Synthesis and antimicrobial activity evaluation of new dithiocarbamate derivatives bearing thiazole/benzothiazole rings

Yurttaş, Leyla; Özkay, Yusuf; Duran, Murat; Turan-Zitouni, Gülhan; Özdemir, Ahmet; Cantürk, Zerrin; Küçükoğlu, Kaan; Kaplancıklı, Zafer Asım

doi:10.1080/10426507.2016.1150277

Cited by 27 publications

(17 citation statements)

References 23 publications

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“…Conformational mobility of cyclic compounds is greatly limited; therefore, less rotational averaging of various chemical shift anisotropic effects occurs. Thus, the chemical shift values of the equatorial and axial hydrogens of the piperazine ring were seen at different regions as different 2H, 2H, and 4H peaks in agreement with the literature [27]. Methylene protons between carbonyl and dithioate groups were recorded as a singlet peak between 4.26 and 4.32 ppm.…”

Section: Resultssupporting

confidence: 89%

Synthesis, Characterization, and Molecular Docking Study of Some Novel Imidazole Derivatives as Potential Antifungal Agents

Işık

Çevik

Sağlık

et al. 2018

Journal of Heterocyclic Chem

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The azole pharmacophore is still regarded as a viable lead structure for the synthesis of more effective antifungal agents. In this study, two novel series of imidazole derivatives containing dithiocarbamate (5a–5g) and (benz)azolethiol (6a–6n) side chains that are structurally related to the famous antifungal azole pharmacophore were synthesized, and the structures of them were characterized by spectral (IR, 1H NMR, 13C NMR, and MS spectra) analyses. The synthesized compounds were screened in vitro antifungal activity against pathogenic strains fungi. Theoretical ADME (absorption, distribution, metabolism, and excretion) predictions were calculated for final compounds. A molecular docking study of the most active compound with target “lanosterol 14α‐demethylase” (CYP51) was performed to unravel the mode of antifungal action. Compound 5e, which features imidazole and 4‐methoxybenzyl piperazine scaffolds, showed the most promising antifungal activity with an MIC50 value of 0.78 μg/mL against C. krusei. Effect of the compound 5e against ergosterol biosynthesis was observed by LC–MS–MS method, which is based on quantification of ergosterol level in C. krusei.

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Section: Resultssupporting

confidence: 89%

Synthesis, Characterization, and Molecular Docking Study of Some Novel Imidazole Derivatives as Potential Antifungal Agents

Işık

Çevik

Sağlık

et al. 2018

Journal of Heterocyclic Chem

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“…The structural characterization of title compounds have been done by melting point, 1 H NMR, 13 C NMR and highresolution mass spectrometry (HRMS). All spectral data were consistent with the assigned structures.…”

Section: Resultsmentioning

confidence: 99%

“…Dithiocarbamates have always received the attention of the researchers round the world because of its wide utility in areas such as pharmaceuticals [1][2][3][4], intermediate product in organic synthesis [5], for the sheilding of amino groups in peptide chemistry [6,7] and as linking agents in combinatorial chemistry [8][9][10]. Organic dithiocarbamates have been extensively used as intermediate for the synthesis of structurally diverse synthetic intermediates/molecules of biological significance like antimalarial [11], anticholinergic [12], antimicrobial [13], antimitotic [14], antitubercular [15], antifungal [16], anticancer [17], antioxidant [18], antiprotozoal [19], antileprosy [20], antifolates [21], antitubulin [22], antialzheimer [23], anti-HIV [24], antipoliferative [25] and anticontraceptives [26] active agents. As a useful synthon organic dithiocarbamates have been extensively used for the synthesis of structurally diverse biological potent synthetic intermediates/molecules like isothiocyanates [27], thiourea [28], cynamide [29], dithiobenzophene [30], glycosides [31], β-sulphonamides [32], amide [33], dicarboxylates [34], thiadizoles [35], dithiolanes [36], and anhyd.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antimicrobial Activity of Dithiocarbamates of ω-Substituted (2-naphthyloxy)alkanes

