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

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°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.

Synthesis and Biological Activity of Some Bromophenols and Their Derivatives Including Natural Products

“…Based on their response to excess substrate, behavior in their environment, and sensitivity to inhibitors, they are classified into two groups. [20][21][22][23][24] AChE or true cholinesterase/acetylcholine acetylhydrolase and butyrylcholinesterase or pseudocholinesterase. Non-specific cholinesterase is also known as BChE or acylcholine acylhydrolase.…”

“…Cholinesterases are found in both cholinergic and non‐cholinergic tissues, as well as plasma and other bodily fluids. Based on their response to excess substrate, behavior in their environment, and sensitivity to inhibitors, they are classified into two groups [20–24] . AChE or true cholinesterase/acetylcholine acetylhydrolase and butyrylcholinesterase or pseudocholinesterase.…”

Biological activity and molecular docking studies of some N‐phenylsulfonamides against cholinesterases and carbonic anhydrase isoenzymes

“…In addition, their inhibition abilities were compared with standard compounds. On the other hand, as it is known, there are many computational studies on related target enzymes in the literature 52‐56 . Therefore, a molecular docking study for some strong candidates ( 9 , 10 , 11 , and 12 ) for the above‐mentioned targets is also performed in this research.…”

“…On the other hand, as it is known, there are many computational studies on related target enzymes in the literature. [52][53][54][55][56] Therefore, a molecular docking study for some strong candidates (9, 10, 11, and 12) for the above-mentioned targets is also performed in this research. As a result, the inhibition studies of the previously synthesized compounds against these enzymes and docking studies of some of them were carried out for the first time in this study.…”