- Facile synthesis of 3(2H)-furanones
-
Abstract: A practical method for the synthesis of 3(2H)-furanones including the bullatenone was described. Intramolecular cyclization of 4-hydroxyalkynones in the presence of KOH affords the biologically potent furanones in moderate-to-good yield at room temperature. Synthesis of 4-hydroxyalkynones from the reaction of acid chloride and terminal alkyne in the presence of copper iodide at room temperature was also reported.
- Panda, Niranjan,Nayak, Dinesh K.
-
p. 1093 - 1100
(2018/02/22)
-
- 1, 2 DISUBSTITUTED HETEROCYCLIC COMPOUNDS
-
1,2-disubstituted heterocyclic compounds which are inhibitors of phosphodiesterase 10 are described. Also described are processes, pharmaceutical compositions, pharmaceutical preparations and pharmaceutical use of the compounds in the treatment of mammals, including human(s) for central nervous system (CNS) disorders and other disorders which may affect CNS function. Among the disorders which may be treated are neurological, neurodegenerative and psychiatric disorders including, but not limited to, those associated with cognitive deficits or schizophrenic symptoms.
- -
-
-
- 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.
- Felman,Jirkovsky,Memoli,Borella,Wells,Russell,Ward
-
p. 1183 - 1190
(2007/10/02)
-
- A Novel and Practical Synthetic Method of 3(2H)-Furanone Derivatives
-
A novel convenient synthetic method of 5-aryl-2,2-dimethyl-3(2H)-furanones (aryl = C6H5, 2-CH3C6H4, 3-CH3C6H4, 4-CH3C6H4, 2-ClC6H4, 4-ClC6H4, 2,4-Cl2C6H3) is described.It involves the Claisen-Schmidt condensation (potassium hydroxide/ethanol) of aromatic
- Sakai, Takashi,Yamawaki, Akitoshi,Ito, Hiroshi,Utaka, Masanori,Takeda, Akira
-
p. 1199 - 1201
(2007/10/02)
-