Synthesis, characterization and antimicrobial activity evaluation of new imidazo [2,1-b][1,3,4]thiadiazole derivatives

Alegaon, Shankar G.; Alagawadi, K. R.

doi:10.5155/eurjchem.2.1.94-99.161

Cited by 28 publications

(20 citation statements)

References 30 publications

(39 reference statements)

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“…These heterocyclic systems, in which imidazole and 1,3,4‐thiadiazole rings are fused to each other with a bridgehead nitrogen atom, are referred to as imidazo[2,1‐ b ][1,3,4]thiadiazoles . Imidazo[2,1‐ b ][1,3,4]thiadiazoles and their derivatives are widely used in medicine, pharmaceutics, and pharmaceutical chemistry because of their numerous biological activities, including antimicrobial , antifungal , antibacterial , anti‐inflammatory, antitubercular , analgesic , and diuretic activities.…”

Section: Introductionmentioning

confidence: 99%

Novel Substituted Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives: Synthesis, Characterization, Molecular Docking Study, and Investigation of Their In Vitro Antifungal Activities

Tahtacı

Karakurt

et al. 2019

Journal of Heterocyclic Chem

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In this study, a new series of substituted imidazo[2,1‐b][1,3,4]thiadiazole derivatives were synthesized. To this end, first 2‐amino‐1,3,4‐thiadiazole derivatives (compounds 2a and 2b), the starting materials, were synthesized with high yields (82% and 79%, respectively). Then imidazo[2,1‐b][1,3,4]thiadiazole derivatives (4–16), the target compounds, were synthesized from reactions of 2‐amino‐1,3,4‐thiadiazole derivatives (2a and 2b) with 2‐bromoacetophenone derivatives (3a–3i) (in yields of 52% to 71%). All of the synthesized compounds were characterized by 1H NMR, 13C NMR, Fourier transform infrared, elemental analysis, mass spectroscopy, and X‐ray diffraction analysis (compounds 4–12, 14, and 15) techniques. In vitro antifungal activity tests were performed for all of the synthesized compounds. Inhibition zones, percentage of inhibition, minimum fungicidal activity, minimum inhibitory concentration, and lethal dose values of the target compounds were determined against some plant pathogens. According to the results of the biological activity tests, all of the synthesized compounds showed moderate to high levels of antifungal activity. Theoretical calculations were performed to support the experimental results. The geometric parameters of selected compounds (5, 6, and 8) were optimized using the density functional theory B3LYP/6‐31G(d) method in the Gaussian 09W package program, and the frontier molecular orbitals (highest occupied molecular orbital–lowest unoccupied molecular orbital) were calculated theoretically. Finally, molecular docking studies were performed for antifungal activity studies of the selected compounds and to determine whether or not these compounds could be inhibitor agents for the 2RKV protein structure.

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Section: Introductionmentioning

confidence: 99%

Novel Substituted Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives: Synthesis, Characterization, Molecular Docking Study, and Investigation of Their In Vitro Antifungal Activities

Tahtacı

Karakurt

et al. 2019

Journal of Heterocyclic Chem

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“…Owing to the fact that imidazo[2,1‐ b ][1,3,4]thiadiazoles and their derivatives exhibit many biological activities such as antimicrobial,, antifungal, antibacterial, anti‐inflammatory, antituberculosis, analgesic, diuretic activities, the synthesis of these compounds and their derivatives increases gradually ,…”

Section: Introductionmentioning

confidence: 99%

“…[7][8][9] These heterocyclic systems where the imidazole and 1,3,4-thiadiazole rings are fused with a bridgehead nitrogen atom are known as imidazo[2,1-b] [1,3,4]thiadiazoles. [10][11][12] Owing to the fact that imidazo[2,1-b] [1,3,4]thiadiazoles and their derivatives exhibit many biological activities such as antimicrobial, [13,14] antifungal, [15] antibacterial, [16][17][18] antiinflammatory, [19][20][21] antituberculosis, [22][23][24][25] analgesic, [26] diuretic [27] activities, the synthesis of these compounds and their derivatives increases gradually. [28,29] Besides being used as an anthelmintic drug, the fact that these compounds are bio-isostere of Tetramisole and its enantiomers Levamisole and Dexamisole [30,31] that are used as regulating and strengthening elements for immune system, has caused the anti-cancer activity studies to focus on imidazo [2,1-b] [1,3,4]thiadiazole derivatives.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, SAR and Molecular Modeling Studies of Novel Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives as Highly Potent Antimicrobial Agents

Tahtacı

Karacık

Ece

et al. 2017

Molecular Informatics

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In this study, a novel series of phenyl substituted imidazo[2,1-b][1,3,4]thiadiazole derivatives were synthesized, characterized and explored for antibacterial activity against Gram-negative Escherichia coli, Gram-positive Staphylococcus aureus and Bacillus subtilis and antifungal activity against Candida albicans. Most of the synthesized compounds exhibited remarkable antimicrobial activities, some of which being ten times more potent than positive controls. The most promising compound showed excellent activity with MIC value of 0.03 μg/ml against both S. aureus and B. subtilis (MIC values of positive compound Chloramphenicol are 0.4 μg/ml and 0.85 μg/ml, respectively). Furthermore, structure-activity relationship was also investigated with the help of computational tools. Some physicochemical and ADME properties of the compounds were calculated too. The combination of electronic structure calculations performed at PM6 level and molecular docking simulations using Glide extra-precision mode showed that the hydrophobic nature of keto aryl ring with no electron withdrawing substituents at para position enhances activity while electron-donating substituents at the second aryl ring is detrimental to activity.

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“…Alegaon and Alagawadi [44] reported the synthesis of hybrid molecules of imidazo [1,3,4]thiadiazoles and N-carboxymethyl rhodanine and the subsequent evaluation of their antibacterial activities. Compound 5 is representative of this series and showed significant activity against S. aureus (MIC=4 µg/mL), as well as moderate activity against E. coli (MIC=32 µg/mL) ( Figure 5).…”

Section: Naohmentioning

confidence: 99%

The Synthesis and Anti-Bacterial Activities of N-carboxymethyl Rhodanines

Piao¹

2014

Med chem

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A large number of reports have been published in recent years regarding the use of N-carboxymethyl rhodanines as antimicrobial agents. Molecules belonging to this structural class have been reported to exhibit good inhibitory activities towards various Gram-positive bacteria, including several multidrug-resistant strains such as methicillinresistant Staphylococcus aureus and quinolone-resistant Staphylococcus aureus. In this mini-review, we have provided a summary of recent research directed towards the synthesis of N-carboxymethyl rhodanines, and their pharmacological evaluation as antimicrobial agents.

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Synthesis, characterization and antimicrobial activity evaluation of new imidazo [2,1-b][1,3,4]thiadiazole derivatives

Cited by 28 publications

References 30 publications

Novel Substituted Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives: Synthesis, Characterization, Molecular Docking Study, and Investigation of Their In Vitro Antifungal Activities

Novel Substituted Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives: Synthesis, Characterization, Molecular Docking Study, and Investigation of Their In Vitro Antifungal Activities

Design, Synthesis, SAR and Molecular Modeling Studies of Novel Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives as Highly Potent Antimicrobial Agents

The Synthesis and Anti-Bacterial Activities of N-carboxymethyl Rhodanines

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