Synthesis, crystal structure and molecular docking studies of novel 2-(4-(4-substitutedphenylsulfonyl)piperazin-1-yl)quinolone-3-carbaldehyde derivatives

Nivedita, Rathnakar Desai and Gurunathan, Krishnaswamy and Suchetan, P. A. and Aruna Kumar, D. B. and Naveen, S. and Lokanath, N. K. and Sreenivasa, Swamy (2017) Synthesis, crystal structure and molecular docking studies of novel 2-(4-(4-substitutedphenylsulfonyl)piperazin-1-yl)quinolone-3-carbaldehyde derivatives. Research on Chemical Intermediates, 43 (11). pp. 6131-6154. ISSN 1568-5675

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Abstract

The present work reports the synthesis of novel 2-(4-(4-substitutedphenylsulfonyl) piperazin-1-yl) quinolone-3-carbaldehyde derivatives, namely, 2-(4-tosylpiperazin-1-yl)quinoline-3-carbaldehyde (4a), 2-(4-(4-nitrophenylsulfonyl)piperazin-1-yl)quinoline-3-carbaldehyde (4b) and 2-(4-(4-tert-butylphenylsulfonyl) piperazin-1-yl)quinoline-3-carbaldehyde (4c). These compounds have been characterized by FT-IR, 1H-NMR, 13C-NMR and LCMS. Further, the structures of compounds 4b and 4c have been elucidated by single crystal X-ray diffraction studies. The asymmetric unit of 4b contains two molecules (A and B) and that of 4c contains one. The piperazine ring in both the molecules 4b and 4c has chair conformation and the aldehyde group is twisted with respect to the quinoline group, respectively, by 13.3 (3)°, 18.2 (3)° and 11.2 (3)° in Molecule A & B of 4b and 4c due to the bulky piperazinyl group present in the ortho position. The crystal structures of both features interactions of the type C-HłdotsO, C-Hłdotsπaryl and πarylłdots πaryl, leading to a three-dimensional (3D) supramolecular architecture in 4b and a one-dimensional (1D) architecture in 4c. The various intermolecular interactions exhibited in 4b and 4c are well supported by Hirshfeld surface and fingerprint plots analysis. Further, the three compounds were evaluated for their in-silico antimicrobial activity. In-silico molecular docking studies were carried out in order to know the binding modes of the synthesized compounds with DNA Gyrase A and N-myristoyltranferase as target proteins for antibacterial and antifungal docking studies, respectively.

Item Type:	Article
Subjects:	C Chemical Science > Chemistry
Divisions:	Department of > Institution of Excellence Department of > Physics
Depositing User:	C Swapna Library Assistant
Date Deposited:	20 Jun 2019 05:33
Last Modified:	05 Jul 2019 09:22
URI:	http://eprints.uni-mysore.ac.in/id/eprint/3447

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