Competitive inhibition of acetylcholinesterase by several thiazolines and oxazolines

Gawron, Oscar; Keil, John G.

doi:10.1016/0003-9861(60)90057-6

Cited by 14 publications

(4 citation statements)

References 11 publications

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“…No net proton transfer from acetic acid to the heterocycle with formation of a salt bridge is predicted at this level of theory in the gas phase. Our theoretical results for this model interaction parallel the experimentally measured pK a values for 5 and 11 (see Table 1) and those reported [28] for 2-aminooxazoline (pK a = 9.37) and 2-aminothiazoline (pK a = 8.70). The calculated equilibrium constant (K d ) for the dissociation of the oxazoline complex in the gas phase is about an order of magnitude lower than that of the thiazoline complex (see Table 2), in close parallel to the corresponding K i values measured for 5 and its thio analogue 11.…”

supporting

confidence: 88%

Synthesis, Inhibition Properties, and Theoretical Study of the New Nanomolar Trehalase Inhibitor 1‐Thiatrehazolin: Towards a Structural Understanding of Trehazolin Inhibition

et al. 2005

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A new trehazolin analogue, 1-thiatrehazolin, has been synthesized from carbohydrate precursors by a highly efficient route based on our previously developed ketone/oxime ether reductive carbocyclization reaction for the construction of the cyclitol ring and an intramolecular nucleophilic displacement reaction for the construction of the thiazoline ring. 1-Thiatrehazolin is a very potent, slow, tight-binding trehalase inhibitor. A structural model for trehalase inhibition by trehazolin and its analogues, based on the experimental results and supported by theoretical calculations, is proposed.

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supporting

confidence: 88%

Synthesis, Inhibition Properties, and Theoretical Study of the New Nanomolar Trehalase Inhibitor 1‐Thiatrehazolin: Towards a Structural Understanding of Trehazolin Inhibition

et al. 2005

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“…This competitive‐type inhibition, mechanism is also presented by galantamine, dibucaine, rivastigmine and others synthetic compounds like heteroarylacrilonitriles derivatives, thiazolines and oxazolines and quinazolines.…”

Section: Resultsmentioning

confidence: 85%

Novel N‐allyl/propargyl tetrahydroquinolines: Synthesis via Three‐component Cationic Imino Diels–Alder Reaction, Binding Prediction, and Evaluation as Cholinesterase Inhibitors

et al. 2016

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New N‐allyl/propargyl 4‐substituted 1,2,3,4‐tetrahydroquinolines derivatives were efficiently synthesized using acid‐catalyzed three components cationic imino Diels–Alder reaction (70–95%). All compounds were tested in vitro as dual acetylcholinesterase and butyryl‐cholinesterase inhibitors and their potential binding modes, and affinity, were predicted by molecular docking and binding free energy calculations (∆G) respectively. The compound 4af (IC 50 = 72 μ m) presented the most effective inhibition against acetylcholinesterase despite its poor selectivity (SI = 2), while the best inhibitory activity on butyryl‐cholinesterase was exhibited by compound 4ae (IC 50 = 25.58 μ m) with considerable selectivity (SI = 0.15). Molecular docking studies indicated that the most active compounds fit in the reported acetylcholinesterase and butyryl‐cholinesterase active sites. Moreover, our computational data indicated a high correlation between the calculated ∆G and the experimental activity values in both targets.

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“…In addition, they are reported as butyrylcholinesterase and carboxylesterase inhibitors [14]. Motivated by the above-mentioned results, numerous design and synthesis efforts have been employed to develop new derivatives with more effective and safer therapeutic profiles [15,16,17,18,19,20,21,22,23,24,25,26,27,28,29,30]. Additionally, heterocycles based on a thiazoline-2-thione core may undergo several chemical reactions, including alkylation, oxidation, and cycloaddition, as a result of having two different nitrogenous and sulfurous groups [31,32,33,34,35,36,37].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, X-ray Analysis, Biological Evaluation and Molecular Docking Study of New Thiazoline Derivatives

et al. 2019

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A series of new thiazoline derivatives were synthesized. Structure analyses were accomplished employing 1H-NMR, 13C-NMR, X-ray and MS techniques. The in vitro antitumor activities were assessed against human hepatocellular carcinoma (HepG-2) and colorectal carcinoma (HCT-116) cell lines. The results revealed that the thiazolines 5b and 2c exhibited significant activity against the two cell lines. The in vitro antimicrobial screening showed that the thiazolines 2c, 5b and 5d showed promising inhibition activity against Salmonella sp. Additionally, the inhibition activity of thiazolines 2e and 5b against Escherichia coli was comparable to that of the reference compound gentamycin.

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Competitive inhibition of acetylcholinesterase by several thiazolines and oxazolines

Cited by 14 publications

References 11 publications

Synthesis, Inhibition Properties, and Theoretical Study of the New Nanomolar Trehalase Inhibitor 1‐Thiatrehazolin: Towards a Structural Understanding of Trehazolin Inhibition

Synthesis, Inhibition Properties, and Theoretical Study of the New Nanomolar Trehalase Inhibitor 1‐Thiatrehazolin: Towards a Structural Understanding of Trehazolin Inhibition

Novel N‐allyl/propargyl tetrahydroquinolines: Synthesis via Three‐component Cationic Imino Diels–Alder Reaction, Binding Prediction, and Evaluation as Cholinesterase Inhibitors

Synthesis, X-ray Analysis, Biological Evaluation and Molecular Docking Study of New Thiazoline Derivatives

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