Staphylococcus aureus DNA Topoisomerase IV and Gyrase

“…The transition presented here from imide-thiourea substrates, thoroughly studied in our previous works [ 22 , 23 , 24 , 25 ], to appropriate novel imide-tetrazole products was successfully performed in the course of a single reaction. All synthesized compounds were tested in vitro against a set of bacteria, including representative standard Gram-positive and Gram-negative rods.…”

“…In previous years, our research group was devoted to searching for new tetrazole-based compounds with antimicrobial activity [ 22 , 23 , 24 , 25 ]. Clinicians use the tetrazole-derived antimicrobial drugs such as Cefamandole, Ceftezole, both second-generation broad-spectrum cephalosporin antibiotics, and the oxazolidinone-class antibiotic Tadalizolid.…”

“…Thiourea derivatives of two imides with confirmed antimicrobial activity were used as substrates for the synthesis of tetrazole-imide hybrids [ 29 , 30 ]. Our previous studies showed that the introduction of tetrazole arrangement in thiourea derivatives leads to an increase of antimicrobial activity [ 22 , 23 , 24 , 25 ].…”

Construction of biomass-based amines via Ir-mediated N-alkylation: kinetic analysis

“…12 Secondary amines are important in the fields of pharmaceuticals, medicinal chemistry, corrosion inhibitors of carbon steel, and extractants of rare-earth elements and noble metals. [15][16][17][18][19][20][21][22] Thus, various secondary amines were developed herein employing the catalytic N-alkylation of biomass-based primary amines with biomass-based primary alcohols under environmentally friendly conditions. Typically, N-alkylation of tetrahydrofurfurylamine (1a, amine) using furfuryl alcohol (2a, alcohol) as an alkylating agent was investigated for the synthesis of 1-(2furanyl)-N-[(2-tetrahydrofuranyl)methyl]methanamine (5a, secondary amine) in this research study (Scheme 1c).…”

Design and Synthesis of Menthol and Thymol Derived Ciprofloxacin: Influence of Structural Modifications on the Antibacterial Activity and Anticancer Properties

“…Encouraged by published results related to Ciprofloxacin-monoterpenes hybrids and our experience in research for new antimicrobial agents [ 29 , 30 , 31 , 32 , 33 ], we have decided to design and synthesize series of Ciprofloxacin derivatives with the utilization of menthol and thymol scaffolds. Furthermore, we wanted to explore the impact on antimicrobial activity, cytotoxicity and some of the physicochemical properties of novel compounds versus reference Ciprofloxacin.…”