Intermolecular amination of allylic and benzylic alcohols leads to effective inhibitions of acetylcholinesterase enzyme and carbonic anhydrase I and II isoenzymes

Atmaca, Ufuk; Yıldırım, Alper; Taslimi, Parham; Çelik, Seda Tuncel; Gülçın, İlhami; Supuran, Claudiu T.

doi:10.1002/jbt.22173

Cited by 31 publications

(16 citation statements)

References 75 publications

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“…These reports prompted us to explore this reaction in more detail. In our previous studies, we investigated the reactions of various carboxylic acids, alkenes and allyl or benzyl alcohols with CSI [43][44][45][46]. As a continuation of these studies, we performed one-pot synthesis of the titled compounds by optimizing the reaction of CSI with epoxides in different solvents under mild conditions.…”

Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis of Oxazolidinones and Five-Membered Cyclic Carbonates from Epoxides and Chlorosulfonyl isocyanate: Theoretical Evidence for the Asynchronous Concerted Pathway

Demir¹,

Sarı²,

Çetinkaya³

et al. 2020

Preprint

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The one-pot reaction of chlorosulfonyl isocyanate (CSI) with epoxides having substituted phenyl, benzyl and fused cyclic alkyl groups in different solvents under mild reaction conditions without additives and catalysts was studied. Oxazolidinones and five-membered cyclic carbonates were obtained with a ratio close to (1:1) in the cyclization reactions. The best reaction conversion for the synthesis of these compounds was carried out in dichloromethane (DCM). The method presented here has distinct advantageous over the existing methods such as one-pot reaction, shorter reaction times, metal-free reagent, good yields and very simple purification method. The mechanism for the cycloaddition reactions has been elucidated using density functional theory (DFT) method at the M06-2X/6-31+G(d,p) level. The investigation of the potential energy surfaces associated with two possible channels leading to oxazolidinones and five-membered cyclic carbonates revealed that the cycloaddition reaction takes place through an asynchronous concerted mechanism in gas phase and in DCM.

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Section: Introductionmentioning

confidence: 99%

One-Pot Synthesis of Oxazolidinones and Five-Membered Cyclic Carbonates from Epoxides and Chlorosulfonyl isocyanate: Theoretical Evidence for the Asynchronous Concerted Pathway

Demir¹,

Sarı²,

Çetinkaya³

et al. 2020

Preprint

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“…The elucidation of metabolic mechanisms of inhibitors is a guide for biochemists. [59,60] The chemical structure of sesamol is given in Figure 1. It was known that sesamol could cross the blood-brain barrier.…”

Section: Resultsmentioning

confidence: 99%

The inhibition profile of sesamol against α-glycosidase and acetylcholinesterase enzymes

Topal

2019

International Journal of Food Properties

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Sesamol (1,3-benzodioxol-5-ol) is found in the oilseed product, sesame. In our study, the inhibitory effects of sesamol compound on acetylcholinesterase and α-glycosidase enzymes were evaluated. Another aim of this study was to compare the inhibitory effects of sesamol to acarbose for α-glycosidase enzyme and tacrine for acetylcholinesterase (AChE). Sesamol exhibited noncompetitive inhibition for both metabolic enzymes. IC 50 values for AChE and αglycosidase enzymes were calculated as 86.63 nM and 99.00 nM, respectively. On the other hand, K i values were calculated as 46.68 nM and 75.33 nM for AChE and α-glycosidase enzymes, respectively. According to the obtained results showed effective inhibition at low concentrations. ARTICLE HISTORY

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“…Our research group has previously carried out the reaction of the sulfamoyl chlorides with the alcohols and amines . The amination of allylic or benzylic alcohols with CSI was efficiently carried out and sulfamoyl chloride at low temperature was provided without any catalyst or additives.…”

Section: Resultsmentioning

confidence: 99%

Novel sulfamate derivatives of menthol: Synthesis, characterization, and cholinesterases and carbonic anhydrase enzymes inhibition properties

Daryadel

Atmaca

Taslimi

et al. 2018

Archiv der Pharmazie

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Sulfamates have a large spectrum of biological activities including enzyme inhibition. Eight sulfamates derived from menthol (2a-h) were synthesized. Also, in the other section of this study, novel sulfamate derivatives of menthol were tested against some metabolic enzymes including acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and carbonic anhydrase I and II enzymes (hCAs I and II). The newly synthesized novel menthol sulfamate and menthol carbonyl sulfamate derivatives showed K i values in the range of 34.37 ± 8.17 to 53.40 ± 10.61 nM against hCA I, 12.91 ± 4.57 to 38.67 ± 6.22 nM against hCA II, 111.17 ± 52.36 to 522.86 ± 120.08 nM against AChE, and 50.01 ± 11.73 to 109.63 ± 50.08 nM against BChE. As a result, the novel menthol sulfamate and menthol carbonyl sulfamate derivatives can be promising Alzheimer's disease drug candidates and novel hCA I and hCA II enzymes inhibitors. K E Y W O R D S acetylcholinesterase, butyrylcholinesterase, carbonic anhydrase, enzyme inhibition, sulfamate HCO 3 − buffer method predominantly controls maintenance of an Arch Pharm Chem Life Sci. 2018;351:e1800209. wileyonlinelibrary.com/journal/ardp

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Intermolecular amination of allylic and benzylic alcohols leads to effective inhibitions of acetylcholinesterase enzyme and carbonic anhydrase I and II isoenzymes

Cited by 31 publications

References 75 publications

One-Pot Synthesis of Oxazolidinones and Five-Membered Cyclic Carbonates from Epoxides and Chlorosulfonyl isocyanate: Theoretical Evidence for the Asynchronous Concerted Pathway

One-Pot Synthesis of Oxazolidinones and Five-Membered Cyclic Carbonates from Epoxides and Chlorosulfonyl isocyanate: Theoretical Evidence for the Asynchronous Concerted Pathway

The inhibition profile of sesamol against α-glycosidase and acetylcholinesterase enzymes

Novel sulfamate derivatives of menthol: Synthesis, characterization, and cholinesterases and carbonic anhydrase enzymes inhibition properties

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