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- W4386851063 abstract "Abstract The pharmacokinetics of pharmaceutical drugs can be improved by replacing C−H bonds with the more stable C−D bonds at the α‐position to heteroatoms, which is a typical metabolic site for cytochrome P450 enzymes. However, the application of deuterated synthons is limited. Herein, we established a novel concept for preparing deuterated reagents for the successful synthesis of complex drug skeletons with deuterium atoms at the α‐position to heteroatoms. ( d n ‐Alkyl)diphenylsulfonium salts prepared from the corresponding nondeuterated forms using inexpensive and abundant D 2 O as the deuterium source with a base, were used as electrophilic alkylating reagents. Additionally, these deuterated sulfonium salts were efficiently transformed into d n ‐alkyl halides and a d n ‐alkyl azide as coupling reagents and a d n ‐alkyl amine as a nucleophile. Furthermore, liver microsomal metabolism studies revealed deuterium kinetic isotope effects (KIE) in 7‐( d 2 ‐ethoxy)flavone. The present concept for the synthesis of deuterated reagents and the first demonstration of a KIE in a d 2 ‐ethoxy group will contribute to drug discovery research based on deuterium chemistry." @default.
- W4386851063 created "2023-09-20" @default.
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- W4386851063 date "2023-09-27" @default.
- W4386851063 modified "2023-09-29" @default.
- W4386851063 title "Alkyl Sulfonium Salt‐based Reagents for Introduction of Deuterated Alkyl Groups in Drug Discovery" @default.
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- W4386851063 doi "https://doi.org/10.1002/ange.202311058" @default.
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