Synthesis and rearrangement reactions of 1,4-dihydrospiro[1,4-methanonaphthalene-9,1′-cyclopropane] derivatives

Bayrak, Cetin; Şenol, Halil; Sirtbasi, Sedef; Şahin, Ertan; Menzek, Abdullah

doi:10.1016/j.tet.2018.07.060

Cited by 15 publications

(4 citation statements)

References 29 publications

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“…The data that support the findings of this study are available in the supplementary material of this article. Additional references cited within the Supporting Information [42,43] …”

Section: Supporting Information Summarymentioning

confidence: 99%

Celecoxib Derivatives Containing Pyrazole Linked‐Sulfonamide Moiety: Carbonic Anhydrase I–II and Acetylcholinesterase Inhibition Profiles, Molecular Docking Studies

et al. 2023

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Heterocyclic pyrazole compounds have cytotoxic, anticancer, antimicrobial, anti‐inflammatory properties, as well as their derivatives containing sulfonamide moiety, show superior effects on inhibiting various enzymes. Pre‐synthesized celecoxib‐derived compounds were studied for their inhibitory effects on human carbonic anhydrase (hCA I and hCA II) isoforms and acetylcholinesterase (AChE). The compound containing 2,3 dimethoxyphenyl functional groups from the celecoxib derivative containing this sulfonamide moiety showed a strong inhibitory effect with Ki values at 21.70±2.50 nM, 4.70±2.20 nM, and 4.58±0.80 nM for hCA I, hCA II, and AChE, respectively. In addition, these compounds were evaluated against acetazolamide (AZA) and tacrine (TAC), which are used as standard inhibitors for the studied enzymes. The compound obtained as a result of the reaction of pyrazole compounds with propionic anhydride and showing the best inhibition effect had higher inhibitory activity than the standard inhibitors we used. In addition, molecular docking analyses to the strongest inhibitor were performed to identify possible binding mechanisms with the active sites of all three enzymes. Based on both in vitro and molecular docking analysis results, this compound was determined as a potential inhibitor of AChE, hCA I, and hCA II isoenzymes.

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“…The data that support the findings of this study are available in the supplementary material of this article. Additional references cited within the Supporting Information [42,43] …”

Section: Supporting Information Summarymentioning

confidence: 99%

Celecoxib Derivatives Containing Pyrazole Linked‐Sulfonamide Moiety: Carbonic Anhydrase I–II and Acetylcholinesterase Inhibition Profiles, Molecular Docking Studies

et al. 2023

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“…Values such as melting point (Mp), elemental analysis, infrared (IR) spectra, and nuclear magnetic resonance (NMR) (varian (300 and 400 MHz) in spectrometers) spectra used in the characterization of all compounds were obtained as previously described. [3,24] All column chromatography (on silica gel [60 Mesh; Merck]) and preparative thick-layer chromatography (with 1 mm of silica gel 60 PF [Merck] on glass plates) was used. High resolution mass spectroscopy (HRMS) data were obtained by liquid chromatography-mass spectroscopy-time of flight electrospray ionization (1200/6210, Agilent).…”

Section: Chemistrymentioning

confidence: 99%

“…Pyramidalized alkenes such as benzonorbornadiene react with reagents such as bromine and diene from exo face because the electron density is higher in this face. [3,[14][15][16][17][18][19][20][21][22][23][24] If the exo approach of the reagents to alkenes is hindered due to the steric effect, products formed by the endo approach can be obtained. [64,65] In addition, the exo-syn approach of the reagents to these alkenes is unfavorable due to the steric effect.…”

Section: Chemistrymentioning

confidence: 99%

“…Therefore, configurations of the adducts 6a-h and 9a-d should be exo-anti. These configurations are determined by some methods such as X-ray analysis [3,16,23,24] and "W" interaction. [3,14,66] The bridge hydrogen in the direction of the benzene ring should resonate in the higher field in 1 H-NMR due to the benzene ring and should interact "W" with the hydrogens in the five-membered ring.…”

Section: Chemistrymentioning

confidence: 99%

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Synthesis and some enzyme inhibition effects of isoxazoline and pyrazoline derivatives including benzonorbornene unit

Yavari

Adiloglu

Kaya

et al. 2021

J Biochem & Molecular Tox

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Four new and four known isoxazoline derivatives were synthesized from the reactions of benzonorbornadiene with nitrile oxides formed from the corresponding benzaldehydes. Three new and one known pyrazoline derivatives were also synthesized from the reactions of the benzonorbornadiene with nitrile imines formed from the corresponding compounds. The synthesized nitrogenbased novel heterocyclic compounds were evaluated against the human carbonic anhydrase isoenzymes I and II (hCA I and hCA II), acetylcholinesterase (AChE), and butyrylcholinesterase (BChE) enzymes. The synthesized nitrogenbased novel heterocyclic compounds showed IC 50 values in the range of 2.69-7.01 against hCA I, 2.40-4.59 against hCA II, 0.81-1.32 µM against AChE, and 20.83-1.70 µM against BChE enzymes. On the contrary, nitrogen-based novel heterocyclic compounds demonstrated K i values between2.93 ± 0.59-8.61 ± 1.39 against hCA I, 2.05 ± 0.62-4.97 ± 0.95 against hCA II, 0.34 ± 0.02-0.92 ± 0.17 nM against AChE, and 0.50 ± 0.04-1.20 ± 0.16 µM against BChE enzymes. The synthesized nitrogen-based novel heterocyclic compounds exhibited effective inhibition profiles against both indicated metabolic enzymes. These results may contribute to the development of new drugs particularly to treat some disorders, which are widespread in the world including glaucoma and Alzheimer's diseases.

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Synthesis of nitrogen-containing oleanolic acid derivatives as carbonic anhydrase and acetylcholinesterase inhibitors

et al. 2023

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Synthesis and rearrangement reactions of 1,4-dihydrospiro[1,4-methanonaphthalene-9,1′-cyclopropane] derivatives

Cited by 15 publications

References 29 publications

Celecoxib Derivatives Containing Pyrazole Linked‐Sulfonamide Moiety: Carbonic Anhydrase I–II and Acetylcholinesterase Inhibition Profiles, Molecular Docking Studies

Celecoxib Derivatives Containing Pyrazole Linked‐Sulfonamide Moiety: Carbonic Anhydrase I–II and Acetylcholinesterase Inhibition Profiles, Molecular Docking Studies

Synthesis and some enzyme inhibition effects of isoxazoline and pyrazoline derivatives including benzonorbornene unit

Synthesis of nitrogen-containing oleanolic acid derivatives as carbonic anhydrase and acetylcholinesterase inhibitors

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