Pinacolborane-assisted superacid organocatalysis enabled direct access to cytotoxic alkyl N-Cbz aminesopen access
- Authors
- Kim, Woo Hee; Song, Seon Bin; Lee, Da Eun; Goswami, Prithwish; Chung, You Kyoung; Choi, Sohyeong; Jung, Won Hee; Choi, Sang Un; Ham, Shinwon; Oh, Yujin; Kim, Ki Hyun; Huh, Joonsuk; Bae, Han Yong
- Issue Date
- 21-Feb-2024
- Publisher
- Cell Press
- Keywords
- bioactivity evaluation; Cbz-amine; hydroboration; organocatalysis; reductive amination; super Brønsted acid
- Citation
- Cell Reports Physical Science, v.5, no.2
- Indexed
- SCIE
SCOPUS
- Journal Title
- Cell Reports Physical Science
- Volume
- 5
- Number
- 2
- URI
- https://scholarworks.bwise.kr/skku/handle/2021.sw.skku/110182
- DOI
- 10.1016/j.xcrp.2024.101786
- ISSN
- 2666-3864
2666-3864
- Abstract
- α-Secondary alkyl amines are structural motifs frequently encountered in a wide variety of natural products and pharmaceuticals. The N-benzyloxycarbonyl (Cbz) compound is a widely used precursor, acknowledged for its efficacy in implementing a masked amine strategy to access a privileged moiety. Although reductive amination is conducted as a crucial portion of the pharmaceutical industry, direct catalytic access to alkyl Cbz-amine is still rare due to the low reactivity of carbamate. Here, we show a superacid organocatalyst enabled direct access to bioactive Cbz-protected α-secondary alkyl amines using general ketones as the starting material. Through the highly selective and robust catalytic process, a wide substrate scope including drug precursor scaffolds in preparative scalability (up to >99% yield) with practical pharmaceutical syntheses is achieved. The obtained N-Cbz products are found to possess strong cytotoxicities in in vitro bioactivity evaluations, indicating their potential as promising candidates for new anticancer drug discovery. © 2024 The Author(s)
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- Appears in
Collections - Pharmacy > Department of Pharmacy > 1. Journal Articles
- Graduate School > Chemistry > 1. Journal Articles
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