Microwave-assisted modified synthesis of C8-analogues of naturally occurring methylxanthines: Synthesis, biological evaluation and their practical applications
- Authors
- Shyamlal B.R.K.; Mathur M.; Yadav D.K.; Chaudhary S.
- Issue Date
- Jun-2020
- Publisher
- Elsevier B.V.
- Keywords
- Antioxidant; Antiplatelet; Cross-dehydrogenative coupling (CDC); Double C[sbnd]H bond activation; Microwave; TBHP
- Citation
- Fitoterapia, v.143
- Journal Title
- Fitoterapia
- Volume
- 143
- URI
- https://scholarworks.bwise.kr/gachon/handle/2020.sw.gachon/26431
- DOI
- 10.1016/j.fitote.2020.104533
- ISSN
- 0367-326X
- Abstract
- An efficient, microwave-assisted, oxidant-interceded, transition-metal-free, cross-dehydrogenative Csp 2-Csp 3 coupling of C8-Caffeine 2/Theobromine 3/theophylline 4 with substituted aliphatic alcohols 11a-l via C[sbnd]H bond activation for the preparation of series of substituted C8-(hydroxymethyl) Caffeine 12a-l/theobromine 13a-c/theophylline 14a-b has been developed using microwave irradiation upto 98% yield. The reaction proceeds smoothly in the presence of tert-butyl hydroperoxide (TBHP) under solvolysis condition at 120 °C for 20 min to corresponding substituted C8-(hydroxymethyl)-methylxanthine derivatives in good to excellent yields. The good substrate scope, control experiments, gram-scale synthesis, and practical synthetic transformations further highlights the practicality of this methodology. These C8-(hydroxymethyl) Caffeine 12a-l, 13a-c and 14a-b have been found to show promising in vitro antioxidant as well as antiplatelet activities. © 2020 Elsevier B.V.
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