Re-revision of the Stereo Structure of Piperidine Lactone, an Intermediate in the Synthesis of Febrifugine

Takeuchi, Yasuo; Azuma, Kumiko; Abe, Hitoshi; Sasaki, Kenji; Harayama, Takashi

doi:10.1248/cpb.50.1011

Cited by 8 publications

(1 citation statement)

References 28 publications

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“…Some of the early synthesis procedures encountered various problems because of uncertainty regarding the absolute stereochemistry. It was found that under certain conditions febrifugine and isofebrifugine could interconvert [29]. Recently, an elegant review was published that described the chemical complexity of the molecules involved and the problems encountered during the synthesis of febrifugine, isofebrifugine and halofuginone [30].…”

Section: The Origin Of Halofuginone and Its Synthesismentioning

confidence: 99%

Halofuginone — The Multifaceted Molecule

2015

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Abstract:Halofuginone is an analog of febrifugine-an alkaloid originally isolated from the plant Dichroa febrifuga. During recent years, halofuginone has attracted much attention because of its wide range of beneficial biological activities, which encompass malaria, cancer, and fibrosis-related and autoimmune diseases. At present two modes of halofuginone actions have been described: (1) Inhibition of Smad3 phosphorylation downstream of the TGFβ signaling pathway results in inhibition of fibroblasts-to-myofibroblasts transition and fibrosis. (2) Inhibition of prolyl-tRNA synthetase (ProRS) activity in the blood stage of malaria and inhibition of Th17 cell differentiation thereby inhibiting inflammation and the autoimmune reaction by activation of the amino acid starvation and integrated stress responses. This review deals with the history and origin of this natural product, its synthesis, its known modes of action, and it's various biological activities in pre-clinical animal models and in humans.

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Section: The Origin Of Halofuginone and Its Synthesismentioning

confidence: 99%

Halofuginone — The Multifaceted Molecule

2015

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Stereoselective Intermolecular [4+2] Process of N,O‐acetals with Terminal Alkynes for Construction of Functional cis‐Pyrido and Pyrrolo[1,2‐c][1,3]oxazin‐1‐ones

et al. 2019

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