Synthesis and Properties of N1-(indan-5-yl)amidrazones Incorporating Piperazines and Related Congeners

A selected set of new N1-(indan-5-yl)amidrazones 4a-p, encompassing piperazines or related amines, has been prepared via interaction of the hydrazonoyl chloride 3 (derived from 5-aminoindane) with the appropriate sec-cyclic amine in the presence of triethylamine. Their suggested structures are supported by IR, ¹H NMR, ¹³C NMR, high-resolution MS (ESI) spectral data, and further confirmed by single-crystal X-ray crystallography for 4k. These novel compounds were screened for their antitumor activity against breast cancer cells (MCF7 and T47D); amongst all of them, only compound 4o, incorporating N-(pyrimidin-2-yl)piperazine, was fairly active with IC50 values of 69 μM and 61 μM, respectively.