Cycloaddition Reactions of Benzonorbornadiene and Homonorbornadiene: New Isoxazoline and Pyridazine Derivatives

Adiloglu, Yadigar; Şahin, Ertan; Tutar, Ahmet; Menzek, Abdullah

doi:10.1002/jhet.3229

Cited by 6 publications

(15 citation statements)

References 38 publications

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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%

“…Known compounds 6a-d were synthesized according to the literature. [3] (3aS*,4S*,9S*,9aS*)-3-(p-Tolyl)-3a,4,9,9a-tetrahydro-4,9methanonaphtho [2,3-d]…”

Section: General Procedures For 13-dipolar Cycloaddition Reaction Of ...mentioning

confidence: 99%

“…According to known methods, benzonorbornadiene (4) and aldoximes 6a-d were synthesized and purified. [3,63] By one-pot reaction method, all the nitrile oxides using intermediate were synthesized from the reactions of corresponding aldoximes 5a-h and NaOCl. Benzonorbornadiene (4) was reacted with each aldoxime in the presence of NaOCl between at low temperatures [−6 ± 4°C] and RT in approximately 15 h (Scheme 1).…”

Section: Chemistrymentioning

confidence: 99%

“…According to the NMR spectra of these adducts 6a-h, their structures are consistent with the proposed structures. Known [3] four adducts 6a-d and four new adducts 6e-h were obtained from these reactions (Scheme 1).…”

Section: Chemistrymentioning

confidence: 99%

“…As shown in the text, these adducts should be obtained by exo-cycloaddition of intermediate nitrile imine to 4 because of exo selectivity. [3,[14][15][16][17] Hydrogens in the five-membered rings resonated in the range of 4.55-3.88 ppm as d (J = 9.4 or 9.2 Hz).…”

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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Section: Chemistrymentioning

confidence: 99%

“…Known compounds 6a-d were synthesized according to the literature. [3] (3aS*,4S*,9S*,9aS*)-3-(p-Tolyl)-3a,4,9,9a-tetrahydro-4,9methanonaphtho [2,3-d]…”

Section: General Procedures For 13-dipolar Cycloaddition Reaction Of ...mentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

See 3 more Smart Citations

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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Chemical Constituents from Sargassum fusiforme (Harv.) Setch.

Wang

Xiang

Huang

et al. 2020

Chemistry & Biodiversity

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Phytochemical investigation of Sargassum fusiforme (Harv.) Setch. led to the discovery of fifteen secondary metabolites, including three sterols, three monoterpenes, five nitrogenous compounds, two fatty acids, and two others. Among them, two compounds are new, while the other thirteen compounds were isolated from S. fusiforme for the first time. The structures of the two new compounds were identified by NMR and HR‐ESI‐MS data analyses, and the absolute configurations were established by comparing the calculated and experimental ECD spectroscopic data.

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1,3‐dipolar cycloaddition reactions of the compound obtaining from cyclopentadiene‐PTAD and biological activities of adducts formed selectively

Yavari

Taslimi

Bayrak

et al. 2021

Journal of Heterocyclic Chem

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After known adduct (4) was synthesized by cycloaddition reaction of cyclopentadiene with 4‐phenyl‐1,2,4‐triazoline‐3,5‐dione, seven new isoxazoline derivatives were synthesized from reactions of 4 with corresponding oximes prepared from benzaldehyde derivatives in the existence of the aqueous NaOCl in CH2Cl2 at 0°C—RT via nitrile oxides. Four new pyrazoline derivatives were also synthesized from reactions of 4 with corresponding prepared reagents via nitrile imines. Selectively, each of all isoxazole and pyrazoline derivatives was synthesized by 1,3‐dipolar cycloaddition reactions of compound 4 with the corresponding reagents. Based on the results of their biological activity analyses, Ki values for acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and alpha‐glucosidase (α‐Gly) enzymes were obtained in this range 32.15 ± 5.73–107.44 ± 19.52 22.57 ± 4.30–186.07 ± 23.51, and 69.08 ± 8.54–528.07 ± 38.46 nM, respectively. Besides that, these compounds were subjected to molecular docking to describe the interaction against AChE, BChE, and α‐Gly enzymes in which important interactions were visualized and evaluated with residues of the binding region in each target enzyme.

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Cycloaddition Reactions of Benzonorbornadiene and Homonorbornadiene: New Isoxazoline and Pyridazine Derivatives

Cited by 6 publications

References 38 publications

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

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

Chemical Constituents from Sargassum fusiforme (Harv.) Setch.

1,3‐dipolar cycloaddition reactions of the compound obtaining from cyclopentadiene‐PTAD and biological activities of adducts formed selectively

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