Novel substituted benzothiazole and Imidazo[2,1-b][1,3,4]Thiadiazole derivatives: Synthesis, characterization, molecular docking study, and investigation of their in vitro antileishmanial and antibacterial activities

Er, Mustafa; Özer, Arif; Direkel, Şahin; Karakurt, Tuncay; Tahtacı, Hakan

doi:10.1016/j.molstruc.2019.05.104

Cited by 41 publications

(29 citation statements)

References 29 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compounds 3 and 9 were obtained from the reactions of 5-amino-1,3,4-thiadiazole-2-thiol (2) with 2,4dichlorobenzylchloride (1) and 4-fluorobenzylchloride (8) in the presence of KOH with high yields (88 % and 89 %), as indicated in the literature. [34][35][36] The other starting compound, compound 15, was synthesized from the reaction of nitrile compound (14) with thiosemicarbazide in trifluoroacetic acid (TFA) at 60°C with a high yield (88 %). [37] In this reaction, the nucleophilic attack of thiosemicarbazide to the imine carbon occurs first under the catalytic effect of TFA.…”

Section: Chemistrymentioning

confidence: 99%

Synthesis, Characterization, Antimicrobial Evaluation, and Computational Investigation of Substituted Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives

Dagli

Karakurt

et al. 2020

ChemistrySelect

Self Cite

View full text Add to dashboard Cite

In this study, a novel series of 2,6-disubstituted and 2,5,6trisubstituted imidazo[2,1-b][1,3,4]thiadiazole derivatives were synthesized starting from 2-amino-1,3,4-thiadiazole derivatives. Structures of the synthesized compounds were characterized using various analysis techniques. Then, in vitro biological activity tests were carried out for all synthesized compounds and they were found to show moderate to good activity against all bacteria and fungi tested. Next, molecular docking simulations were performed to observe the inhibition effect of the synthesized compounds on the 3R9C receptor and support their biological activity results. Finally, the pharmacokinetic, ADME and toxicity properties of all compounds were examined using FAF-Drugs and ProTox webservers and it was concluded that they had acceptable toxicity and ADME properties.

show abstract

Section: Chemistrymentioning

confidence: 99%

Synthesis, Characterization, Antimicrobial Evaluation, and Computational Investigation of Substituted Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives

Dagli

Karakurt

et al. 2020

ChemistrySelect

Self Cite

View full text Add to dashboard Cite

show abstract

“…Benzothiazole compounds display a broad-spectrum biological activity [5,6,8,11,14,17,[20][21][22][23][24]. Thus, they usually act as an important guide frame and parent skeleton, which plays very important roles in medicinal chemistry and agrochemicals.…”

Section: Discussionmentioning

confidence: 99%

“…Thus, they usually act as an important guide frame and parent skeleton, which plays very important roles in medicinal chemistry and agrochemicals. However, to the best of our knowledge, few reports on antimicrobial activity of benzothiazole derivatives against pathogenic fungi and bacteria have been published [14,18,23]. Benzothiazole-based antibacterial compounds bind to different biological targets in bacterial cells and have been shown to be inhibitors of enzymes that are important for essential processes in the bacterial cells such as cell wall synthesis, cell division, and DNA replication, or biosynthesis of essential compounds [22,25,26].…”

Section: Discussionmentioning

confidence: 99%

“…E. coli dihydroorotase has been described as a molecular target for benzothiazoles [23]. Computational and molecular modeling studies were carried out to explain the molecular basis underlying the interaction of benzothiazole derivatives with E. coli dihydroorotase.…”

