22118-95-2

Upstream product

• 591-51-5 phenyllithium 
• 5231-87-8 3,4-diethoxy-3-cyclobuten-1,2-dione 

Downstream Products

• 81467-38-1 4-(1,3-Dithian-2-yl)-3-ethoxy-4-hydroxy-2-phenylcyclobutenon 
• 118041-92-2 3-Ethoxy-4-hydroxy-2-phenyl-4-(3-phenyl-1-propynyl)-2-cyclobuten-1-one 
• 119908-13-3 3-ethoxy-4-hydroxy-2-phenyl-4-(1-phenylethenyl)-2-cyclobuten-1-one 
• 119908-15-5 3'-Ethoxy-[1,1';4',1'']terphenyl-2',5'-diol 
• 947703-11-9 3-(benzyl-pent-4-enyl-amino)-4-phenyl-cyclobut-3-ene-1,2-dione 
• 947703-06-2 3-[benzyl-(3-methyl-but-3-enyl)-amino]-4-phenyl-cyclobut-3-ene-1,2-dione 
• 947703-05-1 3-(benzyl-but-3-enyl-amino)-4-phenyl-cyclobut-3-ene-1,2-dione 
• 708-10-1 3-phenyl-4-hydroxycyclobut-3-ene-1,2-dione 
• 119908-14-4 3-ethoxy-4-hydroxy-2-phenyl-4-<(1-phenylmethyl)ethenyl>-2-cyclobuten-1-one 
• 124603-03-8 4-(1-n-butylethenyl)-3-ethoxy-4-hydroxy-2-phenyl-2-cyclobuten-1-one 

Relevant academic research and scientific papers

Triggering apoptosis in cancer cells with an analogue of cribrostatin 6 that elevates intracellular ROS

Elevation of reactive oxygen species (ROS) is both a consequence and driver of the upregulated metabolism and proliferation of transformed cells. The resulting increase in oxidative stress is postulated to saturate the cellular antioxidant machinery, leaving cancer cells susceptible to agents that further elevate their intracellular oxidative stress. Several small molecules, including the marine natural product cribrostatin 6, have been demonstrated to trigger apoptosis in cancer cells by increasing intracellular ROS. Here, we report the modular synthesis of a series of cribrostatin 6 derivatives, and assessment of their activity in a number of cell lines. We establish that placing a phenyl ring on carbon 8 of cribrostatin 6 leads to increased potency, and observe a window of selectivity towards cancer cells. The mechanism of activity of this more potent analogue is assessed and demonstrated to induce apoptosis in cancer cells by increasing ROS. Our results demonstrate the potential for targeting tumors with molecules that enhance intracellular oxidative stress.

Convergent synthesis of azabicycloalkenones using squaric acid as platform

The synthesis of azabicycloalkenones bearing a vinylogous amide moiety was achieved by means of the rhodium-catalyzed decarbonylative cycloaddition of cyclobutenediones with a pendant alkene. The starting cyclobutenediones were efficiently prepared from a

New synthesis of semisquaric acid derivatives via chlorinated N-(cyclobutylidene)amines

The synthesis and reactivity of new chlorinated AT-(cyclobutylidene)amines leading to new synthetic pathways toward various substituted cyclobutenediones is described.

Rearrangement of 4-Alkynylcyclobutenones. A New Synthesis of 1,4-Benzoquinones

A new convergent synthesis of 1,4-benzoquinones from 4-alkynyl-4-alkoxy(or hydroxy or trimethylsilyloxy)cyclobutenones is described.The required cyclobutenones are prepared from squaric acid and converted to the quinones upon mild thermolysis.The reaction proceeds via electrocyclic ring opening of the required cyclobutenones to (2-alkynylethenyl)ketenes, which then ring close to unique diradical intermediates.These then give the quinone products.The scope and mechanism of this unusual rearrangement are discussed.