DABCO-PEG ionic liquid catalyzed synthesis, single-crystal structure, and antioxidant activity of a flavanone derivative
Source abstract
Abstract
Globally, the occurrence of skin cancers has been increasing day by day due to unprotected skin and exposure to UV radiation. This research is focused toward the evaluation of the antioxidant potential of an OH-free flavanone derivative that was synthesized by using 1,4-diazabicyclo[2.2.2]octane–polyethylene glycol (DABCO-PEG) 400. Ionic liquid was prepared via the alkylation of DABCO using 1-pentyl bromide followed by mixing with PEG 400. The structure of the synthesized molecules was characterized through single-crystal XRD. The target flavanone, viz., 2-(4-isobutylphenyl)chroman-4-one, was subjected to free radical activity. In addition, in silico studies were carried out with proteins ribonucleotide reductase and tyrosinase and isobutyl containing flavanone, viz., 2-(4-isobutylphenyl)chroman-4-one. The flavanone 2-(4-isobutylphenyl)chroman-4-one showed significant inhibition at a concentration of 25 μg/ml compared to vitamin C, which was also supported by the molecular docking studies. The flavanones exhibit binding energies of −6.45 and −6.83 kcal/mol for ribonucleotide reductase and tyrosinase, respectively. The results were further validated by molecular dynamic simulations, which recommended that further investigation of this flavanone must be carried out before using it in potent drug discovery in the field of skin cancer.
Source: crossref · Quality: baseline
Research context
OpenAlex topics: Ionic liquids properties and applications · Oxidative Organic Chemistry Reactions · Multicomponent Synthesis of Heterocycles
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
Affiliations
Department of Pharmaceutical Chemistry, Faculty of Pharmacy, The Islamia University of Bahawalpur 1 , Bahawalpur 63100, Pakistan
Department of Chemistry, University of Azad Jammu and Kashmir 2 , Muzaffarabad 13100, Pakistan
Department of Basic Sciences and Humanities, Faculty of Information Science and Humanities, Dawood University of Engineering and Technology 3 , Karachi 74800, Pakistan
Department of Chemistry, University of Gujrat 4 , Gujrat 50700, Pakistan
Department of Chemistry, Quaid-i-Azam University 5 , 45320 Islamabad, Pakistan
Department of Homoeopathic Medical Sciences, Faculty of Medicine and Allied Health Sciences, The Islamia University of Bahawalpur 6 , Bahawalpur, Pakistan
Department of Chemistry, University of Karachi 7 , Karachi 75270, Pakistan
Dr. M. A. Kazi Institute of Chemistry, University of Sindh 8 , Jamshoro, Pakistan
Department of Physics, Faculty of Science and Humanities, Shaqra University 9 , Ad-Dawadimi 11911, P.O. Box 1040, Shaqra, Saudi Arabia
Department of Chemistry, Government College Women University 10 , Sialkot 51300, Pakistan
Department of Physics, Faculty of Engineering, Hacettepe University 11 , Beytepe, Ankara 06800, Türkiye
References (39)
Show source-provided references
1. Deep eutectic solvents formed between choline chloride and carboxylic acids: Versatile alternatives to ionic liquids10.1021/ja048266j ↗
2. SIRPOW.92—A program for automatic solution of crystal structures by direct methods optimized for powder data10.1107/S002188989400021X ↗
3. Synthesis of imidazolium and pyridinium-based ionic liquids and application of 1-alkyl-3-methylimidazolium salts as pre-catalysts for the benzoin condensation using solvent-free and microwave activation10.1016/J.TET.2009.11.110 ↗
4. Therapeutic potential of standardized extract of Melilotus indicus (L.) all. And its phytochemicals against skin cancer in animal model: In vitro, in vivo, and in silico studies10.1021/acsomega.2c03053 ↗
5. Patterns in hydrogen bonding: Functionality and graph set analysis in crystals10.1002/anie.199515551 ↗
6. Acetophenone-based 3,4-dihydropyrimidine-2(1H)-thione as potential inhibitor of tyrosinase and ribonucleotide reductase: Facile synthesis, crystal structure, in-vitro and in-silico investigations10.3390/ijms232113164 ↗
