Synthesis and investigation of anticancer, antibacterial activities and carbonic anhydrase, acetylcholinesterase inhibition profiles of novel (3aR,4S,7R,7aS)-2-[4-[1-acetyl-5-(aryl/heteroaryl)-4,5-dihydro-1H-pyrazol-3-yl]phenyl]-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-diones

Koçyiğit, Ümit M.; Budak, Yakup; Gürdere, Meliha Burcu; Dürü, Neşe; Taslimi, Parham; Gülçın, İlhami; Ceylan, Mustafa

doi:10.1007/s00706-019-2350-z

Cited by 33 publications

(17 citation statements)

References 83 publications

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“…Novel N -acetyl pyrazolines bearing a tetrahydro-methanoisoindolodione unit have been synthesized and investigated for their anticancer activities by Kocyigit et al Compound 35 ( Figure 13 ) was found to be the most potent among 14 derivatives, displaying moderate IC 50 value of 50.05 μM against C6 rat gliocarcinoma cells [ 91 ].…”

Section: 2-pyrazolinesmentioning

confidence: 99%

Pyrazoline Hybrids as Promising Anticancer Agents: An Up-to-Date Overview

Matiadis

Sagnou

2020

IJMS

104

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Pyrazolines are five-membered heterocycles possessing two adjacent nitrogens. They have attracted significant attention from organic and medicinal chemists due to their potent biological activities and the numerous possibilities for structural diversification. In the last decade, they have been intensively studied as targets for potential anticancer therapeutics, producing a steady yearly rise in the number of published research articles. Many pyrazoline derivatives have shown remarkable cytotoxic activities in the form of heterocyclic or non-heterocyclic based hybrids, such as with coumarins, triazoles, and steroids. The enormous amount of related literature in the last 5 years prompted us to collect all these published data from screening against cancer cell lines, or protein targets like EGFR and structure activity relationship studies. Therefore, in the present review, a comprehensive account of the compounds containing the pyrazoline nucleus will be provided. The chemical groups and the structural modifications responsible for the activity will be highlighted. Moreover, emphasis will be given on recent examples from the literature and on the work of research groups that have played a key role in the development of this field.

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Section: 2-pyrazolinesmentioning

confidence: 99%

Pyrazoline Hybrids as Promising Anticancer Agents: An Up-to-Date Overview

Matiadis

Sagnou

2020

IJMS

104

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“…Acetylcholinesterase (AChE), which is expressed in brain tissues and which operates to characterize ACh functioning in the central neural system alike in a balanced way, is a very efficient enzyme to hydrolyze ACh. [12][13][14][15][16] α-Glycosidase (α-GLY) as a glycoside hydrolase class, which hydrolyzes the α-glycosidic bonds in the carbohydrate molecules, [17] breaks the α-1,4-linked terminals of a sugar moiety. Also, it helps in the breakdown of carbohydrate molecules.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, characterization, biological evaluation, and in silico studies of novel 1,3‐diaryltriazene‐substituted sulfathiazole derivatives

Işık

Akocak

Lolak

et al. 2020

Archiv der Pharmazie

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In the present study, a series of eleven novel 1,3‐diaryltriazene‐substituted sulfathiazole moieties (ST1–11) was synthesized by the reaction of diazonium salt of sulfathiazole with substituted aromatic amines and their chemical structures were characterized by Fourier transform infrared, 1H‐NMR (nuclear magnetic resonance), 13C‐NMR, and high‐resolution mass spectroscopy methods. These synthesized novel derivatives were found to be effective inhibitor molecules for α‐glycosidase (α‐GLY), human carbonic anhydrase (hCA), and acetylcholinesterase (AChE), with KI values in the range of 426.84 ± 58.42–708.61 ± 122.67 nM for α‐GLY, 450.37 ± 50.35–1,094.34 ± 111.37 nM for hCA I, 504.37 ± 57.22–1,205.36 ± 195.47 nM for hCA II, and 68.28 ± 10.26–193.74 ± 19.75 nM for AChE. Among the synthesized novel compounds, several lead compounds were investigated against the tested metabolic enzymes. More specifically, ST11 (4‐[3‐(perfluorophenyl)triaz‐1‐en‐1‐yl]‐N‐(thiazol‐2‐yl)benzenesulfonamide) showed a highly efficient inhibition profile against hCA I, hCA II, and AChE, with KI values of 450.37 ± 50.35, 504.37 ± 57.22, and 68.28 ± 10.26 nM, respectively. Due to its significant biological inhibitory potency, this derivative may be considered as an interesting lead compound against these enzymes.

