| Yazarlar |
Mustafa Er
Karabük Üniversitesi, Türkiye |
|
Arif Özer
|
|
Şahin Direkel
Giresun Üniversitesi, Türkiye |
Doç. Dr. Tuncay KARAKURT
Kırşehir Ahi Evran Üniversitesi, Türkiye |
|
Hakan Tahtacı
Karabük Üniversitesi, Türkiye |
| Özet |
| In this study, we synthesized new imidazo[2,1-b][1,3,4]thiadiazole derivatives containing benzothiazole group. To this end, we firstly obtained the benzo[d]thiazol-2-ylthio/oxy acetonitrile compounds (3a,b), the starting materials, in high yields (82% and 87%, respectively). Then, we synthesized the 2-amino-1,3,4-thiadiazole derivatives (4a,b) from the reaction of these nitrile derivatives (3a,b) with thio-semicarbazide in trifluoroacetic acid (TFA) (in yields of 83% and 84%). Finally, we synthesized the imidazo [2,1-b][1,3,4]thiadiazole derivatives (5-24) containing benzothiazole group, which are the target compounds, from reactions of 2-amino-1,3,4-thiadiazole derivatives (4a,b) with phenacyl bromide derivatives (in yields of 53%-73%). All of the compounds synthesized were characterized with H-1 NMR, C-13 NMR, FT-IR, elemental analysis, and mass spectroscopy. Antileishmanial and antibacterial activity tests were applied to the compounds synthesized in the study. It was observed that compound 8 had the highest antileishmanial activity (MIC = 10 000 mu g/mL). Also, compounds 7 and 17 were found to be effective at the highest concentration studied (MIC = 20 000 mu g/mL). In terms of antibacterial activity, compounds 4b and 7 were found to be the most effective compounds against Escherichia coli (MIC = 625 mu g/mL). Theoretical calculations were performed to support the experimental results. To this end, we performed Molecular Docking studies to determine whether or not the compounds (4a, 4b, 7 and 13) optimized with Gaussian09 using the DET/B3LYP/6-31G(d,p) theory, which is a quantum chemical calculation, could be an inhibitor agent for the 2eg7 Escherichia coli protein structure. Also, we investigated the relationship between the calculated HOMO values of these four ligands and docking studies. (C) 2019 Elsevier B.V. All rights reserved. |
| Anahtar Kelimeler |
| Benzothiazole | Imidazo[2,1-b][1,3,4]thiadiazole | Biological activity | Molecular docking | HOMO |
| Makale Türü | Özgün Makale |
| Makale Alt Türü | SSCI, AHCI, SCI, SCI-Exp dergilerinde yayımlanan tam makale |
| Dergi Adı | JOURNAL OF MOLECULAR STRUCTURE |
| Dergi ISSN | 0022-2860 |
| Dergi Tarandığı Indeksler | SCI-Expanded |
| Dergi Grubu | Q3 |
| Makale Dili | İngilizce |
| Basım Tarihi | 10-2019 |
| Cilt No | 1194 |
| Sayfalar | 284 / 296 |
| Doi Numarası | 10.1016/j.molstruc.2019.05.104 |
| Makale Linki | https://linkinghub.elsevier.com/retrieve/pii/S0022286019306763 |
| Atıf Sayıları | |
| WoS | 35 |
