Inhibition of acetylcholinesterase by two arylderivatives: 3a-Acetoxy-5H-pyrrolo(1,2-a) (3,1)benzoxazin-1,5-(3aH)-dione and cis-N-p-Acetoxy-phenylisomaleimide

José Correa-Basurto, Judith Espinosa-Raya, Mario González-May, L. Michel Espinoza-Fonseca, Iván Vázquez-Alcántara, José Trujillo-Ferrara

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

Abstract

Two arylderivatives, 3a-Acetoxy-5H-pyrrolo(1,2-a) (3,1)benzoxazin-1,5-(3aH)-dione 3 and cis-N-p-Acetoxy-phenylisomaleimide 4, were synthesized from anthranilic acid and para-aminophenol, respectively. The inhibitory effects of these compounds on acetylcholinesterase (AChE) activity were evaluated in vitro as well as by docking simulations. Both compounds showed inhibition of AChE activity (Ki = 4.72 ± 2.3 μM for 3 and 3.6 ± 1.8 μM for 4) in in vitro studies. Moreover, they behaved as irreversible inhibitors and made π-π interaction with W84 and hydrogen bonded with S200 and Y337 according to experimental data and docking calculations. The docking calculations showed ΔG bind (kcal/mol) of -9.22 for 3 and -8.58 for 4. These two compounds that can be use as leads for a new family of anti-Alzheimer disease drugs.

Original languageEnglish (US)
Pages (from-to)133-138
Number of pages6
JournalJournal of Enzyme Inhibition and Medicinal Chemistry
Volume21
Issue number2
DOIs
StatePublished - Apr 2006

Bibliographical note

Funding Information:
We are grateful to CONACyT and COFAA and SIP-IPN for scholarships and financial support to the Authors. L.M.E.F’s research is supported by grants from the Department of Biochemistry, Structural Biology and Biophysics, and the Minnesota Supercomputing Institute, University of Minnesota, USA.

Keywords

  • AChE
  • Acetylcholinesterase
  • Alzheimer
  • Anilines
  • Arylderivatives
  • Docking
  • Inhibitors

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