Design, Synthesis and Biological Evaluation of α-Aminophosphonate Derivatives Containing a Pyrazole Moiety

Abstract

Acetylcholinesterase (AChE) is a key enzyme which present in the central nervous system of living organisms. Organophosphorus pesticides (OPs) that serve as insecticides are AChE inhibitors which have been used widely in agriculture. A series of novel OPs containing pyrazole moiety have been designed and synthesized. The biological evaluation indicated compound 4e appeared 81% larvicidal activity against Plutella xylostella at the concentration of 0.1 mg/L and the inhibition of AChE by compound 4e was distinctly enhanced with the increasing doses. Molecular docking of compound 4e into the three dimensional X-ray structure of the Drosophila melanogaster AChE (DmAChE, PDB code: 1QO9) was carried out utilizating the Discovery Studio (DS), the binding model revealed that the title structure was tightly embedded in the binding sites of DmAChE. Therefore, we suggest that compound 4e may serve as a novel AChE inhibitor that can be utilized as a new insecticidal drug.

One‐pot synthesis, structure and structure–activity relationship of novel bioactive diphenyl/diethyl (3‐bromo‐1‐(3‐chloropyridin‐2‐yl)‐1H‐pyrazol‐5‐yl)(arylamino)methylphosphonates

“…For examples, α ‐aminophosphonate with pyrazole and benzene structural characteristics (Fig. , S ), reported by Cao et al recently, possesses promising insecticidal activity against Plutella xylostella at 0.1 mg L −1 concentration and AChE inhibitory activity . Thiadiazole‐containing α ‐aminophosphonates (Fig.…”

“…Moreover, α ‐aminophosphonates are an important class of bioactive compounds. Many α ‐aminophosphonate derivatives have been found to possess extensive biological potentials, such as anticancer, antimicrobial, antiviral, cytotoxic, antitumor, antifungal, insecticidal and herbicidal activities . For examples, α ‐aminophosphonate with pyrazole and benzene structural characteristics (Fig.…”

“…Many -aminophosphonate derivatives have been found to possess extensive biological potentials, such as anticancer, antimicrobial, antiviral, cytotoxic, antitumor, antifungal, insecticidal and herbicidal activities. [20][21][22][23][24][25][26][27][28][29][30][31][32] For examples, -aminophosphonate with pyrazole and benzene structural characteristics ( Fig. 2, S), reported by Cao et al recently, possesses promising insecticidal activity against Plutella xylostella at 0.1 mg L −1 concentration and AChE inhibitory activity.…”

“…2, S), reported by Cao et al recently, possesses promising insecticidal activity against Plutella xylostella at 0.1 mg L −1 concentration and AChE inhibitory activity. 28 Thiadiazole-containing -aminophosphonates ( Fig. 2, T and U) and chiral -aminophosphonate ( Fig.…”

Michael Cyclization of Polarized Systems: Synthesis and in vitro Anti-Diabetic Evaluation of Some Novel Pyrimidine, Pyridine, Pyrazole and Pyrazolo[3,4-b ]pyridine Derivatives

“…[20,21] Also, Pyrazoline derivatives widely occur in the environment, in the form of alkaloids, vitamins and pigments as constituents of plant and animal cell. Considerable attention has been carried out on the pyrazolines and substituted pyrazolines due to their inspiring biological activities such as antibacterial, antifungal, [22][23][24] antidepressant, [25][26][27][28] anticonvulsant, [29] and antitumor, [30] properties. The pyrazoline, a versatile moiety is present as the core constituent in a variety of leading drugs such as Sildenafil, Celebrex, and Rimonabant etc.…”