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Keywords = (3-benzyl-5-hydroxyphenyl)carbamate

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6 pages, 788 KiB  
Proceeding Paper
Benzyl Carbamates of 4-Aminosalicylanilides as Possible BACE1 Modulators
by Petra Majerova, Dominika Pindjakova, Timotej Jankech, Ivana Gerhardtova, Jiri Kos, Andrej Kovac and Josef Jampilek
Chem. Proc. 2022, 12(1), 40; https://doi.org/10.3390/ecsoc-26-13680 - 17 Nov 2022
Viewed by 1549
Abstract
Recently, a series of thirty-eight 4-{[(benzyloxy)carbonyl]amino}-2-hydroxybenzoic acid amides designed as potential acetyl- and butyrylcholinesterase (AChE/BChE) inhibitors were described as potential drugs to alleviate the symptoms of Alzheimer’s disease (AD). Some of these compounds have shown promise for inhibiting either AChE or BChE. Since [...] Read more.
Recently, a series of thirty-eight 4-{[(benzyloxy)carbonyl]amino}-2-hydroxybenzoic acid amides designed as potential acetyl- and butyrylcholinesterase (AChE/BChE) inhibitors were described as potential drugs to alleviate the symptoms of Alzheimer’s disease (AD). Some of these compounds have shown promise for inhibiting either AChE or BChE. Since these compounds are structurally similar to agents inhibiting beta-site amyloid precursor protein cleaving enzyme 1 (BACE1), the aim of the contribution was to verify how our compounds were able to affect this enzyme, which, when inhibited, blocks the formation of amyloid-β, but whose inhibition is associated with significant adverse effects in humans. At a concentration of 10 µM, only benzyl {4-[(4-fluorophenyl)carbamoyl]-3-hydroxyphenyl}carbamate was found to show approximately 28% inhibition of BACE1 activity. Full article
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29 pages, 4248 KiB  
Article
SAR-mediated Similarity Assessment of the Property Profile for New, Silicon-Based AChE/BChE Inhibitors
by Andrzej Bak, Hana Pizova, Violetta Kozik, Katarina Vorcakova, Jiri Kos, Jakub Treml, Klara Odehnalova, Michal Oravec, Ales Imramovsky, Pavel Bobal, Adam Smolinski, Zdeněk Trávníček and Josef Jampilek
Int. J. Mol. Sci. 2019, 20(21), 5385; https://doi.org/10.3390/ijms20215385 - 29 Oct 2019
Cited by 12 | Viewed by 4346
Abstract
A set of 25 novel, silicon-based carbamate derivatives as potential acetyl- and butyrylcholinesterase (AChE/BChE) inhibitors was synthesized and characterized by their in vitro inhibition profiles and the selectivity indexes (SIs). The prepared compounds were also tested for their inhibition potential on photosynthetic electron [...] Read more.
A set of 25 novel, silicon-based carbamate derivatives as potential acetyl- and butyrylcholinesterase (AChE/BChE) inhibitors was synthesized and characterized by their in vitro inhibition profiles and the selectivity indexes (SIs). The prepared compounds were also tested for their inhibition potential on photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. In fact, some of the newly prepared molecules revealed comparable or even better inhibitory activities compared to the marketed drugs (rivastigmine or galanthamine) and commercially applied pesticide Diuron®, respectively. Generally, most compounds exhibited better inhibition potency towards AChE; however, a wider activity span was observed for BChE. Notably, benzyl N-[(1S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(2-hydroxyphenyl)carbamoyl]ethyl]-carbamate (2) and benzyl N-[(1S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(3-hydroxyphenyl)carbamoyl]ethyl]-carbamate (3) were characterized by fairly high selective indexes. Specifically, compound 2 was prescribed with the lowest IC50 value that corresponds quite well with galanthamine inhibition activity, while the inhibitory profiles of molecules 3 and benzyl-N-[(1S)-2-[(tert-butyldimethylsilyl)oxy]-1-[(4-hydroxyphenyl)carbamoyl]ethyl]carbamate (4) are in line with rivastigmine activity. Moreover, a structure–activity relationship (SAR)-driven similarity evaluation of the physicochemical properties for the carbamates examined appeared to have foreseen the activity cliffs using a similarity–activity landscape index for BChE inhibitory response values. The ‘indirect’ ligand-based and ‘direct’ protein-mediated in silico approaches were applied to specify electronic/steric/lipophilic factors that are potentially valid for quantitative (Q)SAR modeling of the carbamate analogues. The stochastic model validation was used to generate an ‘average’ 3D-QSAR pharmacophore pattern. Finally, the target-oriented molecular docking was employed to (re)arrange the spatial distribution of the ligand property space for BChE and photosystem II (PSII). Full article
(This article belongs to the Special Issue QSAR and Chemoinformatics Tools for Modeling)
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14 pages, 8559 KiB  
Article
Discovery of (3-Benzyl-5-hydroxyphenyl)carbamates as New Antitubercular Agents with Potent In Vitro and In Vivo Efficacy
by Ya-Juan Cheng, Zhi-Yong Liu, Hua-Ju Liang, Cui-Ting Fang, Niu-Niu Zhang, Tian-Yu Zhang and Ming Yan
Molecules 2019, 24(10), 2021; https://doi.org/10.3390/molecules24102021 - 27 May 2019
Cited by 6 | Viewed by 4474
Abstract
A series of 3-amino-5-benzylphenol derivatives were designed and synthesized. Among them, (3-benzyl-5-hydroxyphenyl)carbamates were found to exert good inhibitory activity against M. tuberculosis H37Ra, H37Rv and clinically isolated multidrug-resistant M. tuberculosis strains (MIC = 0.625–6.25 μg/mL). The privileged compounds 3i and 3l showed moderate [...] Read more.
