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Total Synthesis and Anti-Inflammatory Evaluation of Osajin, Scandenone and Analogues.

ABSTRACT: In this study, the total synthesis of osajin, scandenone and their analogues have been accomplished. The key synthetic steps include aldol/intramolecular iodoetherification/elimination sequence reactions and a Suzuki coupling reaction to assemble the tricyclic core, chemoselective propargylation and Claisen rearrangement reactions to obtain natural compounds. In addition, we also designed and synthesized twenty-five natural product analogues. All synthetic compounds were screened for anti-inflammatory activity against tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6) in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophages. Collectively, Compound 39e and 39d were considered as promising lead compounds for further development.

SUBMITTER: Wang R

PROVIDER: S-EPMC10819276 | biostudies-literature | 2024 Jan

REPOSITORIES: biostudies-literature

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Total Synthesis and Anti-Inflammatory Evaluation of Osajin, Scandenone and Analogues.

Wang Rui R Ma Ran R Feng Ke K Lu Hongchen H Zhao Wei W Jin Hongzhen H

Pharmaceuticals (Basel, Switzerland) 20240109 1

In this study, the total synthesis of osajin, scandenone and their analogues have been accomplished. The key synthetic steps include aldol/intramolecular iodoetherification/elimination sequence reactions and a Suzuki coupling reaction to assemble the tricyclic core, chemoselective propargylation and Claisen rearrangement reactions to obtain natural compounds. In addition, we also designed and synthesized twenty-five natural product analogues. All synthetic compounds were screened for anti-inflam ...[more]

PMID: 38256918

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