Modified heteroarotinoids as potential anticancer agents—improved syntheses of 2-nitrotetralin and 2-aminotetralin

Abstract EN

series of modified heteroarotinoids were prepared.

Methods to obtain systems with closed ring units and with open chains have been developed.

Heteroarotinoids with a thiourea or urea linking group between two aryl rings comprise the major structures.

A group of amino-substituted arenes were condensed with 4-nitrophenylisocyanate or 4-nitrophenylisothiocyanate in extremely dry THF under N2 at 0 ?C, the resulting mixtures being left a room temperature with stirring for 24 h.

Flash chromatography or one simple recrystallization afforded solids with an average yield of 65.5% for 16 compounds.

Both spectral and elemental analysis supported each structure.

Synthetic methodology to obtain somewhat rare intermediates 2-nitrotetralin and 2-aminotetralin in a consistent manner are reported.

The modified heteroarotinoids have potential as agents to treat ovarian cancer