74285-86-2

Usage

Uses

Used in Pharmaceutical Industry:
Triptophenolide is used as an anti-cancer agent for its ability to inhibit the growth of various cancer cell lines, including breast, lung, and colon cancer cells, by inducing cell cycle arrest and apoptosis.
Used in Anti-inflammatory Applications:
Triptophenolide is used as an anti-inflammatory agent for its potential to inhibit the production of pro-inflammatory cytokines, thereby reducing inflammation.
Used in Antiparasitic Drug Development:
Triptophenolide is used as a potential drug candidate for the treatment of neglected tropical diseases such as trypanosomiasis and leishmaniasis, due to its antiparasitic activity against the causative agents of these diseases.
Overall, Triptophenolide's diverse biological activities make it a valuable target for further research and potential development into new drugs for various medical applications.

InChI:InChI=1/C20H24O3/c1-11(2)12-4-6-16-14(18(12)21)5-7-17-15-10-23-19(22)13(15)8-9-20(16,17)3/h4,6,11,17,21H,5,7-10H2,1-3H3/t17-,20+/m0/s1

Upstream product

• 238746-43-5 (4aS,10aR)-7-Isopropyl-8-methoxy-4a-methyl-2-trifluoromethanesulfonyloxy-3,4,4a,9,10,10a-hexahydro-phenanthrene-1-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 238746-44-6 Trifluoro-methanesulfonic acid (4aS,10aR)-1-hydroxymethyl-7-isopropyl-8-methoxy-4a-methyl-3,4,4a,9,10,10a-hexahydro-phenanthren-2-yl ester 
• 238746-42-4 (1S,4aS,10aS)-7-Isopropyl-8-methoxy-4a-methyl-2-oxo-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene-1-carboxylic acid (1S,2R,5S)-5-methyl-2-(1-methyl-1-phenyl-ethyl)-cyclohexyl ester 
• 74311-48-1 (3bR,9bS)-7-isopropyl-6-methoxy-9b-methyl-3b,4,5,9b,10,11-hexahydrophenanthro[2,1-c]furan-1(3H)-one 

Downstream Products

• 163513-81-3 11,14-dioxo-19-(4->3)-abeo-abieta-3,8,12-trien-19,18-olide 

Relevant academic research and scientific papers

Enantioselective Total Synthesis of (-)-Triptolide, (-)-Triptonide, (+)-Triptophenolide, and (+)-Triptoquinonide

The first enantioselective total synthesis of (-)-triptolide (1), (-)-triptonide (2), (+)-triptophenolide (3), and (+)-triptoquinonide (4) was completed. The key step involves lanthanide triflate-catalyzed oxidative radical cyclization of (+)-8-phenylmenthyl ester 30 mediated by Mn(OAc)9, providing intermediate 31 with good chemical yield (77%) and excellent diastereoselectivity (dr 38:1). (+)-Triptophenolide methyl ether (5) was then prepared in >99% enantiomeric excess (>99% ee), and readily converted to natural products 1-4. In addition, transition state models were proposed to explain the opposite chiral induction observed in the oxidative radical cyclization reactions of chiral β-keto esters 17 (without an α-substituent) and 17a (with an α-chloro substituent).