A series of 3-amino-5-benzylphenol derivatives were designed and synthesized. Among them, (3-benzyl-5-hydroxyphenyl)carbamates were found to exert good inhibitory activity against M. tuberculosis H37Ra, H37Rv and clinically isolated multidrug-resistant M. tuberculosis strains (MIC = 0.625–6.25 μg/mL). The privileged compounds 3i and 3l showed moderate cytotoxicity against cell line A549. Compound 3l also exhibited potent in vivo inhibitory activity on a mouse infection model via the oral administration. The results demonstrated 3-hydroxyphenylcarbamates as a class of new antitubercular agents with good potential. Full article
(This article belongs to the Special Issue Tuberculosis Drug Discovery and Development)
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26 pages, 3443 KiB  
Article
Proline-Based Carbamates as Cholinesterase Inhibitors
by Hana Pizova, Marketa Havelkova, Pavel Bobal, Sarka Stepankova, Tereza Kauerova, Andrzej Bak, Peter Kollar, Violetta Kozik, Michal Oravec, Ales Imramovsky and Josef Jampilek
Molecules 2017, 22(11), 1969; https://doi.org/10.3390/molecules22111969 - 14 Nov 2017
Cited by 19 | Viewed by 5684
Abstract
Series of twenty-five benzyl (2S)-2-(arylcarbamoyl)pyrrolidine-1-carboxylates was prepared and completely characterized. All the compounds were tested for their in vitro ability to inhibit acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), and the selectivity of compounds to individual cholinesterases was determined. Screening of the cytotoxicity [...] Read more.
Series of twenty-five benzyl (2S)-2-(arylcarbamoyl)pyrrolidine-1-carboxylates was prepared and completely characterized. All the compounds were tested for their in vitro ability to inhibit acetylcholinesterase (AChE) and butyrylcholinesterase (BChE), and the selectivity of compounds to individual cholinesterases was determined. Screening of the cytotoxicity of all the compounds was performed using a human monocytic leukaemia THP-1 cell line, and the compounds demonstrated insignificant toxicity. All the compounds showed rather moderate inhibitory effect against AChE; benzyl (2S)-2-[(2-chlorophenyl)carbamoyl]pyrrolidine-1-carboxylate (IC50 = 46.35 μM) was the most potent agent. On the other hand, benzyl (2S)-2-[(4-bromophenyl)-] and benzyl (2S)-2-[(2-bromophenyl)carbamoyl]pyrrolidine-1-carboxylates expressed anti-BChE activity (IC50 = 28.21 and 27.38 μM, respectively) comparable with that of rivastigmine. The ortho-brominated compound as well as benzyl (2S)-2-[(2-hydroxyphenyl)carbamoyl]pyrrolidine-1-carboxylate demonstrated greater selectivity to BChE. The in silico characterization of the structure–inhibitory potency for the set of proline-based carbamates considering electronic, steric and lipophilic properties was provided using comparative molecular surface analysis (CoMSA) and principal component analysis (PCA). Moreover, the systematic space inspection with splitting data into the training/test subset was performed to monitor the statistical estimators performance in the effort to map the probability-guided pharmacophore pattern. The comprehensive screening of the AChE/BChE profile revealed potentially relevant structural and physicochemical features that might be essential for mapping of the carbamates inhibition efficiency indicating qualitative variations exerted on the reaction site by the substituent in the 3′-/4′-position of the phenyl ring. In addition, the investigation was completed by a molecular docking study of recombinant human AChE. Full article
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