33295-53-3

The compounds of the present invention are represented by the chemical structure found in Formula (I): wherein: the carbon atom designated * is in the R or S configuration; and X is a fused bicyclic carbocycle or heterocycle selected from the group consisting of benzofuranyl, benzo[b]thiophenyl, benzoisothiazolyl, benzoisoxazolyl, indazolyl, indolyl, isoindolyl, indolizinyl, benzoimidazolyl, benzooxazolyl, benzothiazolyl, benzotriazolyl, imidazo[1,2-a]pyridinyl, pyrazolo[1,5-a]pyridinyl, [1,2,4]triazolo[4,3-a]pyridinyl, thieno[2,3-b]pyridinyl, thieno[3,2-b]pyridinyl, 1H-pyrrolo[2,3-b]pyridinyl, indenyl, indanyl, dihydrobenzocycloheptenyl, tetrahydrobenzocycloheptenyl, dihydrobenzothiophenyl, dihydrobenzofuranyl, indolinyl, naphthyl, tetrahydronaphthyl, quinolinyl, isoquinolinyl, 4H-quinolizinyl, 9aH-quinolizinyl, quinazolinyl, cinnolinyl, phthalazinyl, quinoxalinyl, benzo[1,2,3]triazinyl, benzo[1,2,4]triazinyl, 2H-chromenyl, 4H-chromenyl, and a fused bicyclic carbocycle or fused bicyclic heterocycle optionally substituted with substituents (1 to 4 in number) as defined in R14; with R1, R2, R3, R4, R5, R6, R7, R8, and R14 defined herein.

The present invention provides compounds of formula (I): which are useful for treating depression, anxiety, and alleviating the symptoms caused by withdrawal or partial withdrawal from the use of tobacco or of nicotine.

Compounds of type A are fluorescent, if the donator groups, like NMe2, OMe, SMe and PR2, and the acceptor groups, like R'P(O)X, SO2R' and CO2R', are linked to different nuclei of the naphthalin ring system.The chemoselectivity of the electrophilic phosphoryl compounds P(O)X to nucleophiles like ROH, RNHR' and RSH is determined by the nature of the leaving group X responsible for different reaction mechanism.Phosphoryl groups with X = Cl attack predominantly R-NHR'- groups; phosphoryl compounds with X = F and OC6H4NO2(p) are ROH-selective.In this publication compounds of type A are presented, in which fluorescence and chemoselectivity are combined by structure in one molecule.These compounds are important analytic reagents (prove of the functional groups in the active site of enzymes) and as protective groups in the synthesis of natural products like peptides.