Halogenated 1-(4-aminobenzylidene)indenes

Abstract

Notes stereochemistry of the heterocyclic derivatives at C-2 to be the same as the corresponding ketone, the hydrazines could have isomerized the methyl moiety during the condensation reaction. Use of semicarbazone or thiosemicarbazone resulted also in pyrazoles. All of the pyrazoles IIIa,c,d,f and VI exhibited uv maxima at 225-227 µ, which shifted to 231-235 µ in acidified alcohol. The phenylpyrazoles IIIb,e had a maximum at 253 µ, which was not affected by acidification. No attempt was made to ascertain the exact location of the phenyl ring.The pyrimidines IV were best prepared by melting an intimate mixture of the 1,3-diketones and guanidine carbonate or thiourea. Use of the standard baseor acid-catalyzed condensation conditions resulted only in the destruction or the recovery of diketone. The aminopyrimidines had double maxima of 230 and 303 µ, which could be shifted by acid to 226 and 312 µ, respectively. Thiourea product IVb had peaks at 233 and 286 µ.

Medicinal Chemistry of Indane and Its Analogues: A Mini Review

“…Notably, the presence of halogenated ortho substituent on aminobenzylidene ring lowered the anticancer potency of test compounds. Similarly, the replacement of 4‐NH 2 benzylidene ring system with cyclohexane, or the formation of Schiff base with 4‐NH 2 substituent at benzylidene ring diminished the anticancer activity [13] . These results suggested the importance of substituted 4‐NH 2 group on benzylidene substituent for an optimal activity.…”

Anticancer compounds. Further analogs of 1-(4-dimethylaminobenzylidene)indene

“…An amino group adjacent to the dimethylamino group was obtained by reduction of l-(3-nitro-4-7V,A/-dimethylaminobenzylidene)indene (8) to produce l-(3-amino-4-Ar,A/-dimethylaminobenzylidene)indene ( 9) which was inactive.…”