Continuous-flow synthesis of deuterium-labeled antidiabetic chalcones

Studies towards the selective deuteration of the alkynone core

Sándor B. Ötvös, Chi Ting Hsieh, Yang Chang Wu, Jih Heng Li, Fang Rong Chang, F. Fülöp, Kerry Gilmore

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Flow chemistry-based syntheses of deuterium-labeled analogs of important antidiabetic chalcones were achieved via highly controlled partial C≡C bond deuteration of the corresponding 1,3-diphenylalkynones. The benefits of a scalable continuous process in combination with on-demand electrolytic D2 gas generation were exploited to suppress undesired over-reactions and to maximize reaction rates simultaneously. The novel deuterium-containing chalcone derivatives may have interesting biological effects and improved metabolic properties as compared with the parent compounds.

Original languageEnglish
Article number318
JournalMolecules
Volume21
Issue number3
DOIs
Publication statusPublished - Mar 1 2016

Fingerprint

Chalcones
Deuterium
Hypoglycemic Agents
deuterium
Chalcone
biological effects
synthesis
Reaction rates
reaction kinetics
Gases
chemistry
analogs
Derivatives
gases

Keywords

  • Chalcones
  • Continuous-flow reactor
  • Deuterium labeling
  • Heterogeneous catalysis
  • Triple bond reduction

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Continuous-flow synthesis of deuterium-labeled antidiabetic chalcones : Studies towards the selective deuteration of the alkynone core. / Ötvös, Sándor B.; Hsieh, Chi Ting; Wu, Yang Chang; Li, Jih Heng; Chang, Fang Rong; Fülöp, F.; Gilmore, Kerry.

In: Molecules, Vol. 21, No. 3, 318, 01.03.2016.

Research output: Contribution to journalArticle

Ötvös, Sándor B. ; Hsieh, Chi Ting ; Wu, Yang Chang ; Li, Jih Heng ; Chang, Fang Rong ; Fülöp, F. ; Gilmore, Kerry. / Continuous-flow synthesis of deuterium-labeled antidiabetic chalcones : Studies towards the selective deuteration of the alkynone core. In: Molecules. 2016 ; Vol. 21, No. 3.
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