Nadeem, A. and Hamdi Hamid, S. and Fares Hezam, Al-Ostoot and Hussien Ahmed, K. and Sultan A., Al-horaibi and Sridhar, M. A. and Shaukath Ara Khanum and Mahendra, M. and Mohamed, El Hafi and Joel, T. M. and El Mokhtar, E. and Youssef, R. (2021) Synthesis, crystal structure, DFT calculations, Hirshfeld surface analysis, energy frameworks, molecular dynamics and docking studies of novel isoxazolequinoxaline derivative (IZQ) as anti-cancer drug. Journal of Molecular Structure, 1232.
Full text not available from this repository. (Request a copy)Abstract
Quinoxaline derivatives with the molecular formula C8H6N2] also named benzopyrazines, which are a valuable class of heterocyclic compounds useful for their numerous industrial and pharmaceutical applications. The new isoxazolquinoxalin (IZQ) 3-pheny1-14(3-(p-toly1)-4,5-dihydroisoxazol-5yl)methyl)quinoxalin-2(1H)- one (5) has been synthesized with good yield by stirring the compounds of 1-allyl-3-phenylquinoxalin-2(1H)-one (3, 3.8mmol), and (E)-4 methylbenzaldehydeoxime (4, 1.3mmol) in 20 ml of chloroform. The aqueous solution of sodium hypochlorite (10 ml of water bleach 12 degrees) was added drop wise using bromine funnel. The mixture was stirring at 0 degrees C temperature for 6 hours. Then it dried to obtain a crude product which on recrystallization with ethanol afforded the title compound (5) as colourless rectangular block shape crystals, and then confirmed by H NMR, LC-MS spectra. The structure of the compound has been confirmed by single crystal X-ray diffraction technique. The compound crystallizes in the monoclinic crystal system with the space group P2(1)/c. The unit cell constants; a =15.9437(6) angstrom, b =16.3936(6) angstrom, c =7.4913(3) angstrom, and beta =94.178(2)degrees. DFT calculations were carried out and HOMO-LUMO energy levels have been determined. In the structure, both Intermolecular and intramolecular hydrogen bonds of the type C-H center dot center dot center dot O were observed along with C-H center dot center dot center dot cg interactions. Hirshfeld surface studies were performed to understand the different interaction contacts of the molecule and the molecular packing strength of the crystal. Energy frameworks were constructed through different intermolecular interaction energies to investigate the stability of the compound and to know type of the dominate energy. Docking studies predicted anti-cancer activity of the title molecule against homo sapiens protein (pdb code:6HVH) and exhibited prominent interactions at active site region. (C) 2021 Elsevier B.V. All rights reserved.
| Item Type: | Article |
|---|---|
| Uncontrolled Keywords: | Isoxazolquinoxaline (IZQ); Crystal structure; DFT calculations; Energy frameworks; Docking study; Anti-cancer |
| Subjects: | D Physical Science > Physics |
| Divisions: | Department of > Physics |
| Depositing User: | Mr Umendra uom |
| Date Deposited: | 23 May 2022 10:18 |
| Last Modified: | 18 Nov 2022 10:39 |
| URI: | http://eprints.uni-mysore.ac.in/id/eprint/17227 |
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