Synthesis, antibacterial and QSAR evaluation of 5-oxo and 5-thio derivatives of 1,4-disubstituted tetrazoles

Morjan, Rami Y.; Al-Attar, Nisreen H.; Abu-Teim, Omar S.; Maschke, Ulrich; Awadallah, Adel Μ.; Mkadmh, Ahmed M.; Elmanama, Abdelraouf A.; Raftery, James; Abu-Awwad, Fakhr M.; Yaseen, Zyad J.; Elqidrea, Ammar F.; Gardiner, John M.

doi:10.1016/j.bmcl.2015.04.070

Cited by 22 publications

(12 citation statements)

References 44 publications

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“…In presence of the catalyst, the best optimised results were obtained in 6 h compared to 12 h (Table 2.2,entry 6). Among various solvents evaluated in the reaction, DMSO (Table 2, entry 1) was found to be superior to DMF ( [17][18][19][20]. Furthermore, the regioselectivity of our reaction can be rationalised through the possible steric environment around the metal centre.…”

Section: Resultsmentioning

confidence: 88%

Preparation of 2,5‐Disubstituted Tetrazoles using a Copper‐Catalysed Regioselective Direct Coupling of Tetrazoles with Free NH Groups and Boronic Acid Derivatives

Kataky,

Sarma,

Thakur

2023

ChemistrySelect

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The development of a mild and efficient protocol that allows the direct C−N coupling of N−H free tetrazole and low toxic boronic acid was presented. A careful optimization of the reaction conditions revealed that reaction proceeded smoothly in presence of a 10 mol % copper complex catalytic system without the need of any additives. Thus, the results presented herein represents a reliable and efficient protocol for the synthesis of regioselective 2,5‐disubstituted tetrazoles.

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Section: Resultsmentioning

confidence: 88%

Preparation of 2,5‐Disubstituted Tetrazoles using a Copper‐Catalysed Regioselective Direct Coupling of Tetrazoles with Free NH Groups and Boronic Acid Derivatives

Kataky,

Sarma,

Thakur

2023

ChemistrySelect

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“…In fact, all strains were inhibited at a concentration of 1.25 mg/ml, except E. coli strain which was found to be less sensitive to the tetrazolic derivative with a MIC of around 2.5 mg/ml (Table VI). It should be noted that the work of Morjan et al [30] have shown that 5-oxo and 5-thio-tetrazoles 1,4-disubstitute derivatives inhibit the growth of isolated strains in the hospital environment; S.aureus and E.coli with a MIC of 0.2 mg/ml and 0.6 mg/ml respectively.…”

Section: Minimum Inhibitory Concentrations Against Strains Of Hospita...mentioning

confidence: 99%

“…To our knowledge, there is not much work already done on the antimicrobial activity of tetrazole derivatives on strains of hospital origin except a study by Morjan et al [30] on 5-oxo and 5-thiotetrazoles 1,4-disubstituted derivatives. The results of this study show that some 5-oxo-tetrazole derivatives have activities on E. coli, Streptococcus spp and S. aureus with halos of inhibition of 5 mm, 5-6 mm and 6 mm respectively.…”

Section: Identification Of Antibacterial Activity Against Strains Of ...mentioning

confidence: 99%

Evaluation of the Antibacterial Activity of 5-(thiophen-2-yl)-1H-tetrazole and Its Oxime Derivative against ATCC Reference Strains and Strains Isolated from the Hospital Environment of a Provincial Public Hospital in the City of Fez

Hajib

Hssaini

Alami

et al. 2021

EJCHEM

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Bacterial resistance to antibiotics and disinfectants has become a real concern. The hospital presents a favorable environment for the colonization and development of bacteria resistant to antibiotics and disinfectants. The search for new antimicrobial compounds is essential to combat this phenomenon. Tetrazole derivatives may represent a solution due to their interesting antibacterial activity. In this work, two tetrazole derivatives; thiophene-2-carbaldehyde (T2C) and 5-(thiophen-2-yl)-1H-tetrazole (5TPh-1HT), were evaluated for their antibacterial activities against a set of reference strains and strains isolated from the hospital environment. The antibacterial effect was studied by the disc diffusion method and by determination of MIC and MBC. The 5-(thiophen-2-yl)-1H-tetrazole (5TPh-1HT) has a broader spectrum of activity than its oxime derivative (T2C). The latter has bactericidal activity only on gram-negative Escherichia coli, Pseudomonas aeruginosa with MICs ranging from 0.62 mg/ml to 2.5 mg/ml, while 5TPh-1HT has a bactericidal effect on all strains with MICs ranging from 0.62 mg/ml to 1.25 mg/ml. Both products have a significant inhibitory activity on the strains tested in particular E. coli H, S. aureus H, P. aeruginosa and Streptococcus spp A. It was found that these activities vary depending on the microbial strain tested and the product applied.

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“…Although many QSAR models for describing and predicting the antibacterial activity of small-molecule compounds have been published to date, they are mostly focused on an individual class of compounds or on a pre-defined scaffold (Morjan et al, 2015; Leemans et al, 2016). As a rule, such models are not applicable for diverse compound libraries at all, because input parameters, for example, molecular descriptors, are mainly selected to properly describe the chemical space around a chemotype studied.…”

Section: Introductionmentioning

confidence: 99%

Identification of Novel Antibacterials Using Machine Learning Techniques

et al. 2019

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Many pharmaceutical companies are avoiding the development of novel antibacterials due to a range of rational reasons and the high risk of failure. However, there is an urgent need for novel antibiotics especially against resistant bacterial strains. Available in silico models suffer from many drawbacks and, therefore, are not applicable for scoring novel molecules with high structural diversity by their antibacterial potency. Considering this, the overall aim of this study was to develop an efficient in silico model able to find compounds that have plenty of chances to exhibit antibacterial activity. Based on a proprietary screening campaign, we have accumulated a representative dataset of more than 140,000 molecules with antibacterial activity against Escherichia coli assessed in the same assay and under the same conditions. This intriguing set has no analogue in the scientific literature. We applied six in silico techniques to mine these data. For external validation, we used 5,000 compounds with low similarity towards training samples. The antibacterial activity of the selected molecules against E. coli was assessed using a comprehensive biological study. Kohonen-based nonlinear mapping was used for the first time and provided the best predictive power (av. 75.5%). Several compounds showed an outstanding antibacterial potency and were identified as translation machinery inhibitors in vitro and in vivo . For the best compounds, MIC and CC 50 values were determined to allow us to estimate a selectivity index (SI). Many active compounds have a robust IP position.

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Synthesis, antibacterial and QSAR evaluation of 5-oxo and 5-thio derivatives of 1,4-disubstituted tetrazoles

Cited by 22 publications

References 44 publications

Preparation of 2,5‐Disubstituted Tetrazoles using a Copper‐Catalysed Regioselective Direct Coupling of Tetrazoles with Free NH Groups and Boronic Acid Derivatives

Preparation of 2,5‐Disubstituted Tetrazoles using a Copper‐Catalysed Regioselective Direct Coupling of Tetrazoles with Free NH Groups and Boronic Acid Derivatives

Evaluation of the Antibacterial Activity of 5-(thiophen-2-yl)-1H-tetrazole and Its Oxime Derivative against ATCC Reference Strains and Strains Isolated from the Hospital Environment of a Provincial Public Hospital in the City of Fez

Identification of Novel Antibacterials Using Machine Learning Techniques

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