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“…Clinical sulfonamides such as ethoxolamide, acetazolamide (AZA), dichlorphenamide, and methazolamide have been used as systemic CA inhibitors since 1950s. [ 46 ] Primary sulfonamides (RSO 2 NH 2 : R is an aromatic, aliphatic, or heterocyclic moiety) constitute a significant class of drugs comprising various pharmacological factors with anti‐CA activities. [ 47 ] In this study, among all synthetic novel benzimidazolium salts bearing 4‐hydroxyphenylethyl group 1a–e , complex 1c (hCA I, K i = 18.98 ± 3.57 µM; IC 50 = 21.85 µM with r 2 : 0.9989) having methyl group was recognized as the most potent inhibitor of hCA I isoform, when compared with the standard AZA ( K i = 60.51 ± 11.63 µM; Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…Clinical sulfonamides such as ethoxolamide, acetazolamide (AZA), dichlorphenamide, and methazolamide have been used as systemic CA inhibitors since 1950s. [46] Primary sulfonamides (RSO 2 NH 2 : R is an aromatic, aliphatic, or heterocyclic moiety) constitute a significant class of drugs comprising various pharmacological factors with anti-CA S C H E M E 1 Synthesis of the PEPPSI-Pd-NHC complexes (1a-e) bearing the 4-hydroxyphenylethyl group. PEPPSI-Pd-NHC, pyridine enhanced, precatalyst, preparation, stabilization, and initiation-Pd-N-heterocyclic carbene.…”

Section: Enzyme Inhibition Resultsmentioning

confidence: 99%

New PEPPSI‐Pd‐NHC complexes bearing 4‐hydroxyphenylethyl group: Synthesis, characterization, molecular docking, and bioactivity properties

Behçet

Taslimi

Gök

et al. 2022

Archiv der Pharmazie

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Five 4‐hydroxyphenylethyl substituted pyridine enhanced, precatalyst, preparation, stabilization, and initiation‐Pd‐N‐heterocyclic carbene (PEPPSI‐Pd‐NHC) complexes are synthesized in a straightforward way. All PEPPSI‐Pd‐NHC complexes were prepared by mixing 4‐hydroxyphenylethyl substituted NHC precursors, palladium chloride, potassium carbonate, and potassium bromide in pyridine. All complexes were screened for human carbonic anhydrase I (hCA I) and hCA II, acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and α‐glucosidase (α‐Glu) inhibitory activities. The ChE inhibitory activities of the new PEPPSI‐Pd‐NHC complexes bearing the 4‐hydroxyphenylethyl group (1a–e) against α‐Glu, AChE, and BChE were determined by the Tao and Ellman methods. The results indicated that all the synthetic complexes exhibited potent inhibitory activities against all targets as compared to the standard inhibitors, revealed by IC50 values. The Ki values of the new PEPPSI‐Pd‐NHC complexes 1a–e for hCA I, hCA II, AChE, BChE, and α‐Glu were obtained in the ranges of 18.98–32.65, 22.95–38.13, 3.67–11.65, 4.09–9.36, 186.92–287.45 µM, respectively. Among the synthesized complexes, the most potent complexes were 1c toward hCA I and II with Ki values 18.98 and 22.95 µM, and 1d toward AChE and BChE with Ki = 3.67 and 4.09 µM, respectively.

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Synthesis and investigation of anticancer, antibacterial activities and carbonic anhydrase, acetylcholinesterase inhibition profiles of novel (3aR,4S,7R,7aS)-2-[4-[1-acetyl-5-(aryl/heteroaryl)-4,5-dihydro-1H-pyrazol-3-yl]phenyl]-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-diones

Cited by 33 publications

References 83 publications

Pyrazoline Hybrids as Promising Anticancer Agents: An Up-to-Date Overview

Pyrazoline Hybrids as Promising Anticancer Agents: An Up-to-Date Overview

Synthesis, characterization, biological evaluation, and in silico studies of novel 1,3‐diaryltriazene‐substituted sulfathiazole derivatives

New PEPPSI‐Pd‐NHC complexes bearing 4‐hydroxyphenylethyl group: Synthesis, characterization, molecular docking, and bioactivity properties

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