2019
DOI: 10.3390/ijms20071524
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Novel Benzene-Based Carbamates for AChE/BChE Inhibition: Synthesis and Ligand/Structure-Oriented SAR Study

Abstract: A series of new benzene-based derivatives was designed, synthesized and comprehensively characterized. All of the tested compounds were evaluated for their in vitro ability to potentially inhibit the acetyl- and butyrylcholinesterase enzymes. The selectivity index of individual molecules to cholinesterases was also determined. Generally, the inhibitory potency was stronger against butyryl- compared to acetylcholinesterase; however, some of the compounds showed a promising inhibition of both enzymes. In fact, t… Show more

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Cited by 18 publications
(21 citation statements)
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“…On the other hand, tacrine is only about four times better at the inhibition of AChE [53]. However, there have been published several studies describing the less significant selectivity of carbamate inhibitors towards AChE or BChE [24,54,55,56,57]. As mentioned above, reaching the site of action is key for drugs; in the case of anti-AD drugs, this is penetration into the CNS via the BBB.…”
Section: Resultsmentioning
confidence: 99%
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“…On the other hand, tacrine is only about four times better at the inhibition of AChE [53]. However, there have been published several studies describing the less significant selectivity of carbamate inhibitors towards AChE or BChE [24,54,55,56,57]. As mentioned above, reaching the site of action is key for drugs; in the case of anti-AD drugs, this is penetration into the CNS via the BBB.…”
Section: Resultsmentioning
confidence: 99%
“…In real-world drug discovery, a model with ‘good retrospective performance does not necessarily exhibit good prospective performance’ (Kubinyi paradox) [62]. Restricting ourselves to single numerical measure of qcv2/q2test can be misleading; therefore, we proposed ‘consensus-based’ pharmacophore generation using stochastic model validation (SMV) methodology [9,24,44]. Firstly, the original dataset of 25 compounds was recurrently sampled into 17 / 8 training/test subgroups (ratio 2 to 1).…”
Section: Resultsmentioning
confidence: 99%
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“…The molecular distribution of the experimental-based (FCS) and virtual-derived (VCS) compounds/models might be graphically displayed using the human friendly 2D/3D plots, e.g., in the procedure called Principal Component Analysis (PCA) [ 62 ]. PCA is a linear projection method designed to model multivariate data with a relatively small number of so-called principal components (scores and loadings) constructed in order to maximize the variance description of input data [ 63 ]. The PCA model with f principal components for a data matrix X can be presented as follows: X = TP T + E where X is a data matrix with m objects and n variables, T is the score matrix with dimensions ( m × f ), P T is a transposed matrix of loadings with dimensions ( f × n ) and E is a matrix of the residual variance ( m × n ) that is not explained by the first f principal components.…”
Section: Methodsmentioning
confidence: 99%
“…Synthesis of 4-CMC was accomplished according to a modified Bak et al procedure (Bak et al, 2019 ) ( Supplementary Scheme S3 in the ESI). The reaction was performed starting from commercially available 4-chloropropiophenone in a series of α-bromination and amination reactions and the desired product was obtained in a 68% overall yield.…”
Section: Methodsmentioning
confidence: 99%