The synthesis of (<i>Z</i>)-4-oxo-4-(arylamino)but-2-enoic acids derivatives and determination of their inhibition properties against human carbonic anhydrase I and II isoenzymes

Oktay, Koray; Köse, Leyla Polat; Şendil, Kıvılcim; Gültekin, M. S.; Gülçın, İlhami; Supuran, Claudiu T.

doi:10.3109/14756366.2015.1071808

Cited by 23 publications

(17 citation statements)

References 89 publications

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“…The threecomponent condensation reactions come to an end within 2-4 h at 65-70 C. The synthesised compounds were crystalline and their structure was confirmed by spectral and physico-chemical methods, among which were 1 H and 13 C NMR spectroscopies. Inhibitors of carbonic anhydrase enzymes (CAIs) have a large number of applications in therapy, such as anticancer, antiglaucoma and anti-osteoporosis agents 85 . The classical CAIs are the primary sulphonamides, which are in clinical use for more than 50 years as diuretics and systemically acting antiglaucoma drugs.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of N-alkyl (aril)-tetra pyrimidine thiones and investigation of their human carbonic anhydrase I and II inhibitory effects

Sujayev

Köse

Garibov

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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Section: Resultsmentioning

confidence: 99%

Synthesis of N-alkyl (aril)-tetra pyrimidine thiones and investigation of their human carbonic anhydrase I and II inhibitory effects

Sujayev

Köse

Garibov

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…In addition, in humans, CA isoforms exist in a wide variety of tissues including the reproductive tract, gastrointestinal tract, kidneys, lungs, CNS, eyes, and skin . Thus far, seven types of CA families have been recorded: the α‐, β‐, γ‐, δ ‐, ζ‐, n‐, and θ‐CAs .…”

Section: Introductionmentioning

confidence: 99%

Discovery of potent carbonic anhydrase, acetylcholinesterase, and butyrylcholinesterase enzymes inhibitors: The new amides and thiazolidine-4-ones synthesized on an acetophenone base

Taslimi

Osmanova

Gülçın

et al. 2017

J Biochem Mol Toxicol

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Compounds containing nitrogen and sulfur atoms can be widely used in various fields, including industry, medicine, biotechnology, and chemical technology. Among them, amides of acids and heterocyclic compounds have an important place. These amides and thiazolidine-4-ones showed good inhibitory action against butyrylcholinesterase (BChE), acetylcholinesterase (AChE), and human carbonic anhydrase isoforms. AChE exists at high concentrations in the brain and red blood cells. BChE is an important enzyme that is plentiful in the liver, and it is released into the blood in a soluble form. They were demonstrated to have effective inhibition profiles with K values of 23.76-102.75 nM against hCA I, 58.92-136.64 nM against hCA II, 1.40-12.86 nM against AChE, and 9.82-52.77 nM against BChE. On the other hand, acetazolamide showed K value of 482.63 ± 56.20 nM against hCA I, and 1019.60 ± 163.70 nM against hCA II. Additionally, Tacrine inhibited AChE and BChE, showing K values of 397.03 ± 31.66 and 210.21 ± 15.98 nM, respectively.

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“…The carbonic anhydrases (CA) (EC. 4.2.1.1) are metalloenzyme family, available from prokaryotes to eukaryotes ubiquitously expressed in living organisms and contain the zinc ion (Zn 2+) in their active site –. Up to now, six genetically distinct CA families are known, including the α‐, β‐, γ‐, δ‐, ζ‐, and η‐CA classes –.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, carbonic anhydrase I and II isoenzymes inhibition properties, and antibacterial activities of novel tetralone-based 1,4-benzothiazepine derivatives

Ceylan

Koçyiğit

Usta

et al. 2016

J Biochem Mol Toxicol

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Benzothiazepine compounds have a wide range of applications such as antibacterial, antidepressants, anticonvulsants, antihypertensives, antibiotics, antifungal, hypnotic, enzyme inhibitors, antitumor, anticancer and anti-HIV agents. In this study, the synthesis of novel tetralone-based benzothiazepine derivatives (1-16) and their in vitro antibacterial activity and human carbonic anhydrase isoenzymes I and II (hCA I and II) inhibitory effects were investigated. Both isoenzymes were purified by sepharose-4B-l-tyrosine-sulfanilamide affinity chromatography from fresh human red blood cells. All compounds demonstrated the low nanomolar inhibitory effects on both isoenzymes using esterase activity. Benzothiazepine derivative 2 demonstrated the best hCA I inhibitory effect with K value of 18.19 nM. Also, benzothiazepine derivative 7 showed the best hCA II inhibitory effect with K value of 11.31 nM. On the other hand, acetazolamide clinically used as CA inhibitor, showed K value of 19.92 nM against hCA I and 33.60 nM against hCA II, respectively.

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The synthesis of (Z)-4-oxo-4-(arylamino)but-2-enoic acids derivatives and determination of their inhibition properties against human carbonic anhydrase I and II isoenzymes

Cited by 23 publications

References 89 publications

Synthesis of N-alkyl (aril)-tetra pyrimidine thiones and investigation of their human carbonic anhydrase I and II inhibitory effects

Synthesis of N-alkyl (aril)-tetra pyrimidine thiones and investigation of their human carbonic anhydrase I and II inhibitory effects

Discovery of potent carbonic anhydrase, acetylcholinesterase, and butyrylcholinesterase enzymes inhibitors: The new amides and thiazolidine-4-ones synthesized on an acetophenone base

Synthesis, carbonic anhydrase I and II isoenzymes inhibition properties, and antibacterial activities of novel tetralone-based 1,4-benzothiazepine derivatives

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