Substituted cinnamic anhydrides act as selective inhibitors of acetylcholinesterase

Gießel, Josephine M.; Serbian, Immo; Loesche, Anne

doi:10.1016/j.bioorg.2019.103058

Cited by 5 publications

(2 citation statements)

References 36 publications

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“…For example, cinnamic anhydrides were synthesized and determined the inhibition impact on AChE enzyme activity. It was found that K i constants in ranging from 0.54±0.01‐17.81±0.95 μM . In another study, dipropargyl substituted diphenylpyrimidines were synthesized and investigated for the AChE and mono‐amine oxidase enzyme activity.…”

Section: Resultsmentioning

confidence: 99%

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New Isoindole‐1,3‐dione Substituted Sulfonamides as Potent Inhibitors of Carbonic Anhydrase and Acetylcholinesterase: Design, Synthesis, and Biological Evaluation

et al. 2019

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Herein, a series of isoindole‐1,3‐dione substituted sulfonamide derivatives (3, 4 a–k) were designed, synthesized, and biologically evaluated, as inhibitors of carbonic anhydrase (CA) and acetylcholinesterase (AChE). CA and AChE inhibitory activities of newly synthesized isoindole‐1,3‐dione substituted sulfonamides compounds (3, 4 a–k) towards the hCA I, II, and AChE were evaluated utilizing the Verpoorte's and Ellman's assays and checked against that of standard inhibitors, acetazolamide (AAZ) and tacrine (TAC). The developed compounds (3, 4 a–k) showed the potent hCA isoenzyme inhibitory effect with Ki constants ranging from 7.96 to 48.34 nM, compared to AAZ (Kis; 436.20 nM for hCA I and 93.53 nM for hCA II). Among these derivatives; 1,3‐dioxo‐1,3‐dihydroisobenzofuran‐5‐carbocyclic acid (3) and benzyl‐1,3‐dioxo‐2‐(4‐sulfomophenyl)isoindoline‐5‐carboxylate (4 i) determined to be effective AChE inhibitors (Kis, 103.51 and 108.92 nM, respectively); these compounds were almost as potent to TAC (Ki, 109.75 nM). Furthermore, molecular docking studies of derivatives 3 and 4 i were carried out utilizing the crystal structures of hCA I (PDB Code: 4WR7), II (PDB Code: 4HT0) isozymes and AChE (PDB Code: 4EY7) receptors to study their binding interactions.

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Section: Resultsmentioning

confidence: 99%

“…It was found that K i constants in ranging from 0.54 � 0.01-17.81 � 0.95 μM. [39] In another study, dipropargyl substituted diphenylpyrimidines were synthesized and investigated for the AChE and mono-amine oxidase enzyme activity. These derivatives showed potent AChE inhibition.…”

Section: Biological Evaluationmentioning

confidence: 99%