title: Continuous-Flow Synthesis of Deuterium-Labeled Antidiabetic Chalcones: Studies towards the Selective Deuteration of the Alkynone Core.
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.
authors.affiliation: Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary. otvossandor@pharm.u-szeged.hu.|MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, Eötvös u. 6, H-6720 Szeged, Hungary. otvossandor@pharm.u-szeged.hu.
authors.forename: Sándor B
authors.initials: SB
authors.lastname: Ötvös
authors.affiliation: Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary. u98831001@gmail.com.|Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan. u98831001@gmail.com.
authors.forename: Chi-Ting
authors.initials: CT
authors.lastname: Hsieh
authors.affiliation: School of Pharmacy, College of Pharmacy, China Medical University, Taichung 40402, Taiwan. yachwu@mail.cmu.edu.tw.|Chinese Medicine Research and Development Center, China Medical University Hospital, Taichung 40447, Taiwan. yachwu@mail.cmu.edu.tw.
authors.forename: Yang-Chang
authors.initials: YC
authors.lastname: Wu
authors.affiliation: Ph.D. Program in Toxicology and School of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan. jhlitox@kmu.edu.tw.
authors.forename: Jih-Heng
authors.initials: JH
authors.lastname: Li
authors.affiliation: Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung 807, Taiwan. aaronfrc@kmu.edu.tw.|Center for Infectious Disease and Cancer Research, Kaohsiung Medical University, Kaohsiung 807, Taiwan. aaronfrc@kmu.edu.tw.
authors.forename: Fang-Rong
authors.initials: FR
authors.lastname: Chang
authors.affiliation: Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary. fulop@pharm.u-szeged.hu.|MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, Eötvös u. 6, H-6720 Szeged, Hungary. fulop@pharm.u-szeged.hu.
authors.forename: Ferenc
authors.initials: F
authors.lastname: Fülöp
mesh_terms: D002384:Catalysis; D047188:Chalcones / Q000138:chemical synthesis* / Q000737:chemistry; D060326:Chemistry Techniques, Synthetic; D003903:Deuterium / Q000737:chemistry*; D007004:Hypoglycemic Agents / Q000138:chemical synthesis* / Q000737:chemistry; D007553:Isotope Labeling
chemical_list: D047188:Chalcones; D007004:Hypoglycemic Agents; D003903:Deuterium
keywords: chalcones; continuous-flow reactor; deuterium labeling; heterogeneous catalysis; triple bond reduction