1559-45-1Relevant academic research and scientific papers
New geiparvarin analogues from 7-(2-oxoethoxy)coumarins as efficient in vitro antitumoral agents
Chimichi, Stefano,Boccalini, Marco,Cosimelli, Barbara,Viola, Giampietro,Vedaldi, Daniela,Dall'Acqua, Francesco
, p. 7473 - 7476 (2002)
A new class of compounds analogues of geiparvarin is described: aldolic condensation of 3(2H)-furanones and 7-(2-oxoethoxy)coumarins followed by a very efficient dehydration protocol led to the title compounds which show good antitumoral activity against several human cell lines.
New 5-(2-ethenylsubstituted)-3(2H)-furanones with in vitro antiproliferative activity
Chimichi, Stefano,Boccalini, Marco,Cosimelli, Barbara,Dall'Acqua, Francesco,Viola, Giampietro
, p. 5215 - 5223 (2007/10/03)
A convenient route to new 3(2H)-furanones is described through hydrogenolysis and subsequent acidic hydrolysis of isoxazoles. The antiproliferative activity of title compounds were evaluated against leukemia-, carcinoma-, neuroblastoma-, and sarcoma-derived human cell lines in comparison to the natural compound geiparvarin. The structure activity relationship indicated that the maximum in vitro antiproliferative activity correlates with the presence of a heterocyclic ring on the ethenyl moiety.
Synthesis and antiulcer activity of novel 5-(2-ethenyl substituted)-3(2H)- furanones
Felman,Jirkovsky,Memoli,Borella,Wells,Russell,Ward
, p. 1183 - 1190 (2007/10/02)
In order to investigate new antiulcer agents, spizofurone 1 (AG-629) was fragmented and reassembled to generate 5-phenyl-2,2-dimethyl-3(2H)-furanone (bullatenone, 2). Because of the antiulcer activity of 2,5-phenyl-substituted 2,2-dimethyl-3(2H)-furanones (3-6) were made and shown to have poor activity. Insertion of an ethenyl link between the furanone and phenyl rings gave 5-(2- phenylethenyl)-2,2-dimethyl-3(2H)-furanone (7). This compound had better activity than 2. Compounds 8-41 were synthesized to evaluate the SAR in 5-(2- ethenyl substituted)-3(2H)-furanones. Electron-withdrawing substituents on the aromatic ring (8, 10, 19, and 20) gave 2-3-fold higher activity. Further increases in the activity were found when the phenyl ring was replaced by heterocyclic nuclei. Compounds that contained a thiophene (29), pyridine (24- 26), or quinoline ring (32) had the best activity. Replacement of the methyl group on the furanone ring with a phenyl (34) or p-fluorophenyl (40) substituent in the 2-pyridine series gave compounds with activity that ranked with the best obtained in this study. The best compounds from the above SAR studies were evaluated in the ethanol-necrosis model for duration of cytoprotection action. Compounds 19, 24, and 29, which had the best duration of action, were tested with AG-629 in the acidified aspirin and indomethacin- induced lesion models. Only compound 24 had equivalent activity with AG-629 in both models.
REDUCTION OF Δ2-ISOXAZOLINES-2. A FACILE SYNTHESIS OF 3(2H)-FURANONES.
Curran, Dennis P.,Singleton, David H.
, p. 2079 - 2082 (2007/10/02)
A simple synthesis of the 3(2H)-furanone ring system is described.
NEW METHODS FOR THE SYNTHESIS OF 3(2H)-FURANONES AND 2(5H)-FURANONES.
Saimoto,Shinoda,Matsubara,Oshima,Hiyama,Nozaki
, p. 3088 - 3092 (2007/10/02)
New procedures for the synthesis of 3(2H)-furanones and 4-alkoxy-2(5H)-furanones are reported. Reaction of ketones with the lithium salt of propynal diethyl acetal, followed by treatment of the resulting 4-hydroxy-2-alkynal diethyl acetals with sulfuric a
Synthesis and Reactions of Simple 3(2H)-Furanones
Smith, Amos B.,Levenberg, Patricia A.,Jerris, Paula J.,Scarborough, Robert M.,Wovkulich, Peter M.
, p. 1501 - 1513 (2007/10/02)
Interest in the total synthesis of natural product antitumor agents which have as a central structural element the 3(2H)-furanone ring system has led to the development of an efficient general synthesis of a variety of simple 3(2H)-furanones.The strategy
