83254-84-6Relevant articles and documents
Structures and phase transition of three isomers of 1-phenylindolin-2-one derivatives: 6-chloro-1-phenylindolin-2-one, 4-chloro-1-phenylindolin-2-one and 1-(3-chlorophenyl)indolin-2-one
Wang, Bing,Fang, Qi
, p. 1750 - 1758 (2018/12/13)
Three 1-phenylindolin-2-one derivatives, namely 6-chloro-1-phenylindolin-2-one (A), 4-chloro-1-phenylindolin-2-one (B) and 1-(3-chlorophenyl)indolin-2-one (C), all C14H10ClNO, have been synthesized and the structures of these compounds at room temperature (ART, BRT and CRT) and low temperature (ALT, BLT and CLT) have been determined. Crystal A at 295 K (ART) crystallized in the monoclinic space group P21/c and the phenyl ring of the unique molecule exhibits disorder over two positions. At low temperature, the disorder disappeared and crystal A at 90 K (ALT) crystallized in the triclinic space group P with a doubled unit-cell volume and four molecules in the asymmetric unit. Density functional theory (DFT) calculations revealed a low oscillation barrier (0.24 kcal mol?1) of the phenyl ring of molecule A and the phase transition from the P21/c structure to the P structure can be interpreted in terms of the freezing out of the two conformations at low temperature. Crystal B retains space group P21/c in the temperature range from 100 to 297 K. A kind of obtuse-cell to acute-cell change can be recognized; if the unit cell of BLT at 100 K is set to be a standard obtuse cell [β = 90.341 (2)°] and the cell is kept untransformed in the course of temperature changing, the cell of BRT at 297 K was found to be acute [β = 89.288 (2)°]. The molecules in structure C are packed in layers, with C—H…O hydrogen bonds between neighbouring layers.
A Novel Class of "GABAergic" Agents: 1-Aryl-3-(aminoalkylidene)oxindoles
Sarges, Reinhard,Howard, Harry R.,Koe, B. Kenneth,Weissman, Albert
, p. 437 - 444 (2007/10/02)
Antagonism of mercaptopropionic acid (MPA) induced convulsions, reflecting a GABAergic mechanism, was observed in a series of 1-aryl-3-(aminoalkylidene)oxindoles.Optimal MPA antagonism was associated with 3-halo, 3-alkyl, and/or 4-alkoxy substituents in the pendant aryl ring and with (dimethylamino)methylene, 1-(dimethylamino)ethylidene and N-methyl-2-pyrrolidinylidene side chains.The precise mechanism of action of these agents is unclear at this time; however, they are not GABA mimics and they do not affect GABA levels.Like other GABAergic agents, these compounds are potent enhancers of benzodiazepine binding and they antagonize cyclic GMP elevations induced by isoniazid.Compounds from this series may therefore have potential therapeutic utility as anticonvulsants or anxiolytics.