et al. 2019

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A series of dithiocarbamates of ω-substituted (2-naphthyloxy) alkanes was developed through condensation of 2-(2-chloro-alkoxy)naphthalene to various kinds of aliphatic, aromatic, alicyclic, heterocyclic primary and secondary amines employing benzyl trimethyl ammonium hydroxide in catalytic quantity (Triton-B/CS2 system) afforded desired products in high yields (82-98 %). The complete series of synthesized compounds (4-48) were evaluated for antimicrobial activity through microdilution method using various bacterial and fungal strains. The antifungal and antibacterial values were estimated as MIC values. Fluconazole and ciprofloxacin [16 to 0.03 µg/ mL] were used as the standard antifungal and antibacterial drug, respectively. Out of series of evaluated compounds, some of these compounds such as compounds 28, 29, 30, 31, 32, 33 have displayed maximum potency which is comparable to standard drugs.This is an open access journal, and articles are distributed under the terms of the Attribution 4.0 International (CC BY 4.0) License. This license lets others distribute, remix, tweak, and build upon your work, even commercially, as long as they credit the author for the original creation. You must give appropriate credit, provide a link to the license, and indicate if changes were made. thiones [37], benzimidazole [38], carbamate [39], pyran [40] and flavonoids [41], etc. Apart from above mentioned activities, dithiocarba-mates of various imidazole [42], brassinin [43], rhodanine [44], quinoline [45], metal complexes [46], ammonium salts [47], etc. derivative have emerged as potent antimicrobial agents. As our group is working in drug discovery through design and synthesis of novel class of natural/semi-synthetic/ synthetic molecules especially molecules like carbamates, dithiocarbamates, dithiocarbazates, etc.

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“…A new series of 2-[4-(pyrimidin-2-yl)piperazin-1-yl]-2-oxoethyl 4-substituted piperazine-1-carbodithioate derivatives ( 2a-n ) were synthesized in this study ( Figure 3 ). Primarily, dithiocarbamate potassium salt of some secondary amines and 2-chloro- N -[4-(2-pyrimidinyl)piperazine]acetamide were gained according to well-known synthetic procedures as previously reported 43 . The structures of the final compounds were elucidated by using spectroscopic techniques.…”

Section: Resultsmentioning

confidence: 99%

Novel 1-(2-pyrimidin-2-yl)piperazine derivatives as selective monoamine oxidase (MAO)-A inhibitors

Kaya

Yurttaş

Sağlık

et al. 2017

Journal of Enzyme Inhibition and Medicinal Chemistry

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In the present study, a new series of 2-[4-(pyrimidin-2-yl)piperazin-1-yl]-2-oxoethyl 4-substituted piperazine-1-carbodithioate derivatives (2a-n) were synthesized and screened for their monoamine oxidase A and B inhibitory activity. The structures of compounds were elucidated using spectroscopic methods and some physicochemical properties of new compounds were predicted using Molinspiration and MolSoft programs. Compounds 2-[4-(pyrimidin-2-yl)piperazin-1-yl]-2-oxoethyl 4-(4-nitrophenyl)piperazine-1-carbodithioate (2j) and 2-[4-(pyrimidin-2-yl)piperazin-1-yl]-2-oxoethyl 4-benzhydrylpiperazine-1-carbodithioate (2m) exhibited selective MAO-A inhibitory activity with IC50 = 23.10, 24.14 µM, respectively. Some of the biological results were found in accordance with the obtained in silico data based on Lipinski’s fule of five.

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Synthesis and antimicrobial activity evaluation of new dithiocarbamate derivatives bearing thiazole/benzothiazole rings

Cited by 27 publications

References 23 publications

Synthesis, Characterization, and Molecular Docking Study of Some Novel Imidazole Derivatives as Potential Antifungal Agents

Synthesis, Characterization, and Molecular Docking Study of Some Novel Imidazole Derivatives as Potential Antifungal Agents

Synthesis and Antimicrobial Activity of Dithiocarbamates of ω-Substituted (2-naphthyloxy)alkanes

Novel 1-(2-pyrimidin-2-yl)piperazine derivatives as selective monoamine oxidase (MAO)-A inhibitors

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