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.
Highlights
Chalcones are 1,3-diaryl-2-propen-1-ones which belong to the flavonoid family [1,2,3]
Most techniques for the synthesis of deuterium-labeled compounds rely on expensive D2 gas as a deuterium source
To overcome the difficulties of conventional deuterium labeling techniques, we have developed a unique flow chemistry-based method for deuteration reactions by changing the hydrogen source to deuterated water in an H-Cube® system (Figure 3) [36,60,61]
Summary
Chalcones are 1,3-diaryl-2-propen-1-ones which belong to the flavonoid family [1,2,3]. Their naturally occurring representatives and synthetic analogs exert a wide array of pharmacological activities, including anticancer [4], antiviral [5], antibacterial [6], anti-inflammatory [7], antiplatelet [8] and antitubercular [9]. The metabolic syndrome and diabetes have become ever-increasing health issues worldwide [15]. The associated complications of these disorders, such as stroke, cardiovascular diseases, peripheral vascular diseases, diabetic neuropathy, renal failure, blindness and amputations, lead to reduced life expectancy, the enhancement of disability, and enormous medical costs [16,17,18]. Our research group has previously reported that certain synthetic chalcones (1-4) containing various halogen atoms at position 2 of ring A (Figure 2) effectively promote glucose
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