Section: Computational Studiesmentioning

confidence: 99%

“…In addition, the potential antimicrobial activity of benzothiazole derivatives was previously illustrated [13][14][15][16][17]. The results of these studies concluded that the antimicrobial activity of benzothiazole derivatives can be attributed to its ability to interact with several cellular targets including Staphylococcus (S.) aureus DNA gyrase [18][19][20], Escherichia (E.) coli dihydropteroate synthase [21], Plasmodium dihydrofolate reductase [22], and, recently, E. coli dihydroorotase [23]. Thus, the aim of the current study was to test the antimicrobial potential of benzothiazole derivatives newly designed and synthesized by our research group [24] and to investigate their possible mechanism of action.…”

Section: Introductionmentioning

confidence: 97%

See 2 more Smart Citations

Screening and Molecular Docking of Novel Benzothiazole Derivatives as Potential Antimicrobial Agents

et al. 2020

View full text Add to dashboard Cite

The burden of antibiotic resistance necessitates a continued search for new antimicrobials. We evaluated the antimicrobial activities of novel benzothiazoles synthesized by our group. Antibacterial activity was evaluated in vitro in Staphylococcus aureus, Bacillus subtilis, and Escherichia coli, while the antifungal activity was tested in Candida albicans and Aspergillus niger, and expressed as the minimum inhibitory concentration (MIC; µg/mL). MIC values of benzothiazole compounds ranged from 25 to 200 µg/mL. Compounds 3 and 4 gave high antibacterial and moderate antifungal activities, while 10 and 12 showed moderate activity against all tested organisms. In addition, some benzothiazole compounds significantly suppressed the activity of Escherichia coli dihydroorotase and inhibited the dimorphic transition of Candida albicans. Moreover, the active benzothiazole compounds induced DNA and protein leakage in Aspergillus niger spores. Molecular interactions of benzothiazole derivatives with dihydroorotase revealed the formation of hydrogen bonds with the active site residues LEU222 or ASN44. Strong hydrophobic interactions of the bulky thiazole and naphthalene rings at the entrance to the active site might interfere with the access of substrates to their binding sites, which results in dihydroorotase inhibition. Thus, inhibition of dihydroorotase might contribute to the observed antimicrobial actions of these compounds.

show abstract

Synthesis and antimicrobial activity evaluation of pyrazole derivatives containing the imidazo[2,1‐b][1,3,4]thiadiazole moiety

Yuan

Sun

et al. 2023

Archiv der Pharmazie

View full text Add to dashboard Cite

Four series of novel pyrazole derivatives (compounds 17a-m, 18a-m, 19a-g, and 20a-g) were synthesized, and their antibacterial and antifungal activities were evaluated. Most of the target compounds (17a-m, 18k-m, and 19b-g) showed strong antifungal activity and high selectivity relative to both Gram-positive and Gramnegative bacteria. Among them, compounds 17l (minimum inhibitory concentration[MIC] = 0.25 µg/mL) and 17m (MIC = 0.25 µg/mL) showed the strongest antifungal activity, being 2-and 4-fold more active than the positive controls gatifloxacin and fluconazole, respectively. In particular, compound 17l showed little cytotoxicity against human LO2 cells and did not exhibit hemolysis at ultrahigh concentrations, as did the positive control compounds gatifloxacin and fluconazole. These results indicate that these compounds are valuable for further development as antifungal agents.

show abstract

Novel substituted benzothiazole and Imidazo[2,1-b][1,3,4]Thiadiazole derivatives: Synthesis, characterization, molecular docking study, and investigation of their in vitro antileishmanial and antibacterial activities

Cited by 41 publications

References 29 publications

Synthesis, Characterization, Antimicrobial Evaluation, and Computational Investigation of Substituted Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives

Synthesis, Characterization, Antimicrobial Evaluation, and Computational Investigation of Substituted Imidazo[2,1‐b][1,3,4]Thiadiazole Derivatives

Screening and Molecular Docking of Novel Benzothiazole Derivatives as Potential Antimicrobial Agents

Synthesis and antimicrobial activity evaluation of pyrazole derivatives containing the imidazo[2,1‐b][1,3,4]thiadiazole moiety

Contact Info

Product

Resources

About