122762-89-4Relevant academic research and scientific papers
ONE-POT SYNTHESIS OF SUBSTITUTED CYCLOPROPENONE KETALS VIA ALKYLATION OF 3,3-DIALKOXY-2-SODIOCYCLOPROPENES
Isaka, Masahiko,Ando, Ryoichi,Morinaka, Yasuhiro,Nakamura, Eiichi
, p. 1339 - 1342 (1991)
A variety of substituted cyclopropenone ketals have been prepared by electrophilic trapping (protonolysis and alkylation) of sodium salts of cyclopropenone ketals that have been generated directly from the ketals of 1,3-dichloroacetone derivatives through cyclization with NaNH2 in a liq.NH3/ether mixture.
Peptidyl cyclopropenones: Reversible inhibitors, irreversible inhibitors, or substrates of cysteine proteases?
Cohen, Meital,Bretler, Uriel,Albeck, Amnon
, p. 788 - 799 (2013/09/02)
Peptidyl cyclopropenones were previously introduced as selective cysteine protease reversible inhibitors. In the present study we synthesized one such peptidyl cyclopropenone and investigated its interaction with papain, a prototype cysteine protease. A set of kinetics, biochemical, HPLC, MS, and 13C-NMR experiments revealed that the peptidyl cyclopropenone was an irreversible inhibitor of the enzyme, alkylating the catalytic cysteine. In parallel, this cyclopropenone also behaved as an alternative substrate of the enzyme, providing a product that was tentatively suggested to be either a spiroepoxy cyclopropanone or a gamma-lactone. Thus, a single family of compounds exhibits an unusual variety of activities, being reversible inhibitors, irreversible inhibitors and alternative substrates towards enzymes of the same family.
Pyridines from azabicyclo[3.2.0]hept-2-en-4-ones through a proposed azacyclopentadienone
Hemming, Karl,Khan, Musharraf N.,Kondakal, Vishnu V. R.,Pitard, Arnaud,Qamar, M. Ilyas,Rice, Craig R.
supporting information; experimental part, p. 126 - 129 (2012/02/16)
Pyridines have been formed by heating azabicyclo[3.2.0]hept-2-en-4-ones in toluene. The generation of a 3-azacyclopentadienone intermediate via a [2 + 2]-cycloreversion is proposed as the key step. A Diels-Alder reaction of a styrene, extrusion of carbon monoxide, and loss of hydrogen then gives the pyridine. The process parallels the well-known synthesis of benzenes from cyclopentadienones. The azabicyclo[3.2.0]hept-2-en-4-ones were synthesized from the reaction between readily available cyclopropenones and 1-azetines, in which the cyclopropenones behave as all-carbon 1,3-dipolar equivalents.
2-tert-Butoxy-3-phenylcyclopropanone acetal, a stable precursor of lithiated 2-phenylcyclopropenone acetal
Sakaki, Toshiro,Ando, Ryoichi
, p. 7011 - 7014 (2008/03/12)
2-tert-Butoxy-3-phenylcyclopropanone acetal 8 was found to be a stable precursor of lithiated cyclopropenone acetal. Acetal 8 was used in the practical synthesis of cysteine proteinase inhibitors; isolated yield of the key intermediate 14 was better than
GENERAL SYNTHESIS OF CYCLOPROPENONES AND THEIR ACETALS
Isaka, Masahiko,Ejiri, Satoshi,Nakamura, Eiichi
, p. 2045 - 2058 (2007/10/02)
Metalated cyclopropenone acetals 5 react with a variety of electrophiles, including alkyl halides, carbonyl compounds, vinyl iodides, vinyl triflates, and aryl iodides, to give substituted cyclopropenone acetals in high yield.Hydrolysis of the acetal unde
