Synthesis and in vitro evaluation of new derivatives of 2-substituted-6-fluorobenzo[d]thiazoles as cholinesterase inhibitors

Imramovský, Aleš; Pejchal, Vladimír; Štěpánková, Šárka; Vorčáková, Katarína; Jampílek, Josef; Vančo, Ján; Šimůnek, Petr; Královec, Karel; Brůčková, Lenka; Mandíková, Jana; Trejtnar, František

doi:10.1016/j.bmc.2013.01.052

Cited by 39 publications

(23 citation statements)

References 47 publications

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“…Compounds 139(a,b) showed, the highest AChE-inhibiting activity, while compound (139c) showed the highest BChE inhibition. From SAR, n-propyl chain is necessary for both types of AChE/ BChE inhibitors, for higher AChE-inhibiting activity, long-chain alkyl substitution of the carbamate ester enhance the BChE inhibitors [174]. Neumaier et al, reported structurally versatile fluoroethoxy-substituted BTA derivatives as possible candidates for (140,141) showed low binding affinity to Ab(1e40) amyloidplaque (Ki > 600 nM).…”

Section: Bta As Anti-ad Agentsmentioning

confidence: 98%

“…All these BTA derivatives exhibited good DPPH radical scavenging potential with EC 50 values ranging from 20 to 60 mM as compared to ascorbic acid (40.28 mM). Compound Compounds (173,174) showed the highest percentage of free radical scavenging activity [204]. Bis-benzothiazole-pyrazoline derivatives were reported and evaluated in vitro for their antioxidant activity by ferric ion reduction and DPPH methods.…”

Section: Bta As Antioxidant Agentsmentioning

confidence: 99%

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A comprehensive review in current developments of benzothiazole-based molecules in medicinal chemistry

Keri

Patil

et al. 2015

European Journal of Medicinal Chemistry

484

238

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Section: Bta As Anti-ad Agentsmentioning

confidence: 98%

Section: Bta As Antioxidant Agentsmentioning

confidence: 99%

A comprehensive review in current developments of benzothiazole-based molecules in medicinal chemistry

Keri

Patil

et al. 2015

European Journal of Medicinal Chemistry

484

238

View full text Add to dashboard Cite

“…The cholinergic deficiency in Alzheimer's disease is related to a decrease in the concentration of ACh and its levels can be controlled via AChE inhibitors. An increase in the ACh concentration can result in the alleviation of the symptoms of several diseases such as Parkinson's, ataxia, senile dementia, myasthenia gravis, and Alzheimer's disease (Bitencourt, Freitas, & Rittner, ; Ehrenstein, Galdzicki, & Lange, ; Imramovský et al, ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, molecular modeling studies, ADME prediction of arachidonic acid carbamate derivatives, and evaluation of their acetylcholinesterase activity

Kalin

Kılıç

Arslan

et al. 2019

Drug Development Research

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In this work, a series of novel anandamide units containing carbamate were designed and synthesized. All the derivatives were evaluated in vitro for their inhibitory potential against the electric eel acetylcholinesterase enzyme (AChE) and showed reversible inhibitions. The compounds 7a, 7d, 7e, and 7f are mixed inhibitors of AChE, while the compounds 7b, 7c, and 7g are uncompetitive (Ki in the range 0.93–8.86 μM). The kinetic studies revealed that compounds 7b, 7c, 7f, and 7g inhibit considerably AChE activity. Molecular docking analyses were made to evaluate the binding type and interactions of the synthesized compounds to the ligand‐binding site of hAChE. It was observed that the docking results were in parallel with the in vitro results. The adsorption, distribution, metabolism, and excretion properties were computed for the compounds, and were found within the acceptable range. This study suggests the compounds 7b, 7c, 7f, and 7g identified as novel reversible AChE inhibitors may be useful lead compounds for the treatment of Alzheimer's disease.

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“…Molecular skeleton of these compounds can serve as a unique and versatile playground for further synthetic modification and thus also for an experimental drug design. The studies of structure-activity relationships interestingly reveal that a slight variation of the structure of substituent group at C-2 position commonly results in significant change of its biological activity (Pejchal et al, 2011a, b;Imramovsky et al, 2013).…”

Section: Introductionmentioning

confidence: 99%

Synthesis, structural characterization, antimicrobial and antifungal activity of substituted 6-fluorobenzo[d]thiazole amides

2015

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A series of novel 1-[(1R)-1-(6-fluoro-1,3-benzothiazol-2-yl)ethyl]-3-substituted phenyl amides was synthesized by the condensation reaction of (1R)-1-(6-fluoro-1,3-benzothiazol-2-yl)ethanamine with substituted benzoyl chlorides under mild conditions. Their structures were confirmed by 1 H NMR, 13 C NMR and 19 F NMR spectra, elemental analyses and in three cases also by single-crystal X-ray diffraction techniques. The optical activities were confirmed by optical rotation measurements. All the synthesized compounds were screened for antibacterial and antifungal activity against a variety of bacterial and fungal strains. Some of the compounds reveal antibacterial and antifungal activity comparable or slightly better to that of chloramphenicol, cefoperazone and amphotericin B used as medicinal standards.

show abstract

Synthesis and in vitro evaluation of new derivatives of 2-substituted-6-fluorobenzo[d]thiazoles as cholinesterase inhibitors

Cited by 39 publications

References 47 publications

A comprehensive review in current developments of benzothiazole-based molecules in medicinal chemistry

A comprehensive review in current developments of benzothiazole-based molecules in medicinal chemistry

Synthesis, molecular modeling studies, ADME prediction of arachidonic acid carbamate derivatives, and evaluation of their acetylcholinesterase activity

Synthesis, structural characterization, antimicrobial and antifungal activity of substituted 6-fluorobenzo[d]thiazole amides

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