Novel imidazo[2,1-b][1,3,4]thiadiazole (ITD) hybrid compounds: Design, synthesis, efficient antibacterial activity and antioxidant effects

Taflan, Ebru; Bayrak, Hacer; Er, Mehtap; Karaoğlu, Şengül Alpay; Bozdeveci, Arif

doi:10.1016/j.bioorg.2019.102998

Cited by 24 publications

(15 citation statements)

References 26 publications

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“…1,3,4-Thiadiazole derivatives have shown extensive biological activities, such as antiinflammatory (Maddila et al, 2016), anticancer (Yang et al, 2012;Sridhar et al, 2020), antifungal (Alwan et al, 2015;Bhinge et al, 2015;Chudzik et al, 2019), antibacterial (Aggarwal et al, 2012;Taflan et al, 2019;Zhang et al, 2019), and plant growth regulator (Knyazyan et al, 2012) activities. Since 1,3,4-thiadiazole compounds with antibacterial activity was synthesized by Masaki in the 1950s, 1,3,4-thiadiazole pesticides, such as Bismerthiazol and Thiodiazole-copper, have been developed and widely used in agriculture.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Bioactivities of Novel 1,3,4-Thiadiazole Derivatives of Glucosides

Chen

Zhang

et al. 2021

Front. Chem.

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A series of novel 1,3,4-thiadiazole derivatives of glucosides were synthesized by the starting materials d-glucose and 5-amino-1,3,4-thiadiazole-2-thiol in good yields with employing a convergent synthetic route. The results of bioactivities showed that some of the target compounds exhibited good antifungal activities. Especially, compounds 4i showed higher bioactivities against Phytophthora infestans (P. infestans), with the EC50 values of 3.43, than that of Dimethomorph (5.52 μg/ml). In addition, the target compounds exhibited moderate to poor antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas campestris pv. citri (Xcc).

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Section: Introductionmentioning

confidence: 99%

Synthesis and Bioactivities of Novel 1,3,4-Thiadiazole Derivatives of Glucosides

Chen

Zhang

et al. 2021

Front. Chem.

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“…[14][15][16] These fused heterocyclic compounds and their derivatives have become widely used compounds in pharmaceutical chemistry due to their wide variety of biological activities, such as antifungal, antibacterial, antimicrobial, antioxidant, anticonvulsant, antiviral, antidepressant, antiinflammatory, antihypertensive, antituberculosis, and antiproliferative activities. [10,[17][18][19][20][21][22][23][24][25][26][27][28][29] Moreover, the synthesis of these compounds and their derivatives has also become a commonly investigated topic in anticancer activity studies due to their structures being similar those of Levamisole, Tetramisole, and Dexamisole, which are good immune system regulators and enhancers. [30,31] In light of the important literature data mentioned above, this study focused on the synthesis of thioetherbridged 2,6-disubstituted imidazo [2,1-b] [1,3,4]thiadiazole derivatives, their characterization by various spectroscopic methods, and an investigation of their antifungal activity against various plant pathogens.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structural characterization, biological activity, and theoretical studies of some novel thioether‐bridged 2,6‐disubstituted imidazothiadiazole analogues

Tunel

Alıcı

et al. 2021

Journal of Heterocyclic Chem

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In this study, thioether-bridged imidazo [2,1-b][1,3,4]thiadiazole derivatives that contained both imidazole and 1,3,4-thiadiazole (compounds 7a-7i and 8a-8i) were synthesized from the reactions of 2-amino-1,3,4-thiadiazole with phenacyl bromide (6a-6i) (at yields of 59% to 74%). The structure of the synthesized compounds was characterized using 1 H NMR, 13 C NMR, Fouriertransform infrared spectroscopy, elemental analysis, mass spectroscopy, and Xray diffraction analysis. Mycelial growth, mycelial growth inhibition, minimum inhibitory concentration, minimum fungicidal concentration, and lethal dose values against various plant pathogenic fungi were determined for all of the target compounds synthesized in the study. The test results showed that most of the compounds had moderate to good antifungal activity. In addition, the absorption, distribution, metabolism, excretion (ADME) parameters of the compounds were calculated, and it was observed that all of the compounds met the drug-likeness rules in general. Finally, using docking simulations, it was found that compounds 7h, 7i, 8h, and 8i showed high affinity to PDB ID:5TZ1, which is an CYP51 antifungal target structure.

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“…found that imidazo[2,1‐ b ]‐1,3,4‐thiadiazoles ( 6 ) displayed substantial antifungal activity with MICs between 1.56 and 100 μg/mL against Candidia albicans , Cryptococcus neoformans , and Aspergillus niger . Taflan et al [33] . found that some imidazo[2,1‐ b ][1,3,4]thiadiazole hybrid compounds ( 7 ) showed broad‐spectrum antimicrobial activity with MIC values between 0.24 and 3.9 μg/mL.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity Evaluation of Imidazole‐Fused Imidazo[2,1‐b][1,3,4]thiadiazole Analogues

et al. 2021

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Three series of new imidazole‐fused imidazo[2,1‐b][1,3,4]thiadiazole analogues (compounds 20 a–g, 21 a–g, and 22 a–g) have been synthesized, and their antibacterial and antifungal activities have been evaluated. All the target compounds showed strong antifungal activity and high selectivity for the test fungus Candida albicans over Gram‐positive and ‐negative bacteria. N‐((4‐(2‐Cyclopropyl‐6‐(4‐fluorophenyl)imidazo[2,1‐b][1,3,4]thiadiazol‐5‐yl)‐5‐(6‐methyl‐pyridin‐2‐yl)‐1H‐imidazol‐2‐yl)methyl)aniline (21 a) showed the highest activity against C. albicans (MIC50=0.16 μg/mL), 13 and three times that of the positive control compounds gatifloxacin and fluconazole, respectively. Compounds 21 a and 20 e did not show cytotoxicity against human foreskin fibroblast‐1 cells, and compound 21 a was as safe as the positive control compounds in hemolysis tests. These results strongly suggest that some of the compounds produced in this work have value for development as antifungal agents.

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Novel imidazo[2,1-b][1,3,4]thiadiazole (ITD) hybrid compounds: Design, synthesis, efficient antibacterial activity and antioxidant effects

Cited by 24 publications

References 26 publications

Synthesis and Bioactivities of Novel 1,3,4-Thiadiazole Derivatives of Glucosides

Synthesis and Bioactivities of Novel 1,3,4-Thiadiazole Derivatives of Glucosides

Synthesis, structural characterization, biological activity, and theoretical studies of some novel thioether‐bridged 2,6‐disubstituted imidazothiadiazole analogues

Synthesis and Antimicrobial Activity Evaluation of Imidazole‐Fused Imidazo[2,1‐b][1,3,4]thiadiazole Analogues

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