754990-74-4

Basic information

• Product Name: C₁₇H₁₇NO₃
• Synonyms: C₁₇H₁₇NO₃
• CAS NO: 754990-74-4
• Molecular Weight: 283.327
• Mol File: 754990-74-4.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: C₁₇H₁₇NO₃(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₇H₁₇NO₃(754990-74-4)
• EPA Substance Registry System: C₁₇H₁₇NO₃(754990-74-4)

Safety Data

• Hazardous Substances Data: 754990-74-4(Hazardous Substances Data)

Upstream product

• 133613-71-5 (4R,5aS,7aS,7bR)-5,5a,6,7,7a,7b-hexahydro-7b-hydroxy-4-methyl-indeno[1,7-bc]furan-2(4H)-one 

Relevant articles and documents

Enantioselective syntheses and application of 4-: Epi -galiellalactone and the corresponding activity-based probe: From strained bicycles to strained tricycles

The [6,5,5] tricyclic fungal metabolite galiellalactone is a Michael acceptor that has been demonstrated to be a covalent inhibitor for Signal Transducer and Activator of Transcription 3 (STAT3). Recognizing the ring strain associated with the skeleton of this natural product, we utilized 1R-5S-bicyclo[3.1.0]hexan-2-one as the starting material and developed two novel approaches to accomplish the enantioselective total synthesis of the C4 epimer of galiellalactone in 5 and 7 steps, respectively, which capitalized on an efficient radical cyclization/fragmentation cascade reaction. Furthermore, an activity-based probe of 4-epi-galiellalactone with a terminal alkyne tag was successfully prepared to enable the experiments of activity-based protein profiling (ABPP). Through western blot and proteomic analysis, we not only confirmed the known target STAT3, but also identified a new target protein ataxin-7, which formed a covalent bond with the probe in intact cells via the Cys-129 residue.