847440-49-7

Usage

Uses

Used in Pharmaceutical Industry:
O-(Methylthio)Methyl Triptolide is used as a key intermediate in the synthesis of D-ring-modified triptolide analogues. These analogues are of significant interest due to their potential therapeutic applications, particularly in the development of novel drugs targeting various diseases and conditions.
In the context of drug discovery and development, O-(Methylthio)Methyl Triptolide plays a crucial role in the preparation of triptolide derivatives with improved pharmacological profiles. The D-ring modification can lead to enhanced efficacy, reduced toxicity, and better pharmacokinetic properties, making these analogues more suitable for clinical use.
Overall, O-(Methylthio)Methyl Triptolide is a valuable compound in the pharmaceutical industry, serving as a building block for the creation of innovative and effective therapeutic agents derived from the Triptolide family.

Upstream product

• 38748-32-2 triptolide 
• 108-24-7 acetic anhydride 
• 67-68-5 dimethyl sulfoxide 
• 75-18-3 dimethylsulfide 

Downstream Products

• 847440-52-2 C₃₆H₃₆O₈S 
• 1254702-92-5 14-O-phosphonooxymethyltriptolide dibenzyl ester 

Relevant academic research and scientific papers

Total synthesis of novel D-ring-modified triptolide analogues: Structure-cytotoxic activity relationship studies on the D-ring of triptolide

The total synthesis of a trans-position butenolide analogue of triptolide 3 and the semi-synthesis of analogue 4, with a furan ring, and compound 5, without a planar D-ring, are described. Studies into the antitumor activity of these compounds suggest that the five-membered unsaturated lactone ring (D-ring) of triptolide is essential to its potent anticancer activity and the C18 carbonyl group may exert an important influence on the interaction between triptolide and the target molecule(s) responsible for initiating their cytotoxic effects.

METHODS TO TREAT FIBROSIS, NASH, AND NAFLD

The invention provides a method for treating fibrosis, nonalcoholic fatty liver disease (NAFLD) or nonalcoholic steatohepatitis (NASH) in an animal, comprising administering to the animal, a compound of formula I: or a pharmaceutically acceptable salt thereof.

Design, synthesis and structure-activity relationships studies on the d ring of the natural product triptolide

Triptolide is a diterpene triepoxide natural product isolated from Tripterygium wilfordii Hook F, a traditional Chinese medicinal herb. Triptolide has previously been shown to possess antitumor, anti-inflammatory, immunosuppressive, and antifertility activities. Earlier reports suggested that the five-membered unsaturated lactone ring (D ring) is essential for potent cytotoxicity, however, to the best of our knowledge, systematic structure- activity relationship studies have not yet been reported. Here, four types of D ring-modified triptolide analogues were designed, synthesized and evaluated against human ovarian (SKOV-3) and prostate (PC-3) carcinoma cell lines. The results suggest that the D ring is essential to potency, however it can be modified, for example to C18 hydrogen bond acceptor and/or donor furan ring analogues, without complete loss of cytotoxic activity. Interestingly, evaluation of the key series of C19 analogues showed that this site is exquisitely sensitive to polarity. Together, these results will guide further optimization of this natural product lead compound for the development of potent and potentially clinically useful triptolide analogues.

TRIPTOLIDE PRODRUGS

The invention provides compounds of formula (I): or a salt thereof. The invention also provides pharmaceutical compositions comprising a compound of formula I, processes for preparing compounds of formula I, intermediates useful for preparing compounds of formula I and therapeutic methods using the compounds of formula I.

Tripolide Lactone Ring Derivatives as Immunomodulators and Anticancer Agents

Disclosed are compounds based on lactone ring modifications of triptolide and hydroxylated triptolide, for use in therapy, such as antiproliferative, anticancer, and immunosuppressive therapy.

METHOD FOR TREATMENT OF INFLAMMATORY DISORDERS USING TRIPTOLIDE COMPOUNDS

Inflammatory disorders, including obliterative airway disease, renal fibrosis, diabetic nephropathy, and liver fibrosis are treated with immunosuppressive triptolide compounds, in particular triptolide compounds effective to inhibit TGF-β production in a patient afflicted with such a disorder.