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Vol. 33 No. 8 (2021): Vol 33 Issue 8, 2021

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Synthesis, Crystal Structure, Hirshfeld, DFT, Quorum Sensing Inhibition and Molecular Docking Studies of N'-{(E)-[3-(3,5-Difluorophenyl)1H-pyrazol-4-yl]methylidene}-4-methoxybenzohydrazide

https://doi.org/10.14233/ajchem.2021.23254%20
Vasantha Kumar
Department of P.G. Chemistry, Sri Dharmasthala Manjunatheshwara College (Autonomous), Ujire-574240, India
D. Ganavi
Department of Chemistry, Sri Dharmasthala Manjunatheshwara College (Autonomous), Ujire-574240, India; Department of Studies and Research in Chemistry, Mangalore University, Mangalagangotri-574199, India
B. Sukesh Kumar
Yenepoya Research Centre, Yenepoya (Deemed to be University), University Road, Mangalore-575018, India
Rajesh P. Shastry
Yenepoya Research Centre, Yenepoya (Deemed to be University), University Road, Mangalore-575018, India
A.H. Udaya Kumar
Department of Studies in Physics, University of Mysore, Manasagangotri, Mysuru-570006, India
S. Madan Kumar
IOE, University of Mysore, Manasagangotri, Mysuru-570 006, India
Mohammed Al-Ghorbani
Department of Chemistry, Thamar University, Dhamar, Yemen; Department of Chemistry, Science and Arts College, Ulla, Taibah University, Madinah, Saudi Arabia
P.M. Gurubasavaraja Swamy
Department of Pharmaceutical Chemistry, Acharya & B.M. Reddy College of Pharmacy, Soldevanahalli, Bangalore-560107, India
N.K. Lokanath
Department of Studies in Physics, University of Mysore, Manasagangotri, Mysuru-570006, India
K. Naveen
Department of P.G. Chemistry, Sri Dharmasthala Manjunatheshwara College (Autonomous), Ujire-574240, India
Boja Poojary
Department of Studies and Research in Chemistry, Mangalore University, Mangalagangotri-574199, India

Corresponding Author(s) : Vasantha Kumar

vasantha.kumar1886@gmail.com

Asian Journal of Chemistry, Vol. 33 No. 8 (2021): Vol 33 Issue 8, 2021

Abstract

In present study, the synthesis, structural, quorum sensing inhibition and computational studies of a new N’-{(E)-[3-(3,5-difluorophenyl)-1H-pyrazol-4-yl]methylidene}-4-methoxybenzohydrazide are reported. The structure of the synthesized compound was confirmed by IR, 1H & 13C NMR and mass spectral data. The single crystals of the compound was obtained using ethanol as a crystallization solvent. The synthesized compound (C40H40N8O6F4) crystallizes in the monoclinic crystal system, C2/c space group. Various intermolecular interactions were quantified using a 3D molecular Hirshfeld surface computational method. The 2D fingerprint plots revealed that the H···H (35.9%) interactions have a major contribution to the total molecular surface. DFT studies was performed to establish the molecular crystal structure of the compound and to study the HOMO-LUMO energies of the compound. The anti-quorum sensing study of the target compound on Chromobacterium violaceum (wild type) biosensor revealed that quorum quenching activity at 300 μg/mL. Interestingly, quantitative assay exhibited more than 80% of quorum sensing inhibition without interfering cell growth (p < 0.05). Molecular docking studies of the compound on CviR protein (PDB: 3QP8) confirmed the observed activity through strong hydrogen bonding interaction with the amino acids in the binding pocket.

Keywords

Pyrazole Hydrazone Crystal study Hirshfeld study Quorum sensing inhibition Molecular docking studies
Kumar, V., Ganavi, D., Sukesh Kumar, B., P. Shastry, R., Udaya Kumar, A., Madan Kumar, S., … Poojary, B. (2021). Synthesis, Crystal Structure, Hirshfeld, DFT, Quorum Sensing Inhibition and Molecular Docking Studies of N’-{(E)-[3-(3,5-Difluorophenyl)1H-pyrazol-4-yl]methylidene}-4-methoxybenzohydrazide. Asian Journal of Chemistry, 33(8), 1796–1804. https://doi.org/10.14233/ajchem.2021.23254
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