Article 2022 · 7 citations

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

Yavari, Mirali Akbar, Taslimi, Parham, Bayrak, Cetin, Taskin-Tok, Tugba, Menzek, Abdullah

Abstract

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 degrees 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, K-i values for acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and alpha-glucosidase (alpha-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 alpha-Gly enzymes in which important interactions were visualized and evaluated with residues of the binding region in each target enzyme.

Keywords

ALPHA-GLUCOSIDASE INHIBITORS CARBONIC-ANHYDRASE CRYSTAL-STRUCTURE ISOXAZOLE DERIVATIVES SWISS-MODEL ACETYLCHOLINESTERASE BUTYRYLCHOLINESTERASE ANTIOXIDANT THIOSEMICARBAZONE REARRANGEMENT

WoS Categories

Chemistry, Organic

Sustainable Development Goals

Good Health and Well-being

Citation

Journal: JOURNAL OF HETEROCYCLIC CHEMISTRY
Year: 2022
Volume: 59
Issue: 5
Pages: 864-878
ISSN: 0022-152X
eISSN: 1943-5193
DOI: 10.1002/jhet.4426
WoS UID: WOS:000734792400001

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