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Molecules 2016, 21(3), 318; doi:10.3390/molecules21030318

Continuous-Flow Synthesis of Deuterium-Labeled Antidiabetic Chalcones: Studies towards the Selective Deuteration of the Alkynone Core

1
Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary
2
MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, Eötvös u. 6, H-6720 Szeged, Hungary
3
Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan
4
School of Pharmacy, College of Pharmacy, China Medical University, Taichung 40402, Taiwan
5
Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 40447, Taiwan
6
Ph.D. Program in Toxicology and School of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan
7
Center for Infectious Disease and Cancer Research, Kaohsiung Medical University, Kaohsiung 807, Taiwan
*
Authors to whom correspondence should be addressed.
Academic Editor: Kerry Gilmore
Received: 9 February 2016 / Accepted: 24 February 2016 / Published: 7 March 2016
(This article belongs to the Special Issue Recent Advances in Flow Chemistry)
View Full-Text   |   Download PDF [1518 KB, uploaded 7 March 2016]   |  

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. View Full-Text
Keywords: chalcones; continuous-flow reactor; deuterium labeling; heterogeneous catalysis; triple bond reduction chalcones; continuous-flow reactor; deuterium labeling; heterogeneous catalysis; triple bond reduction
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MDPI and ACS Style

Ötvös, S.B.; Hsieh, C.-T.; Wu, Y.-C.; Li, J.-H.; Chang, F.-R.; Fülöp, F. Continuous-Flow Synthesis of Deuterium-Labeled Antidiabetic Chalcones: Studies towards the Selective Deuteration of the Alkynone Core. Molecules 2016, 21, 318.

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