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Issue 11, 2014
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Homologous 1,3,5-triarylpyrazolines: synthesis, CH⋯π interactions guided self-assembly and effect of alkyloxy chain length on DNA binding properties

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Abstract

A series of new 2-pyrazoline derivatives (1c–12c) bearing one to twelve carbon homologous alkyloxy side chains have been synthesized in good to excellent yields via intramolecular cyclization reaction on treatment of chalcone intermediates (1a–12a) with phenyl hydrazine (1b) and characterized on the basis of their physical and spectral (IR, 1H & 13C NMR, GC-MS) data. The solid state structure of compound (2c) showed intriguing and unique 1D-supramolecular zigzag chain-like self-assembled structure, the driving force of which is only CH⋯π interactions. DNA interaction studies have also been carried out on selected compounds 1c, 3c, 5c, 6c, 9c and 12c of the series by UV-visible spectroscopy to evaluate their anticancer potential and the effect of alkyloxy chain length on DNA binding property. All the tested compounds showed strong DNA binding (105–106 M−1 binding constants) with hyperchromic effect. A slight increase in the DNA binding strength, observed on increasing the chain length of alkyloxy groups, was attributed to their conformational arrangements, leading to the best fit conformation of 1,3,5-triaryl moiety in the minor groove of DNA structure.

Graphical abstract: Homologous 1,3,5-triarylpyrazolines: synthesis, CH⋯π interactions guided self-assembly and effect of alkyloxy chain length on DNA binding properties

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Supplementary files

Article information


Submitted
08 Jun 2014
Accepted
29 Aug 2014
First published
01 Sep 2014

New J. Chem., 2014,38, 5617-5625
Article type
Paper
Author version available

Homologous 1,3,5-triarylpyrazolines: synthesis, CH⋯π interactions guided self-assembly and effect of alkyloxy chain length on DNA binding properties

F. Anam, A. Abbas, K. M. Lo, Zia-ur-Rehman, S. Hameed and M. M. Naseer, New J. Chem., 2014, 38, 5617
DOI: 10.1039/C4NJ00938J

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