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

9 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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