5586-73-2Relevant articles and documents
Reactions of 3-arylpropenenitriles with arenes under superelectrophilic activation conditions: Hydroarylation of the carbon-carbon double bond followed by cyclization into 3-arylindanones
Gorbunova, Yelizaveta,Zakusilo, Dmitriy N.,Boyarskaya, Irina A.,Vasilyev, Aleksander V.
, (2020/05/25)
Reactions of 3-arylpropenenitriles [ArCH[dbnd]CHCN] with arenes [Ar'H] under the superelectrophilic activation conditions with Br?nsted superacid TfOH (CF3SO3H) or strong Lewis acid AlBr3 result, first, in the formation of products of hydroarylation of the carbon-carbon double bond, 3,3-diarylpropanenitriles [Ar(Ar’)CHCH2CN]. Reactions may go further in TfOH leading to 3-arylindanones, as products of intramolecular aromatic acylation by the electrophilically activated nitrile group. Intermediate cationic species, derived at the protonation of the starting 3-arylpropenenitriles onto the carbon of C[dbnd]C bond and the nitrile nitrogen, have been studied by DFT calculation. A plausible reaction mechanism including the formation of highly reactive dications [(Ar)HC+–CH2C+ = NH] has been proposed. The obtained 3,3-diarylpropanenitriles have been transformed into pharmaceutically valuable 5-(2,2-diarylethyl)-1H-tetrazoles [Ar(Ar’)CHCH2Tetr] and 3-diarylpropylamines [Ar(Ar’)CH(CH2)2NH2] by the reactions with NaN3 and LiAlH4 correspondingly.
CYCLIC ETHER COMPOUNDS AS SODIUM CHANNEL MODULATORS
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, (2008/06/13)
A compound of the formula: wherein R 1 and R 2 each represents hydrogen, lower alkyl which may be substituted or acyl; R 3, R 4 and R 5 each represents lower alkyl which may be substituted or lower alkoxy which may be substituted or R 4 and R 5 taken together represent a 5-or 6-membered carbocyclic group; R 6 represents lower alkyl; Ar represents an aromatic group which may be substituted; ring A represents a 5-to 8-membered nitrogen-containing heterocyclic ring which may be substituted; X represents lower alkylene which may be substituted; Y represents carbon or nitrogen; Za represents CH 2, COCH 2, OCH 2, SCH 2, NHCH 2, etc.; Zb represents a bond or a divalent aliphatic hydrocarbon group which may be substituted and may contain O, N or S; and m represents an integer of 1 to 3, or a salt thereof is useful for a pharmaceutical composition for modulating sodium channel.
Synthesis and pharmacological study of diphenylalkylamines with cycloaliphatic residues; new coronary vasodilators
Carenini,Carissimi,Gentili,Grumelli,Picciola,Ravenna
, p. 2127 - 2136 (2007/10/06)
The paper describes the synthesis and the pharmacological evaluation of some derivatives of prenylamine, all with a cycloaliphatic ring within or instead of the isopropylamine moiety. Where the alicyclic ring had a bulky substituent in para were more active than prenylamine as coronary vasodilators on isolated guinea pig heart (Langendorff). The most interesting derivative was MG 8926 [N (3,3 diphenylpropyl) α methyl β cyclohexylethylamine], which was more active than prenylamine on Langendorff's heart and in enhancing the pressor response to catecholamines and inhibiting the isoprenaline induced hypotension. Moreover, it had almost the same effects as prenylamine as spasmolytic, local and general anesthetic, on heart rate and arterial pressure and against coronary spasm from pitressin.