7. DBU derived ionic liquids and their application in organic synthetic reactions
8. Ionic liquids: A brief history10.1007/s12551-018-0419-2 ↗
9. Statistical analysis on the performance of molecular mechanics Poisson–Boltzmann surface area versus absolute binding free energy calculations: Bromodomains as a case study10.1021/acs.jcim.7b00347 ↗
10. Ultraviolet A radiation exposure and melanoma: A review10.1097/CMR.0000000000000857 ↗
11. 2010
12. Low-transition-temperature mixtures (LTTMs): A new generation of designer solvents10.1002/anie.201207548 ↗
13. Mutual solubilities of water and hydrophobic ionic liquids10.1021/jp076271e ↗
14. Room-temperature ionic liquids: Solvents for synthesis and catalysis. 210.1021/cr1003248 ↗
15. Organic synthesis in deep eutectic solvents: Paal–Knorr reactions10.1016/j.tetlet.2013.05.122 ↗
16. Imidazolium-based ionic liquids catalyzed formylation of amines using carbon dioxide and phenylsilane at room temperature10.1021/acscatal.5b01274 ↗
17. Quantitative analysis of intermolecular interactions in orthorhombic rubrene10.1107/S2052252515012130 ↗
18. Silica bonded n-propyl-4-aza-1-azoniabicyclo[2.2.2]octane chloride (SB-DABCO): A highly efficient, reusable and new heterogeneous catalyst for the synthesis of 4H-benzo[b]pyran derivatives10.1016/j.apcata.2011.04.012 ↗
19. Bonded-atom fragments for describing molecular charge densities10.1007/BF00549096 ↗
20. Inhibitors of the cancer target ribonucleotide reductase, past and present10.3390/biom12060815 ↗
21. TONTO–A system for computational chemistry
22. Preparation and applications of room temperature ionic liquids in organic synthesis: A review on recent efforts10.2174/2213346101666140915212515 ↗
23. Iodine catalyzed one-pot synthesis of flavanone and tetrahydropyrimidine derivatives via Mannich type reaction10.1016/j.tet.2011.11.022 ↗
24. Silica tethered Pd–DABCO complex: An efficient and reusable catalyst for Suzuki–Miyaura reaction10.1007/s10562-012-0912-3 ↗
25. A new multipurpose diffractometer PILATUS @ SNBL10.1107/S1600577516002411 ↗
26. SIRPOW.92—A program for automatic solution of crystal structures by direct methods optimized for powder data10.1107/S0021889894000221 ↗
27. WinGX and ORTEP for windows: An update10.1107/S0021889812029111 ↗
28. ORTEP-3 for Windows—A version of ORTEP-III with a graphical user interface (GUI)10.1107/S0021889897003117 ↗
29. Polymer-supported DABCO–palladium complex as a stable and reusable catalyst for room temperature Suzuki–Miyaura cross-couplings of aryl bromides10.1016/j.tetlet.2006.10.148 ↗
30. A mild and convenient synthesis of quinoxalines via cyclization–oxidation process using DABCO as catalyst10.1016/j.tetlet.2010.01.107 ↗
31. Physical properties and intermolecular interaction of eutectic solvents binary mixtures: Reline and ethaline10.1002/apj.1978 ↗
32. Applications of ionic liquids in the chemical industry10.1039/B006677J ↗
33. Skin cancer disease detection using transfer learning technique10.3390/app12115714 ↗
34. Synthesis of dendrimers terminated by DABCO ligands and applications of its palladium nanoparticles for catalyzing Suzuki–Miyaura and Mizoroki–Heck couplings10.1002/aoc.2930 ↗
35. Hirshfeld surface analysis10.1039/B818330A ↗
36. Crystal structure, Hirshfeld surfaces and DFT computation of NLO active (2E)-2-(ethoxycarbonyl)-3-[(1-methoxy-1-oxo-3-phenylpropan-2-yl)amino] prop-2-enoic acid10.1016/j.saa.2015.09.002 ↗
37. Electrostatic potentials mapped on Hirshfeld surfaces provide direct insight into intermolecular interactions in crystals10.1039/B715227B ↗
38. (E)-2,6-Dibromo-4-{2-[1-(1H, 1H, 2H, 2H-perfluorooctyl)pyridinium-4-yl]ethenyl}phenolate methanol disolvate, a fluoroponytailed solvatochromic dye10.1107/S2056989017013378 ↗
39. SHELXT—Integrated space-group and crystal-structure determination10.1107/S2053273314026370 ↗