Synthesis, molecular modeling and BACE-1 inhibitory study of tetrahydrobenzo[b] pyran derivatives

Vijaya Bhaskar, Reshma Chowdary, Sheshagiri R. Dixit, Shrinivas D. Joshi

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

β-Secretase (BACE1) has been broadly documented as one of the possible therapeutic targets for the treatment of Alzheimer's disease. In this paper, we report the synthesis and the for β-secretase (BACE-1) inhibitory activity of new series of tetrahydrobenzo [b] pyran derivatives. One-pot synthesis of tetrahydrobenzo [b] pyrans was carried out by condensing aromatic aldehyde, malononitrile and 1,3-cyclohexanedione using ionic liquid 1-butyl-3-methyl imidazolium chloride ([bmIm]Cl ) in aqueous alcohol media. The addition of alcohol and water in the ratio of 1:2 keeps all the reactants in solution which facilitates the reaction and makes the product formation very easy. The synthesized compounds were subjected to BACE1 inhibition assay and six compounds, 4d, 4e, 4f, 4h, 4i, and 4p have shown significant IC 50 values at micromolar level. Among these six active compounds, 4e was a potential inhibitor with its IC 50 value in nanomolar range. All the synthesized compounds were docked onto the active site of β-Secretase enzyme.

Original languageEnglish
Pages (from-to)202-210
Number of pages9
JournalBioorganic Chemistry
Volume84
DOIs
Publication statusPublished - 01-03-2019
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry

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