1361940-76-2

Upstream product

• 1240580-55-5 C₁₈H₁₉NO₄ 
• 106-53-6 para-bromobenzenethiol 
• 1361940-59-1 C₂₄H₂₄BrNO₄S 
• 108-24-7 acetic anhydride 
• 6080-33-7 Sinomenine Hydrochloride 

Relevant academic research and scientific papers

Regio- and stereoselective C10β-H functionalization of sinomenine: An access to more potent immunomodulating derivatives

Regio- and stereoselective C10β-H functionalization of sinomenine, an economically available natural immunomodulating alkaloid, has been studied, developed and successfully applied to the synthesis of new immunosuppressive sinomenine derivatives in a protecting-free fashion. Regioselective oxidation of sinomenine with (diacetoxyiodo)benzene (DIB) in water provided a single stable benzoquinone derivative 4, and subsequent 1,6-conjugated addition of 4 with alcohols, amines, and thiols afforded a new series of C10β-H functionalized sinomenine derivatives stereoselectively. Some derivatives with a newly introduced 10β- bezenesulfanyl substituent exhibited much higher TNF-α inhibitory potency than their natural parent sinomenine. This work opens a convenient access to novel sinomenine derivatives with medicinal interests.

SINOMENINE DERIVATIVES, SYNTHETIC METHODS AND USES THEREOF

The invention relates to sinomenine derivatives, methods for their synthesis and their applications. The sinomenine derivatives include oxidation derivatives, and C-10 substituted sinomenine derivatives. Based on the readily oxidizable phenol group on sinomenine structure, using oxidation, oxidative dearomatization, or conjugated addition aromatization, one can introduce C-10 substitutions to synthesize the sinomenine derivatives. The sinomenine derivatives of the invention have the following structures: Using in vitro TNF-α inhibition assay, the activities of the synthetic compounds are assessed. Results from these assays shown that most compounds have anti-inflammatory effects, and some compounds have better activities than that of sinomenine. These compounds may be used in treating immune diseases such as rheumatoid arthritis (RA).