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Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
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Acetophenone Monomers from Acronychia trifoliolata.

Katsunori Miyake1, Airi Suzuki1, Chihiro Morita1

  • 1School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University , Kanazawa, 920-1192, Japan.

Journal of Natural Products
|November 1, 2016
PubMed
Summary

Seven new acronyculatins (1-7) and four known acetophenone monomers were isolated from Acronychia trifoliolata. Acronyculatins I and J exhibited moderate antiproliferative activity against cancer cell lines.

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Area of Science:

  • Natural Product Chemistry
  • Phytochemistry
  • Medicinal Chemistry

Background:

  • Acronychia trifoliolata is a plant source of bioactive compounds.
  • Acetophenone monomers are a class of natural products with diverse biological activities.

Purpose of the Study:

  • To isolate and characterize novel compounds from Acronychia trifoliolata.
  • To evaluate the antiproliferative activity of isolated compounds against human cancer cell lines.

Main Methods:

  • Extraction of plant material using methanol/dichloromethane.
  • Structure elucidation using Nuclear Magnetic Resonance (NMR) and High-Resolution Mass Spectrometry (HRMS).
  • Assessment of antiproliferative activity using cancer cell line assays.

Main Results:

  • Isolation of seven new acronyculatins (1-7) and four known acetophenone monomers.
  • Revision of the structure of acronyculatin B (8).
  • Acronyculatins I (1) and J (2) demonstrated moderate antiproliferative activity.

Conclusions:

  • Acronychia trifoliolata yields structurally diverse acetophenone monomers.
  • Acronyculatins I and J represent potential leads for anticancer drug development.