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

Author(s): Eslam S. Daldoom, Malak I. Qadri, Jalal A. Zahra, Salim S. Sabri, Mustafa M. El-Abadelah, Monther A. Khanfar, Sanaa Bardaweel, Wolfgang Voelter*

Journal Name: Letters in Organic Chemistry

Volume 18 , Issue 1 , 2021


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Graphical Abstract:


Abstract:

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.

Keywords: 5-Aminoindane, Japp-Klingemann reaction, hydrazonoyl chlorides, amidrazones, N-(substituted)piperazines.

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Article Details

VOLUME: 18
ISSUE: 1
Year: 2021
Published on: 18 August, 2020
Page: [41 - 48]
Pages: 8
DOI: 10.2174/1570178617999200818210315
Price: $65

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