138958-56-2

Upstream product

• 55086-61-8 5-acetyl-3-methylisoxazole 
• 71502-43-7 (3-methyl-5-isoxazolyl)-1-ethanol 
• 127-66-2 2-Phenyl-3-butyn-2-ol 
• 79-24-3 Nitroethane 
• 5780-37-0 (E)-acetaldoxime 

Downstream Products

• 138958-50-6 4-[(E)-2-(5-Methyl-4-oxo-5-phenyl-4,5-dihydro-furan-2-yl)-vinyl]-benzonitrile 
• 138958-46-0 2-methyl-2-phenyl-5-[2-(2-pyridinyl)ethenyl]-3(2H)-furanone 
• 138958-48-2 2-Methyl-2-phenyl-5-((E)-2-pyridin-4-yl-vinyl)-furan-3-one 
• 138958-47-1 2-phenyl-2-methyl-5-[2-(3-pyridinyl)ethenyl]-3(2H)-furanone 
• 138958-49-3 (E)-2-methyl-2-phenyl-5-[2-(thien-3-yl)ethenyl]-3(2H)-furanone 
• 133255-53-5 2,5-dimethyl-2-phenyl-3(2H)-furanone 

Relevant academic research and scientific papers

New 5-(2-ethenylsubstituted)-3(2H)-furanones with in vitro antiproliferative activity

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

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.